Compounds for organic electronic elements, organic electronic elements using the compounds, and electronic devices thereof

Abstract

The present application provides a new compound capable of improving the light-emitting 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 application relates to a compound for an organic electronic element, an organic electronic element using the same, and an electronic device thereof. BACKGROUND

[0002] Generally, the organic light emitting phenomenon refers to a phenomenon that converts electrical energy into light energy by using an organic material. 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 multi-layer structure composed of different materials, and can include, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, etc.

[0003] A material used as an organic material layer in an organic electronic element can 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, etc., according to its function.

[0004] The service life and efficiency are the biggest problems of an organic electroluminescent device, and as a display becomes larger, these problems of efficiency and service life must be solved. The efficiency, service life, and driving voltage are related to each other, and when the efficiency increases, the driving voltage is relatively reduced, and as the driving voltage is reduced, the crystallization of an organic material due to Joule heating generated during driving is reduced, and thus the service life tends to increase.

[0005] However, it is not possible to maximize the efficiency 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 (mobility, interface properties, etc.) of the material are optimally combined, long service life and high efficiency can be simultaneously achieved.

[0006] In addition, in order to solve the light emission problem in the hole transport layer in the recent organic electroluminescent device, a light emission auxiliary layer must exist between the hole transport layer and the light emitting layer, and different light emission auxiliary layers should be developed according to each light emitting layer (R, G, B).

[0007] Generally, electrons are transferred from the electron transport layer to the light emitting layer, and holes are transferred from the hole transport layer to the light emitting layer, and excitons are generated by recombination.

[0008] However, since the material for the hole transport layer should have a low HOMO value, most of them have a low T1 value. As a result, the excitons generated in the light emitting layer are transferred to the hole transport layer, causing charge imbalance in the light emitting layer, thereby emitting light at the hole transport layer interface.

[0009] When light is emitted at the interface of the hole transport layer, the color purity and efficiency of the organic electronic element are reduced, and the service life is shortened. Therefore, there is an urgent need to develop a light-emitting auxiliary layer having a high T1 value and having a HOMO energy level between the HOMO energy level of the hole transport layer and the HOMO energy level of the light-emitting layer.

[0010] In addition, there is a need to develop a hole injection layer material that delays the penetration and diffusion of metal oxides from the anode electrode (ITO) to the organic layer, which is one of the reasons for shortening the service life of the organic electronic element, and has stable properties, i.e., a high glass transition temperature, even against the Joule heating generated during device driving. The low glass transition temperature of the hole transport layer material has the property of reducing the uniformity of the thin film surface during device driving, which is reported to have a significant impact on device service life. In addition, OLED devices are mainly formed by a deposition method, and there is a need to develop a material that can withstand long-term deposition, i.e., a material having strong heat resistance.

[0011] In other words, in order to fully exhibit the excellent properties of the organic electronic element, it is necessary to give priority to materials that are stable and effective materials for constituting the organic material layer in the device, such as a hole injection material, a hole transport material, a light-emitting material, an electron transport material, an electron injection material, a light-emitting auxiliary layer material, etc., but the development of stable and effective organic material layer materials for organic electronic devices has not been fully achieved. Therefore, there is a need to continuously develop new materials. SUMMARY

[0012] To solve the problems of the above background art, the present application discloses a compound having a new structure, and when the compound is applied to an organic electronic element, it has been found that the light-emitting efficiency, stability, and service life of the device can be significantly improved.

[0013] Therefore, the present application aims to provide a new compound, an organic electronic element using the same, and an electronic device thereof.

[0014] TECHNICAL SOLUTION

[0015] The present application provides a compound represented by Formula 1.

[0016] Formula 1

[0017]

[0018] In another aspect, the present application provides an organic electronic element comprising the compound represented by Formula 1, and an electronic device thereof.

[0019] EFFECT OF THE INVENTION

[0020] By using the compound according to the invention, high luminous efficiency, low driving voltage and high heat resistance of the device can be achieved, and the color purity and service life of the device can be greatly improved. Attached Figure Description

[0021] Figures 1 to 3 This is an exemplary view of an organic electroluminescent device according to the present invention.

[0022] Figure 4 The formula according to an aspect of the invention is shown.

[0023] Figure 5 The results of driving voltage measurements for hole mobility analysis of an organic electroluminescent device according to an aspect of the present invention are shown.

[0024] Figure 6 The HOMO electron clouds of compound C and compound P-55 of the present invention are shown. Detailed Implementation

[0025] Some embodiments of the invention will be described in detail below. Furthermore, in the following description of the invention, detailed descriptions of known functions and configurations incorporated herein will be omitted where such inclusion would make the subject matter of the invention considerably unclear.

[0026] Furthermore, when describing components of the present invention, terms such as first, second, A, B, (a), (b) may be used herein. Each of these terms is not intended to define the substance, order, or sequence of the respective component, but only to distinguish the respective component from other components. It should be noted that if a component is described as “connected,” “linked,” or “attached” to another component, the component may be directly connected to or connected to other components, but may be “connected,” “linked,” or “attached” between components.

[0027] As used in the specification and appended claims, unless otherwise stated, the following terms have the following meanings.

[0028] Unless otherwise stated, the term "halogenated" or "halogen" as used herein includes fluorine, bromine, chlorine, or iodine.

[0029] Unless otherwise stated, the term "alkyl" or "alkyl group" as used herein means having a single bond and 1 to 60 carbon atoms, and refers to a saturated aliphatic functional group, including straight-chain alkyl groups, branched alkyl groups, cycloalkyl groups (alicyclic), alkyl-substituted cycloalkyl groups, or cycloalkyl-substituted alkyl groups.

[0030] Unless otherwise stated, the term "alkenyl" or "alkynyl" as used herein has a double or triple bond and 2 to 60 carbon atoms, but is not limited thereto, and includes straight or branched groups.

[0031] The term "cycloalkyl" as used herein, unless otherwise indicated, means an alkyl group forming a ring having 3 to 60 carbon atoms, but is not limited thereto.

[0032] The term "alkoxy", "alkoxy group", or "alkyloxy" as used herein, unless otherwise indicated, means an oxy group attached to an alkyl group having 1 to 60 carbon atoms, but is not limited thereto.

[0033] The term "aryloxy group" or "aryloxy group" as used herein, unless otherwise indicated, means an oxy group attached to an aryl group having 6 to 60 carbon atoms, but is not limited thereto.

[0034] The term "aryl group" and "arylene group" used in the present invention, unless otherwise indicated, have 6 to 60 carbon atoms, but is not limited thereto. In the present invention, the aryl group or the arylene group means a monocyclic or polycyclic aromatic, and includes an aromatic ring formed by connecting or participating in the reaction of adjacent substituents.

[0035] For example, the aryl group can be a phenyl group, a biphenyl group, a fluorene group, or a spirofluorene group.

[0036] The prefix "aryl" or "ar" means a group substituted with an aryl group. For example, arylalkyl can be an alkyl group substituted with an aryl group, and arylalkenyl can be an alkenyl group substituted with an aryl group, and the number of carbon atoms of the group substituted with an aryl group has the number of carbon atoms as defined herein.

[0037] In addition, when the prefix is sequentially named, it means that the substituents are listed in the order of first described. For example, arylalkoxy means an alkoxy group substituted with an aryl group, alkoxycarbonyl means a carbonyl group substituted with an alkoxy group, and arylcarbonylalkenyl also means an alkenyl group substituted with an arylcarbonyl group, in which the arylcarbonyl group can be a carbonyl group substituted with an aryl group.

[0038] The term "heterocyclic group" as used herein, unless otherwise indicated, contains one or more heteroatoms, has 2 to 60 carbon atoms, but is not limited thereto, includes any one of a monocyclic and a polycyclic, and can include a heteroaliphatic ring and a heteroaromatic ring. In addition, it can also be combined with adjacent groups to form a heterocyclic group.

[0039] The term "heteroatom" as used herein, unless otherwise indicated, means at least one of N, O, S, P, or Si.

[0040] In addition, the term "heterocyclic group" can include a ring including SO2 instead of a carbon constituting the ring.

[0041] For example, the "heterocyclic group" includes the following compounds.

[0042]

[0043] Unless otherwise stated, the terms “fluorenyl group” or “fluoreneyl group” as used herein mean that R, R' and R” are all monovalent or divalent functional groups of hydrogen in the following structures, and the terms “substituted fluorenyl group” or “substituted fluoreneyl group” mean that at least one of the substituents R, R', and R” is a substituent other than hydrogen, and include those in which R and R' are bonded to each other to form a spiro compound together with the carbons they are bonded to.

[0044]

[0045] As used in this article, the term "spiro compound" has a "spiral connection," and a spiral connection means a connection in which two rings share only one atom. In this case, the atom shared by the two rings is called a "spiro atom," and these compounds are called "single-spiro," "double-spiro," and "triple-spiro," respectively, depending on the number of spiro atoms in the compound.

[0046] Unless otherwise stated, as used herein, the term "aliphatic" 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.

[0047] Unless otherwise stated, as used herein, the term "ring" means an aliphatic ring having 3 to 60 carbon atoms, an aromatic ring having 6 to 60 carbon atoms, a heterocyclic ring having 2 to 60 carbon atoms, or a fused ring formed by combination thereof, and includes saturated or unsaturated rings.

[0048] In addition to the hetero compounds mentioned above, other hetero compounds or heterogroups contain, but are not limited to, one or more hetero atoms.

[0049] Furthermore, unless explicitly stated otherwise, the term "substituted or unsubstituted" as used herein means substituted by one or more substituents selected from deuterium, halogens, amino groups, nitrile groups, nitro groups, C1-C6 groups, and C2-C4 groups. 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 group, deuterated C6-C 20aryl group, C8-C 20 arylalkyl group, silane group, boron group, germanium group, and C2-C 20 heterocyclic group, but are not limited to these substituents.

[0050] Further, unless explicitly explained, the formula used in the present invention is the same as the definition of the substituent defined by the index of the following formula.

[0051]

[0052] Here, when a is an integer of zero, the substituent R 1 is not present, when a is an integer of 1, the only substituent R 1 is connected to any one of the carbons constituting the benzene ring, when a is an integer of 2 or 3, each in the following combinations, wherein R 1 may be the same as or different from each other, when a is an integer of 4 to 6, it is bonded to the carbons of the benzene ring in a similar manner, but the indication of the hydrogen bonded to the carbon forming the benzene ring is omitted.

[0053]

[0054] Hereinafter, a compound according to an aspect of the present invention and an organic electronic element comprising the same will be described.

[0055] The present invention provides a compound represented by Formula 1.

[0056] Formula 1

[0057]

[0058] wherein each symbol can be defined as follows.

[0059] 1) R 1 , R 2 , R 3 , and R 4 are the same as or different from each other, and each is independently selected from the group consisting of hydrogen; deuterium; halogen; C6-C 60 aryl group; fluorenyl group; C2-C 60 heterocyclic group containing at least one heteroatom of O, N, S, Si, or P; C3-C 60 aliphatic ring; and C6-C 60 aromatic ring; C1-C 50 alkyl group; C2-C 20 alkenyl group; C2-C 20 alkynyl group; C1-C 30 alkoxy group; C6-C 30 aryloxy group; or a plurality of R 1 , or a plurality of R 2One or more R 3 One or more R 4 They can bond together to form a ring.

[0060] When R 1 R 2 R 3 and R 4 When it is an aryl group, it can preferably be C6-C. 30 Aryl group, and more preferably C6-C 25 The aryl group can be, for example, phenyl, biphenyl, naphthyl, terphenyl, etc.

[0061] When R 1 R 2 R 3 and R 4 When it is a heterocyclic group, it can preferably be C2-C. 30 Heterocyclic groups, and more preferably C2-C 24 Heterocyclic groups, for example, can be pyrazine, thiophene, pyridine, pyrimidindole, 5-phenyl-5H-pyrimidindole[5,4-b]indole, quinazoline, benzoquinazoline, carbazole, dibenzoquinazoline, dibenzofuran, dibenzothiophene, benzothiophene-pyrimidine, benzofuran-pyrimidine, benzothiazine, phenylbenzothiazine, etc.

[0062] When R 1 R 2 R 3 and R 4 When it is a fused ring group, it can preferably be C3-C. 30 Aliphatic rings and C6-C 30 Fused ring groups of aromatic rings, more preferably C3-C 24 Aliphatic rings and C6-C 24 Fused ring groups of aromatic rings.

[0063] When R 1 R 2 R 3 and R 4 When it is an alkyl group, it can preferably be C1-C. 30 Alkyl groups, and more preferably C1-C 24 Alkyl groups.

[0064] When R 1 R 2 R 3 and R 4 When the group is an alkoxy group, it can preferably be C1-C. 24 Alkoxy group.

[0065] When R 1 R 2 R3 and R 4 is an aryloxy group, it can preferably be a C1-C 24 aryloxy group.

[0066] 2) X and Y are independently of each other O or S,

[0067] 3) L 1 , L 2 and L 3 are each independently selected from a single bond; a C6-C 60 arylene group; a fluorenylene group; a C2-C 60 heterocyclic group comprising at least one heteroatom of O, N, S, Si or P; and a fused ring group of a C3-C 60 aliphatic ring and a C6-C 60 aromatic ring;

[0068] 4) L 4 is selected from a C6-C 60 arylene group; a fluorenylene group; a C2-C 60 heterocyclic group comprising at least one heteroatom of O, N, S, Si or P; and a fused ring group of a C3-C 60 aliphatic ring and a C6-C 60 aromatic ring;

[0069] wherein L 1 , L 2 , L 3 and L 4 is an arylene group, it can preferably be a C6-C 30 arylene group, more preferably a C6-C 24 arylene group, for example, phenylene, biphenylene, naphthylene, terphenylene, etc.

[0070] wherein L 1 , L 2 , L 3 and L 4 is a heterocyclic group, it can preferably be a C2-C 30 heterocyclic group, and more preferably a C2-C 24 heterocyclic group, for example, pyrazine, thiophene, pyridine, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, benzoquinazoline, carbazole, dibenzoquinazoline, dibenzofuran, dibenzothiophene, benzothienopyrimidine, benzofuranopyrimidine, benzothiazine, phenylbenzothiazine, etc.

[0071] wherein L 1 , L 2 , L 3 and L 4 is a fused ring group, it can preferably be a C3-C30 aliphatic ring and C6-C 30 aromatic ring, more preferably C3-C 24 aliphatic ring and C6-C 24 aromatic ring.

[0072] 5) Ar 1 , Ar 2 , Ar 3 , Ar 4 and Ar 5 are each independently selected from the group consisting of C6-C 60 aryl groups; fluorenyl groups; C2-C 60 heterocyclic groups; C3-C 60 aliphatic ring and C6-C 60 aromatic ring; C1-C 60 alkyl groups; C2-C 30 alkenyl groups; C2-C 20 alkynyl groups; C1-C 30 alkoxy groups; C6-C 30 aryloxy groups;

[0073] wherein Ar 1 , Ar 2 , Ar 3 , Ar 4 and Ar 5 are aryl groups, which can preferably be C6-C 30 aryl groups, most preferably C6-C 25 aryl groups, illustratively, they can be phenyl, biphenyl, naphthyl, terphenyl, etc.

[0074] wherein Ar 1 , Ar 2 , Ar 3 , Ar 4 and Ar 5 are heterocyclic groups, which can preferably be C2-C 30 heterocyclic groups, and more preferably C2-C 24 heterocyclic groups, for example, they can be pyrazine, thiophene, pyridine, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, benzoquinazoline, carbazole, dibenzoquinazoline, dibenzofuran, dibenzothiophene, benzothienopyrimidine, benzofuranopyrimidine, benzothiazine, phenylbenzothiazine, etc.

[0075] wherein Ar 1 , Ar 2 , Ar 3 , Ar 4and Ar 5 are fused ring groups, they can preferably be C3-C 30 aliphatic rings and C6-C 30 aromatic rings, more preferably C3-C 24 aliphatic rings and C6-C 24 aromatic rings.

[0076] wherein Ar 1 , Ar 2 , Ar 3 , Ar 4 and Ar 5 are alkyl groups, they can preferably be C1-C 30 alkyl groups, more preferably C1-C 24 alkyl groups.

[0077] wherein Ar 1 , Ar 2 , Ar 3 , Ar 4 and Ar 5 are alkoxy groups, they can preferably be C1-C 24 alkoxy groups.

[0078] wherein Ar 1 , Ar 2 , Ar 3 , Ar 4 and Ar 5 are aryloxy groups, they can preferably be C1-C 24 aryloxy groups.

[0079] 6) a and d are each independently an integer of 0 to 4, b and c are each independently an integer of 0 to 3, m and n are each independently 0 or 1, provided that m + n > 1;

[0080] 7) provided that when Formula 1 is a compound represented by Formula 7,

[0081] Formula 7

[0082]

[0083] 8) wherein R 1 , R 2 , R 3 , R 4 , X, Y, L 1 , L 2 , L 4 , Ar 1 , Ar 2 , Ar 3 , a, b and c are the same as defined in Formula 1, d' is an integer of 0 to 3,

[0084] 9) wherein the aryl group, the arylene group, the heterocyclic group, the fluorenyl group, the fluorenylene group, the aliphatic cyclic group, the fused ring group, the alkyl group, the alkenyl group, the alkoxy group and the aryloxy group can be substituted with one or more substituents selected from the group consisting of deuterium; a halogen; a silane group; a siloxane group; a boron group; a germanium group; a cyano group; a nitro group; a C1-C 20 alkylthio group; a C1-C 20 alkoxy group; a C1-C 20 alkyl group; a C2-C 20 alkenyl group; a C2-C 20 alkynyl group; a C6-C 20 aryl group; a C6-C 20 aryl group substituted with deuterium; a fluorenyl group; a C2-C 20 heterocyclic group; a C3-C 20 cycloalkyl group; a C7-C 20 arylalkyl group and a C8-C 20 arylalkenyl group; in addition, the substituents can be bonded to each other to form a saturated or unsaturated ring, wherein the term "ring" means a C3-C 60 aliphatic ring or a C6-C 60 aromatic ring or a C2-C 60 heterocyclic group or a fused ring formed by a combination thereof.

[0085] In addition, the present application provides a compound, wherein L 1 , L 2 , L 3 and L 4 is represented by any one of formulae b-1 to b-13.

[0086]

[0087] {wherein

[0088] 1) Z is O, S, C(R 13 )(R 14 ) or N-L 5 -Ar 6 ,

[0089] 2) Z 1 , Z 2 , Z 3 , Z 4 and Z 5 are each independently N or C(R 15 ), provided that Z 1 , Z 2 , Z 3 , Z 4 and Z5 At least one of them is C(R) 15 ), at least one of which is N;

[0090] 3)R 5 R 6 R 7 R 8 R 9 R 10 R 11 R 12 R 13 R 14 and R 15 With R in Equation 1 1 The definitions are the same, or adjacent groups can combine with each other to form a ring.

[0091] 4) e, g, h, and l are each independent integers from 0 to 4, f is an integer from 0 to 6, i and j are each independent integers from 0 to 3, and k is an integer from 0 to 2.

[0092] 5)Ar 6 Ar in Equation 1 1 The definitions are the same.

[0093] 6)L 5 With L in Equation 1 1 The definitions are the same.

[0094] 7) Indicates the binding position.

[0095] Furthermore, the compound represented by Formula 1 can be represented by any one of Formulas 1-1 to 1-3.

[0096]

[0097] {in

[0098] 1)R 1 R 2 R 3 R 4 X, Y, L 1 L 2 L 3 L 4 Ar 1 Ar 2 Ar 3 Ar 4 Ar 5 a, b, c, and d are the same as those defined in Equation 1.

[0099] 2) c' is an integer from 0 to 2, and d' is an integer from 0 to 3.

[0100] Further, the compound represented by Formula 1 is represented by any one of Formula 2-1 to Formula 2-4.

[0101]

[0102] {wherein

[0103] R 1 , R 2 , R 3 , R 4 , X, Y, L 1 , L 2 , L 3 , L 4 , Ar 1 , Ar 2 , Ar 3 , Ar 4 , Ar 5 , a, b, c, d, m, and n are the same as defined in Formula 1}

[0104] Further, the compound represented by Formula 1 is represented by any one of Formula 3-1 to Formula 3-14

[0105]

[0106]

[0107] {wherein

[0108] 1) R 1 , R 2 , R 3 , R 4 , X, Y, L 1 , L 2 , L 3 , L 4 , Ar 1 , Ar 2 , Ar 3 , Ar 4 , Ar 5 , a, b, c, and d are the same as defined in Formula 1,

[0109] 2) c' is an integer of 0 to 2, and d' is an integer of 0 to 3}

[0110] Further, the compound represented by Formula 1 is represented by any one of Formula 4-1 to Formula 4-6.

[0111]

[0112]

[0113] {wherein

[0114] 1) R 1 , R 2 , R 3 , R 4 , X, Y, L 1 , L 2 , L 3 , Ar 1 , Ar 2 , Ar 3 , Ar 4 , Ar 5 , a, b, c, d, m and n are the same as defined in Formula 1.

[0115] 2) R 5 , R 6 , R 7 , R 9 , R 10 , R 11 , R 12 , e, f, g, i, j, k, 1 and Z are the same as defined in Formula b-1 to Formula b-13.

[0116] Further, the compound represented by Formula 1 is represented by any one of Formula 5-1 to Formula 5-4

[0117]

[0118] {wherein

[0119] R 1 , R 2 , R 3 , R 4 , X, Y, L 1 , L 2 , L 3 , L 4 , Ar 1 , Ar 2 , Ar 3 , Ar 4 , Ar 5 , a, b, c, d, m and n are the same as defined in Formula 1.

[0120] Further, the compound represented by Formula 1 is represented by any one of Formula 6-1 to Formula 6-40

[0121]

[0122]

[0123]

[0124]

[0125]

[0126] {wherein,

[0127] 1) R 1 , R 2 , R 3 , R 4 , X, Y, L 1 , L 2 , L 3 , L 4 , Ar 1 , Ar 2 , Ar 3 , Ar 4 , Ar 5 , a, b, c, and d are the same as defined in Formula 1.

[0128] 2) c' is an integer of 0 to 2, and d' is an integer of 0 to 3.

[0129] Further, the compound represented by Formula 1 is represented by any one of the following compounds P-1 to compound P-152.

[0130]

[0131]

[0132]

[0133]

[0134]

[0135]

[0136]

[0137] Referring to Figure 1 The organic electronic element (100) according to the present application includes a first electrode (110), a second electrode (170), and an organic material layer including a single compound represented by Formula 1 or two or more compounds between the first electrode (110) and the second electrode (170). In this case, the first electrode (110) can be an anode, and the second electrode (170) can be a cathode. In the case of an inverted type, the first electrode can be a cathode, and the second electrode can be an anode.

[0138] The organic material layer can include, in order on the first electrode (110), 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). In this case, the remaining layers other than the light-emitting layer (140) can not be formed. It can also include a hole blocking layer, an electron blocking layer, a light-emitting auxiliary layer (220), a buffer layer (210), etc., and the electron transport layer (150) or the like can serve as a hole blocking layer. (See Figure 2 )

[0139] Further, the organic electronic element according to the embodiment of the present application can also include a protective layer or a light efficiency enhancement layer (180). The light efficiency enhancement layer can be formed on one surface of two surfaces of the first electrode which does not contact with the organic material layer, or on one surface of two surfaces of the second electrode which does not contact with the organic material layer. The compound according to the embodiment of the present application suitable for the organic material layer can 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 a dopant of a light-emitting layer (140), or as a material of a light efficiency enhancement layer. Preferably, for example, the compound according to Formula 1 of the present application can be used as a material of a light-emitting auxiliary layer or a light-emitting layer.

[0140] The organic material layer can include two or more stacks including a hole transport layer, a light-emitting layer, and an electron transport layer formed in order on an anode, and further including a charge generation layer formed between the two or more stacks (see Figure 3 ).

[0141] In addition, even in the case of the same core, the band gap, the electrical properties, the interface properties, etc. can vary depending on the position of the bonding of the substituent, and thus the selection of the combination of the core and the sub-substituent bonded thereto is also very important, and particularly, when the optimal combination of the energy level and the T1 value of each organic material layer and the unique properties of the material (mobility, interface properties, etc.) are achieved, long service life and high efficiency can be simultaneously achieved.

[0142] The organic electroluminescent device according to the embodiment of the present application can 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 an anode, and after forming 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) thereon, it can be prepared by depositing a material which can serve as a cathode thereon.

[0143] Further, in the present application, the organic material layer is formed by any one of a spin coating process, a nozzle printing process, an inkjet printing process, a slot coating process, a dip coating process, and a roll-to-roll process, and the organic material layer provides an organic electronic element including the compound as an electron transport material.

[0144] 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.

[0145] Further, the present application provides a light-emitting auxiliary layer composition including the compound represented by Formula 1, and provides an organic electronic element including the light-emitting auxiliary layer.

[0146] Further, the present application provides a hole transport layer composition including the compound represented by Formula 1, and provides an organic electronic element including the hole transport layer.

[0147] Further, the present application provides a light efficiency enhancement layer composition including the compound represented by Formula 1, and provides an organic electronic element including the light efficiency enhancement layer.

[0148] Further, the present application provides an electronic device including a display device including an organic electronic element; and a control unit for driving the display device.

[0149] In another aspect, the organic electronic element is at least one of an organic electroluminescent device, an organic solar cell, an organic photoreceptor, 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 controls, navigation units, game machines, various TVs, and various computers.

[0150] Hereinafter, a synthesis example of the compound represented by Formula (1) of the present application and a manufacturing example of the organic electronic element of the present application will be described in detail with reference to Examples, but the present application is not limited to the following Examples.

[0151] [Synthesis Example 1]

[0152] The compound represented by Formula 1 (final product) according to the present application can be prepared by reactions as shown in Scheme 1 below, but is not limited thereto. 1 to Hal 3 is I, Br, or Cl.

[0153] <Reaction Scheme 1>

[0154]

[0155] F = Ar 2 , Ar 3 , Ar 4

[0156] I. Synthesis of Sub-1

[0157] Sub-1 of Scheme 1 is synthesized by the following reaction path of Scheme 2 and Scheme 3, but is not limited thereto. Hal 1 to Hal 5 is I, Br or Cl.

[0158] <Reaction Scheme 2> If X is S

[0159]

[0160] <Reaction Scheme 3> If X is O

[0161]

[0162] 1. Synthesis of Sub-1-1

[0163]

[0164] (1) Synthesis of Sub-1-g-1

[0165] After Sub-1-e-1 (30.0 g, 60.5 mmol) was dissolved in THF (302 mL) in a round bottom flask, Sub-1-f-1 (12.1 g, 60.5 mmol), Pd(PPh3)4 (4.2 g, 3.6 mmol), NaOH (7.3 g, 181.4 mmol), H2O (151 mL) were added and stirred at 80°C. After the reaction was completed, the mixture was extracted with CH2Cl2 and water, the organic layer was dried over MgSO4, concentrated, and the resulting compound was recrystallized by a silica gel column to obtain 15.0 g of the product. (Yield: 69%)

[0166] (2) Synthesis of Sub-1-1

[0167] Sub-1-g-1 (15.0 g, 41.7 mmol) obtained was placed in a round bottom flask with Pd(OAc)2(0.5 g, 2.1 mmol) and 3-nitropyridine (0.3 g, 2.1 mmol), after being dissolved in C6F6(62 mL) and DMI (42 mL), tert-butyl peroxybenzoate (16.2 g, 83.4 mmol) was added and the mixture was stirred at 90°C. After the completion of the reaction, the mixture was extracted with CH2Cl2and water, the organic layer was dried over MgSO4, concentrated, and the resulting compound was recrystallized through a silica gel column to obtain 9.4 g of the product. (Yield: 63%)

[0168] 2. Synthesis of Sub-1-2

[0169]

[0170] (1) Synthesis of Sub-1-g-2

[0171] After placing Sub-1-e-2 (30.0 g, 105.8 mmol), THF (529 mL), Sub-1-f-2 (26.5 g, 105.8 mmol), Pd(PPh3)4(7.3 g, 6.4 mmol), NaOH (12.7 g, 317.4 mmol), H2O (265 mL) in a round bottom flask, 29.0 g of the product was obtained in the same manner as Sub-1-g-1 at 80°C. (Yield: 67%)

[0172] (2) Synthesis of Sub-1-2

[0173] Sub-1-g-2 (29.0 g, 70.9 mmol) obtained was dissolved in a round bottom flask, after adding Pd(OAc)2(0.8 g, 3.5 mmol), 3-nitropyridine (0.4 g, 3.5 mmol), C6F6(106 mL), DMI (71 mL), tert-butyl peroxybenzoate (27.5 g, 141.8 mmol), 17.9 g of the product was obtained by performing the experiment in the same manner as Sub-1-1 at 90°C. (Yield: 62%)

[0174] 3. Synthesis of Sub-1-55

[0175]

[0176] (1) Synthesis of Sub-1-c-55

[0177] After Sub-1-a-55 (30.0 g, 106.0 mmol) was dissolved in THF (530 mL) in a round bottom flask, Sub-1-b-55 (29.5 g, 106.0 mmol), Pd(PPh3)4(7.4 g, 6.4 mmol), NaOH (12.7 g, 318.1 mmol), H2O (265 mL) were added and stirred at 80°C. After the reaction was completed, the mixture was extracted with CH2Cl2and water, the organic layer was dried over MgSO4, concentrated, and the resulting compound was recrystallized on a silica gel column to obtain 33.1 g of the product. (Yield: 80%)

[0178] (2) Synthesis of Sub-1-d-55

[0179] Sub-1-c-55 (33.1 g, 84.8 mmol), H2O2(8.5 mL), and acetic acid (339 mL) were placed in a round bottom flask and stirred at room temperature. When the reaction was completed, the acetic acid was removed and water was added to obtain a solid, and the solid was dissolved in CH2Cl2and concentrated on a silica gel column to obtain 30.6 g of the product. (Yield: 89%)

[0180] (3) Synthesis of Sub-1-55

[0181] Sub-1-d-55 (30.6 g, 405.73 mmol) was dissolved in excess H2SO4(91.9 mL) in a round bottom flask, followed by stirring at room temperature for 6 hours. When the reaction was completed, the reaction was neutralized using an aqueous NaOH solution, extracted with CH2Cl2, the organic layer was dried over MgSO4, concentrated, and the resulting compound was recrystallized on a silica gel column to obtain 24.3 g of the product. (Yield: 86%)

[0182] 4. Synthesis of Sub-1-83

[0183]

[0184] (1) Synthesis of Sub-1-c-83

[0185] After Sub-1-a-83 (30.0 g, 147.1 mmol), THF (735 mL), Sub-1-b-83 (41.4 g, 147.1 mmol), Pd(PPh3)4(10.2 g, 8.8 mmol), NaOH (17.7 g, 441.2 mmol), H2O (368 mL) were placed in a round bottom flask, the experiment was performed in the same manner as Sub-1-g-1 at 80°C to obtain 33.2 g of the product. (Yield: 72%)

[0186] (2) Synthesis of Sub-1-d-83

[0187] Sub-1-c-83 (33.2 g, 105.9 mmol), H2O2 (10.6 mL), acetic acid (424 mL) were placed in a round bottom flask and tested in the same manner as Sub-1-d-55 at room temperature to obtain 31.4 g of product. (Yield: 90%)

[0188] (3) Synthesis of Sub-1-83

[0189] Sub-1-d-83 (31.4 g, 95.3 mmol) and H2SO4 (94.2 mL) were added and dissolved, followed by the same experiment as Sub-1-55 to obtain 25.0 g of product. (Yield: 88%)

[0190] 5. Synthesis of Sub-1-97

[0191]

[0192] (1) Synthesis of Sub-1-g-97

[0193] After Sub-1-e-97 (30.0 g, 100.4 mmol), THF (502 mL), Sub-1-f-97 (36.0 g, 100.4 mmol), Pd(PPh3)4 (7.0 g, 6.0 mmol), NaOH (12.0 g, 301.1 mmol), H2O (251 mL) were placed in a round bottom flask, the experiment was performed in the same manner as Sub-1-g-1 above at 80°C to obtain 34.1 g of product. (Yield: 70%)

[0194] (2) Synthesis of Sub-1-97

[0195] After Sub-1-g-97 (34.1 g, 70.3 mmol) was dissolved in a round bottom flask, Pd(OAc)2 (0.8 g, 3.5 mmol), 3-nitropyridine (0.4 g, 3.5 mmol), C6F6 (105 mL), DMI (70 mL), t-butyl peroxybenzoate (27.3 g, 140.5 mmol) were added and the experiment was performed in the same manner as Sub-1-1 above at 90°C. 21.1 g of product was obtained.

[0196] (Yield: 63%)

[0197] 6. Synthesis of Sub-1-114

[0198]

[0199] (1) Synthesis of Sub-1-c-114

[0200] After Sub-1-a-114 (30.0 g, 149 mmol), THF (750 mL), Sub-1-b-114 (42.5 g, 149 mmol), Pd(PPh3)4 (10.4 g, 8.96 mmol), NaOH (17.9 g, 448 mmol), and H2O (375 mL) were placed in a round bottom flask, the experiment was performed in the same manner as Sub-1-g-1 at 80°C to obtain 39.4 g of product. (Yield: 84%)

[0201] (2) Synthesis of Sub-1-d-114

[0202] Sub-1-c-114 (39.4 g, 126 mmol), H2O2 (35.9 mL), and acetic acid (500 mL) were placed in a round bottom flask, and the experiment was performed in the same manner as Sub-1-d-55 at room temperature to obtain 38.1 g of product. (Yield: 92%)

[0203] (3) Synthesis of Sub-1-d-114

[0204] Sub-1-d-114 (38.1 g, 115 mmol) and H2SO4 (114 mL) were added and dissolved, and then the same procedure as Sub-1-55 was performed to obtain 30.2 g of product. (Yield: 88%)

[0205] 7. Synthesis Example of Sub-1-127

[0206]

[0207] (1) Synthesis of Sub-1-g-127

[0208] After Sub-1-e-127 (30.0 g, 127 mmol), THF (640 mL), Sub-1-f-127 (31.6 g, 127 mmol), Pd(PPh3)4 (8.82 g, 7.63 mmol), NaOH (15.3 g, 382 mmol), H2O (320 mL) were placed in a round bottom flask, the experiment was performed in the same manner as Sub-1-g-1 at 80°C to obtain 35.7 g of product. (Yield: 78%)

[0209] (2) Synthesis of Sub-1-127

[0210] After Sub-1-g-127 (35.7 g, 99.2 mmol) was dissolved in a round-bottom flask, Pd(OAc)2 (1.11 g, 4.96 mmol), 3-nitropyridine (0.62 g, 4.96 mmol), C6F6 (148 mL), DMI (99 mL), t-butyl peroxybenzoate (38.5 g, 198 mmol) were added, and tested in the same manner as Sub-1-1 at 90°C to obtain 14.9 g of product. (Yield: 42%)

[0211] 8. Synthesis Example of Sub-1-131

[0212]

[0213] (1) Synthesis of Sub-1-c-131

[0214] After Sub-1-a-131 (30.0 g, 157 mmol), THF (780 mL), Sub-1-b-131 (38.7 g, 157 mmol), Pd(PPh3)4 (10.9 g, 9.40 mmol), NaOH (18.8 g, 470 mmol), H2O (390 mL) were placed in a round-bottom flask, the experiment was performed in the same manner as Sub-1-g-1 at 80°C to obtain 40.3 g of product. (Yield: 82%)

[0215] (2) Synthesis of Sub-1-d-131

[0216] Sub-1-c-131 (40.3 g, 129 mmol), H2O2 (36.7 mL), and acetic acid (515 mL) were placed in a round-bottom flask, and tested in the same manner as Sub-1-d-55 at room temperature to obtain 38.5 g of product. (Yield: 91%)

[0217] (3) Synthesis of Sub-1-131

[0218] Sub-1-d-131 (38.5 g, 117 mmol) and H2SO4 (116 mL) were added and dissolved, and then the same experiment as Sub-1-55 was performed to obtain 32.4 g of product. (Yield: 93%)

[0219] 9. Synthesis of Sub-1-132

[0220]

[0221] (1) Synthesis of Sub-1-g-132

[0222] After Sub-1-f-132 (30.0 g, 72.2 mmol), THF (360 mL), Sub-1-e-132 (10.0 g, 72.2 mmol), Pd(PPh3)4 (5.0 g, 4.33 mmol), NaOH (8.7 g, 217 mmol), H2O (180 mL) were placed in a round-bottom flask, the experiment was performed at 80°C by the same manner as Sub-1-g-1 to obtain 18.7 g of product. (Yield: 72%)

[0223] (2) Synthesis of Sub-1-132

[0224] After Sub-1-g-132 (18.7 g, 52.0 mmol) was dissolved in a round-bottom flask, Pd(OAc)2 (0.58 g, 2.60 mmol), 3-nitropyridine (0.32 g, 2.60 mmol), C6F6 (78 mL), DMI (52 mL), tert-butyl peroxybenzoate (20.2 g, 104 mmol) were added, and tested at 90°C in the same manner as Sub-1-1 to obtain 12.6 g of product. (Yield: 68%)

[0225] 10. Synthesis Example of Sub-1-133

[0226]

[0227] (1) Synthesis of Sub-1-c-133

[0228] After Sub-1-a-133 (30.0 g, 192 mmol), THF (960 mL), Sub-1-b-133 (63.1 g, 192 mmol), Pd(PPh3)4 (13.3 g, 11.5 mmol), NaOH (23.0 g, 576 mmol), H2O (480 mL) were placed in a round-bottom flask, the experiment was performed at 80°C by the same manner as Sub-1-g-1 to obtain 48.1 g of product. (Yield: 80%)

[0229] (2) Synthesis of Sub-1-d-133

[0230] Sub-1-c-133 (48.1 g, 154 mmol), H2O2 (43.9 mL), and acetic acid (614 mL) were placed in a round-bottom flask, and at room temperature, 44.5 g of product was obtained in the same manner as Sub-1-d-55. (Yield: 88%)

[0231] (3) Synthesis of Sub-1-133

[0232] Sub-1-d-133 (44.5 g, 135 mmol) and H2SO4 (134 mL) were added and dissolved, followed by the same experiment as Sub-1-55 to obtain 36.6 g of the product. (Yield: 91%)

[0233] The compound belonging to Sub-1 can be the following compound, but is not limited thereto, and the following

[0234] Table 1 shows the field desorption-mass spectrometry (FD-MS) values of the compound belonging to Sub-1.

[0235]

[0236]

[0237]

[0238]

[0239]

[0240] [Table 1]

[0241]

[0242]

[0243]

[0244]

[0245] II. Synthesis of Sub-2

[0246] Sub-2 of Scheme 1 was synthesized by the following reaction path of Scheme 4, but is not limited thereto. Hal 6 is I, Br or Cl.

[0247] <Reaction Scheme 4>

[0248]

[0249] In Reaction Scheme 4, E and F are as defined in Scheme 1.

[0250] 1. Synthesis Example of Sub-2-2

[0251]

[0252] After Sub-2-a-2 (20.0 g, 177.7 mmol), Sub-2-b-2 (44.5 g, 177.7 mmol), Pd2(dba)3 (4.9 g, 5.3 mmol), P(t-Bu)3 (2.2 g, 10.7 mmol), NaOt-Bu (34.2 g, 355.4 mmol), toluene (888 mL) were put in a round bottom flask, the reaction was performed 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. Then, the resulting organic material was recrystallized through a silica gel column to obtain 45.3 g of the product. (Yield 76%)

[0253] 2. Synthesis example of Sub-2-3

[0254]

[0255] Sub-2-a-2 (20.0 g, 177.7 mmol), Sub-2-b-3 (70.9 g, 177.7 mmol), Pd2(dba)3 (4.9 g, 5.3 mmol), P(t-Bu)3 (2.2 g, 10.7 mmol), NaOt-Bu (34.2 g, 355.4 mmol), toluene (888 mL) were tested in a round bottom flask in the same manner as Sub-2-2 to obtain 30.0 g of the product.

[0256] (Yield: 77%)

[0257] 3. Synthesis example of Sub-2-94

[0258]

[0259] Sub-2-a-94 (20.0 g, 83.8 mmol), Sub-2-b-2 (21.0 g, 83.8 mmol), Pd2(dba)3 (2.3 g, 2.5 mmol), P(t-Bu)3 (1.0 g, 5.0 mmol), NaOt-Bu (16.1 g, 167.6 mmol), toluene (419 mL) were tested in a round bottom flask in the same manner as Sub-2-2 to obtain 30.2 g of the product. (Yield: 78%)

[0260] 4. Synthesis example of Sub-2-96

[0261]

[0262] Sub-2-a-96 (20.0 g, 63.5 mmol), Sub-2-b-2 (15.9 g, 63.5 mmol), Pd2(dba)3 (1.8 g, 1.9 mmol), P(t-Bu)3 (0.8 g, 3.8 mmol), NaOt-Bu (12.2 g, 127.1 mmol), toluene (318 mL) were tested in a round bottom flask in the same manner as Sub-2-2 to obtain 26.3 g of product. (Yield: 77%)

[0263] 5. Synthesis example of Sub-2-114

[0264]

[0265] Sub-2-a-2 (20.0 g, 177.7 mmol), Sub-2-b-114 (5.4 g, 60.3 mmol), Pd2(dba)3 (4.9 g, 5.3 mmol), P(t-Bu)3 (2.2 g, 10.7 mmol), NaOt-Bu (34.2 g, 355.4 mmol), toluene (888 mL) were tested in a round bottom flask in the same manner as Sub-2-2 to obtain 56.4 g of product. (Yield: 79%)

[0266] 6. Synthesis example of Sub-2-156

[0267]

[0268] Sub-2-a-156 (30.0 g, 88.4 mmol), aniline (8.2 g, 88.4 mmol), Pd2(dba)3 (2.43 g, 2.65 mmol), P(t-Bu)3 (1.07 g, 5.31 mmol), NaOt-Bu (17.0 g, 177 mmol), toluene (440 mL) were tested in a round bottom flask in the same manner as Sub-2-2 to obtain 22.4 g of product. (Yield: 72%)

[0269] 7. Synthesis example of Sub-2-159

[0270]

[0271] Sub-2-a-159 (30.0 g, 88.4 mmol), aniline (8.2 g, 88.4 mmol), Pd2(dba)3 (2.43 g, 2.65 mmol), P(t-Bu)3 (1.07 g, 5.31 mmol), NaOt-Bu (17.0 g, 177 mmol), toluene (440 mL) were tested in a round bottom flask in the same manner as Sub-2-2 to obtain 21.4 g of product. (Yield: 69%)

[0272] 8. Synthesis example of Sub-2-162

[0273]

[0274] Sub-2-a-162 (30.0 g, 92.8 mmol), aniline (8.6 g, 92.8 mmol), Pd2(dba)3 (2.55 g, 2.78 mmol), P(t-Bu)3 (1.13 g, 5.57 mmol), NaOt-Bu (17.8 g, 186 mmol), toluene (465 mL) were tested in a round bottom flask in the same manner as Sub-2-2 to obtain 23.4 g of product. (Yield: 75%)

[0275] The compounds belonging to Sub-2 can be the following compounds, but are not limited thereto, and Table 2 below shows FD-MS (Field Desorption-Mass Spectrometry) values of the compounds belonging to Sub-2.

[0276]

[0277]

[0278]

[0279]

[0280]

[0281]

[0282]

[0283] [Table 2]

[0284]

[0285]

[0286]

[0287]

[0288]

[0289] III. Synthesis of final product

[0290] 1. Synthesis of P-1

[0291]

[0292] (1) Synthesis of Inter-1-1

[0293] After Sub-1-1 (20.0 g, 55.9 mmol), Sub-2-1 (9.1 g, 55.9 mmol), Pd2(dba)3 (1.5 g, 1.7 mmol), P(t-Bu)3 (0.7 g, 3.4 mmol), NaOt-Bu (10.7 g, 111.8 mmol), toluene (280 mL) were placed in a round bottom flask, the reaction was performed 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. Then, the resulting organic material was recrystallized through a silica gel column to obtain 17.5 g of the product. (Yield 70%)

[0294] (2) Synthesis of P-1

[0295] After Inter-1-1 (10.0 g, 22.4 mmol), Sub-2-2 (7.3 g, 22.4 mmol), Pd2(dba)3 (0.6 g, 0.7 mmol), P(t-Bu)3 (0.3 g, 1.4 mmol), NaOt-Bu (4.3 g, 44.8 mmol), toluene (112 mL) were placed in a round bottom flask, 10.3 g of the product was obtained in the same manner as Inter-1-1 by performing the experiment at 80°C. (Yield: 71%)

[0296] 2. Synthesis example of P-2

[0297]

[0298] (1) Synthesis of Inter-1-2

[0299] After Sub-1-2 (20.0 g, 49.1 mmol), Sub-2-3 (10.4 g, 49.1 mmol), Pd2(dba)3 (1.4 g, 1.5 mmol), P(t-Bu)3 (0.6 g, 2.9 mmol), NaOt-Bu (9.4 g, 98.1 mmol), and toluene (245 mL) were placed in a round bottom flask, 18.2 g of a product was obtained by conducting an experiment at 80°C in the same manner as Inter-1-1 above. (Yield: 68%)

[0300] (2) Synthesis of P-2

[0301] After Inter-1-2 (10.0 g, 18.3 mmol), Sub-2-2 (5.9 g, 18.3 mmol), Pd2(dba)3 (0.5 g, 0.6 mmol), P(t-Bu)3 (0.2 g, 1.1 mmol), NaOt-Bu (3.5 g, 36.6 mmol), toluene (92 mL) were placed in a round bottom flask, 10.5 g of a product was obtained by conducting an experiment at 80°C in the same manner as Inter-1-1 above. (Yield: 68%)

[0302] 3. Synthesis Example of P-49

[0303]

[0304] (1) Synthesis of Inter-1-49

[0305] After Sub-1-49 (10.0 g, 21.6 mmol), Sub-2-1 (3.6 g, 21.6 mmol), Pd2(dba)3 (0.59 g, 0.65 mmol), P(t-Bu)3 (0.26 g, 1.29 mmol), NaOt-Bu (4.1 g, 43.1 mmol), toluene (108 mL) were placed in a round bottom flask, 8.5 g of a product was obtained by conducting an experiment at 80°C in the same manner as Inter-1-1 above. (Yield: 71%)

[0306] (2) Synthesis of P-49

[0307] After Sub-1-49 (8.5 g, 15.3 mmol), Sub-2-50 (6.3 g, 15.3 mmol), Pd2(dba)3 (0.42 g, 0.46 mmol), P(t-Bu)3 (0.19 g, 0.92 mmol), NaOt-Bu (2.9 g, 30.6 mmol), toluene (77 mL) were placed in a round bottom flask, 10.2 g of the product was obtained by conducting the experiment at 80°C in the same manner as Inter-1-1 above. (Yield: 72%)

[0308] 4. Synthesis Example of P-55

[0309]

[0310] (1) Synthesis of Inter-1-55

[0311] After Sub-1-55 (20.0 g, 53.5 mmol), Sub-2-1 (8.8 g, 53.5 mmol), Pd2(dba)3 (1.5 g, 1.6 mmol), P(t-Bu)3 (0.7 g, 3.2 mmol), NaOt-Bu (10.3 g, 107.0 mmol), toluene (268 mL) were placed in a round bottom flask, 17.6 g of the product was obtained by conducting the experiment at 80°C in the same manner as Inter-1-1 above. (Yield: 71%)

[0312] (2) Synthesis of P-55

[0313] After Inter-1-55 (10.0 g, 21.6 mmol), Sub-2-2 (7.0 g, 21.6 mmol), Pd2(dba)3 (0.6 g, 0.7 mmol), P(t-Bu)3 (0.3 g, 1.3 mmol), NaOt-Bu (4.2 g, 43.3 mmol), toluene (108 mL) were placed in a round bottom flask, 11.9 g of the product was obtained by conducting the experiment at 80°C in the same manner as Inter-1-1 above. (Yield: 72%)

[0314] 5. Synthesis Example of P-83

[0315]

[0316] (1) Synthesis of Inter-1-83

[0317] After Sub-1-83 (20.0 g, 67.2 mmol), Sub-2-1 (11.6 g, 25.9 mmol), Pd2(dba)3 (1.9 g, 2.0 mmol), P(t-Bu)3 (0.8 g, 4.0 mmol), NaOt-Bu (12.9 g, 134.4 mmol), toluene (336 mL) were placed in a round-bottom flask, 17.4 g of the product was obtained by conducting the experiment at 80°C in the same manner as Inter-1-1 above. (Yield: 67%)

[0318] (2) Synthesis of P-83

[0319] After Inter-1-83 (10.0 g, 25.9 mmol), Sub-2-94 (11.6 g, 25.9 mmol), Pd2(dba)3 (0.7 g, 0.8 mmol), P(t-Bu)3 (0.3 g, 1.6 mmol), NaOt-Bu (5.0 g, 51.8 mmol), toluene (130 mL) were placed in a round-bottom flask, 14.5 g of the product was obtained by conducting the experiment at 80°C in the same manner as Inter-1-1 above. (Yield: 69%)

[0320] 6. Synthesis Example of P-97

[0321]

[0322] (1) Synthesis of Inter-1-97

[0323] After Sub-1-97 (20.0 g, 41.4 mmol), Sub-2-114 (16.0 g, 41.4 mmol), Pd2(dba)3 (1.1 g, 1.2 mmol), P(t-Bu)3 (0.5 g, 2.5 mmol), NaOt-Bu (8.0 g, 82.7 mmol), toluene (207 mL) were placed in a round-bottom flask, 22.5 g of the product was obtained by conducting the experiment at 80°C in the same manner as Inter-1-1 above. (Yield: 72%)

[0324] (2) Synthesis of P-2-97

[0325] After Inter-1-97 (15.0 g, 19.8 mmol), Sub-2-1 (3.2 g, 19.8 mmol), Pd2(dba)3 (0.5 g, 0.6 mmol), P(t-Bu)3 (0.2 g, 1.2 mmol), NaOt-Bu (3.8 g, 39.6 mmol), toluene (99 mL) were placed in a round bottom flask, 12.6 g of the product was obtained by conducting the experiment at 80°C in the same manner as Inter-1-1 above. (Yield: 75%)

[0326] (3) Synthesis of P-97

[0327] After Inter-2-97 (10.0 g, 11.8 mmol), Sub-2-5 (4.0 g, 11.8 mmol), Pd2(dba)3 (0.3 g, 0.4 mmol), P(t-Bu)3 (0.1 g, 0.7 mmol), NaOt-Bu (2.3 g, 23.7 mmol), toluene (59 mL) were placed in a round bottom flask, 9.7 g of the product was obtained by conducting the experiment at 80°C in the same manner as Inter-1-1 above. (Yield: 71%)

[0328] 7. Synthesis Example of P-129

[0329]

[0330] (1) Synthesis of Inter-1-129

[0331] After Sub-1-112 (10.0 g, 35.5 mmol), Sub-2-162 (11.9 g, 35.5 mmol), Pd2(dba)3 (0.98 g, 1.07 mmol), P(t-Bu)3 (0.43 g, 2.13 mmol), NaOt-Bu (6.8 g, 71.0 mmol), toluene (178 mL) were placed in a round bottom flask, 14.1 g of the product was obtained by conducting the experiment at 80°C in the same manner as Inter-1-1 above. (Yield: 74%)

[0332] (2) Synthesis of P-129

[0333] After placing Inter-1-129 (14.1 g, 26.3 mmol), Sub-2-1 (4.4 g, 26.3 mmol), Pd2(dba)3 (0.72 g, 0.79 mmol), P(t-Bu)3 (0.32 g, 1.58 mmol), NaOt-Bu (5.1 g, 52.6 mmol), and toluene (131 mL) in a round-bottom flask, 12.3 g of the product was obtained by conducting the experiment at 80 °C in the same manner as with Inter-1-1 above. (Yield: 70%)

[0334] 8. Synthesis example of P-133

[0335]

[0336] (1) Synthesis of Inter-1-133

[0337] After placing Sub-1-131 (40.0 g, 134 mmol), Sub-2-1 (22.7 g, 134 mmol), Pd2(dba)3 (3.69 g, 4.03 mmol), P(t-Bu)3 (1.63 g, 8.06 mmol), NaOt-Bu (25.8 g, 269 mmol), and toluene (672 mL) in a round-bottom flask, 40.5 g of the product was obtained by conducting the experiment at 80 °C in the same manner as with Inter-1-1 above. (Yield: 78%)

[0338] (2) Synthesis of P-133

[0339] After placing Inter-1-133 (15.0 g, 38.9 mmol), Sub-2-2 (13.0 g, 38.9 mmol), Pd2(dba)3 (1.07 g, 1.17 mmol), P(t-Bu)3 (0.47 g, 2.33 mmol), NaOt-Bu (7.5 g, 77.7 mmol), and toluene (194 mL) in a round-bottom flask, 19.4 g of the product was obtained by conducting the experiment at 80 °C in the same manner as with Inter-1-1 above. (Yield: 73%)

[0340] 9. Example of P-134 synthesis

[0341]

[0342] (1) Synthesis of Inter-1-134

[0343] After Sub-1-125 (10.0 g, 26.8 mmol), Sub-2-1 (4.5 g, 26.8 mmol), Pd2(dba)3 (0.74 g, 0.80 mmol), P(t-Bu)3 (0.32 g, 1.61 mmol), NaOt-Bu (5.1 g, 53.5 mmol), toluene (134 mL) were placed in a round bottom flask, 8.4 g of the product was obtained by conducting the experiment at 80°C in the same manner as Inter-1-1 above. (Yield: 68%)

[0344] (2) Synthesis of P-134

[0345] After Inter-1-134 (8.4 g, 18.2 mmol), Sub-2-2 (6.1 g, 18.2 mmol), Pd2(dba)3 (0.50 g, 0.55 mmol), P(t-Bu)3 (0.22 g, 1.09 mmol), NaOt-Bu (3.5 g, 36.4 mmol), toluene (91 mL) were placed in a round bottom flask, 9.3 g of the product was obtained by conducting the experiment at 80°C in the same manner as Inter-1-1 above. (Yield: 67%)

[0346] 10. Synthesis Example of P-150

[0347]

[0348] After Inter-1-133 (25.0 g, 64.8 mmol), Sub-2-5 (22.8 g, 64.8 mmol), Pd2(dba)3 (1.78 g, 1.94 mmol), P(t-Bu)3 (0.79 g, 3.89 mmol), NaOt-Bu (12.5 g, 130 mmol), toluene (324 mL) were placed in a round bottom flask, 33.1 g of the product was obtained by conducting the experiment at 80°C in the same manner as Inter-1-1 above. (Yield: 73%)

[0349] 11. Synthesis Example of P-152

[0350]

[0351] The obtained P-150 (15.0 g, 21.4 mmol) was dissolved in perdeuterated benzene (C6D6) (161.8 g, 1926 mmol), CF3SO3D (16.1 g, 107 mmol) was added, and then reacted at 80°C for 3 hours to form deuterated material. Periodically sampled and measured the degree of deuterium by LC-MS. After the deuterium exchange reaction was completed at the desired substitution rate, it was cooled to room temperature, quenched by adding a D2O solution of Na2CO3, and the organic solvent was concentrated. Recrystallization was performed using toluene and acetone solvents to obtain 14.1 g (yield: 90%) of deuterated compound P-152. The final mass was determined by LC-MS to confirm that it was 85.2% deuterated.

[0352] Meanwhile, FD-MS values of the compounds P-1 to P-152 of the present application prepared according to the above synthesis example are shown in Table 3 below.

[0353] [Table 3]

[0354]

[0355]

[0356]

[0357]

[0358] Evaluation of organic electronic element manufacturing

[0359] [Example 1] Red organic light emitting device (light emitting auxiliary layer)

[0360] An organic electroluminescent device was produced according to a conventional method using the compound of the present application as a light-emitting auxiliary layer material. First, after a 4,4',4"-tris[2-naphthyl(phenyl)amino]triphenylamine (abbreviated as 2-TNATA) was vacuum-deposited to a thickness of 60 nm on an ITO layer (anode) formed on a glass substrate to form a hole injection layer, on the hole injection layer, N,N'-bis(1-naphthyl)-N,N'-bis-phenyl-(1,1'-biphenyl)-4,4'-diamine (abbreviated as NPB) was vacuum-deposited to a thickness of 60 nm as a hole transport compound to form a hole transport layer. Then, after the compound P-1 of the present application was vacuum-deposited to a thickness of 40 nm on the hole transport layer to form a light-emitting auxiliary layer, on the light-emitting auxiliary layer, by using 4,4'-N,N'-dicarbazole-biphenyl (abbreviated as CBP) doped at a weight ratio of 95:5 as a host material and bis(1-phenylisoquinolyl)iridium(III) acetylacetonate (hereinafter, referred to as (piq)2Ir(acac)) as a dopant, a light-emitting layer was formed by vacuum-depositing to a thickness of 30 nm on the light-emitting auxiliary layer. Then, (1,1'-biphenyl-4-ylidene)bis(2-methyl-8-quinolinolato)aluminum (hereinafter, referred to as BAIq) was vacuum-deposited to a thickness of 5 nm on the light-emitting layer to form a hole blocking layer, and bis(10-hydroxybenzo[h]quinolinolato)beryllium (hereinafter, referred to as BeBq2) was vacuum-deposited to a thickness of 35 nm on the hole blocking layer to form an electron transport layer. Then, an alkali metal halide LiF was deposited to a thickness of 0.2 nm on the electron transport layer as an electron injection layer, and then, Al was deposited to a thickness of 150 nm on the electron injection layer and served as a cathode, to produce an organic electroluminescent device.

[0361] [Examples 2] to [Example 23]

[0362] An organic electroluminescent device was produced in the same manner as in Example 1, but the compound of the present application described in Table 4 was used instead of the compound P-1 of the present application as a light-emitting auxiliary layer material.

[0363] [Comparative Example 1]

[0364] An organic electroluminescent device was produced in the same manner as in Example 1, but the light-emitting auxiliary layer was not formed.

[0365] [Comparative Examples 2] to [Comparative Example 6]

[0366] An organic electroluminescent device was produced in the same manner as in Example 1, but Comparative Compound A to Comparative Compound E were used instead of the compound P-1 of the present application as a light-emitting auxiliary layer material.

[0367]

[0368]

[0369] Electroluminescence (EL) characteristics were measured with PR-650 from photo research by applying a forward-biased DC voltage to the organic electroluminescent devices prepared in Examples and Comparative Examples in this manner, and as a result of the measurement, a lifespan measuring device manufactured by McScience was used to measure the lifespan at 2500 cd / m 2 The standard luminance measurement T95 lifespan. Table 4 below shows the device manufacturing and evaluation results.

[0370] [Table 4]

[0371]

[0372]

[0373]

[0374] Referring to Table 4, when a red organic light emitting device was manufactured using the material for an organic electroluminescent device of the present application as a light emitting auxiliary layer material, the driving voltage, luminous efficiency, and lifespan of the organic electroluminescent device were significantly improved compared to the comparative examples in which no light emitting auxiliary layer was formed or in which Comparative Compound A to Comparative Compound E was used.

[0375] In other words, in Comparative Examples 2 to 6 in which Comparative Compound A to Comparative Compound E was used as a light emitting auxiliary layer instead of Comparative Example 1 in which no light emitting auxiliary layer was formed, the driving voltage, efficiency, and lifespan of the device were improved, and when the compound of the present application was used as a material for a light emitting auxiliary layer, the driving voltage of the organic electroluminescent device was reduced compared to when Comparative Compound A to Comparative Compound E was used as a light emitting auxiliary layer, and the luminous efficiency and lifespan were improved.

[0376] Comparing Comparative Compound A or Comparative Compound E to the compound of the present application, the structures in which dibenzofuran or dibenzothiophene is bonded between amines are the same, but the compound of the present application has a structure in which dibenzofuran or dibenzothiophene is further substituted with an amine group. Therefore, the refractive index when dibenzofuran or dibenzothiophene is bonded to an amine group is significantly higher than when substituted with a general aryl group substituent, and the Tg also increases, so the efficiency and thermal stability are excellent.

[0377] In addition, the compound of the present application is the same as Comparative Compound B in that an amine group substitutes dibenzofuran or dibenzothiophene, but is different in that a linking group between dibenzofuran or dibenzothiophene and the amine group is necessarily present.

[0378] Accordingly, the compound of the present application is different from the comparative compound by introducing a linking group between dibenzofuran or dibenzothiophene and an amine group, so that the conjugation length becomes longer than that of the comparative compound B, thus improving the hole property, and therefore significantly increasing the driving and efficiency, and increasing the chemical stability of the non-shared electron pair, and also increasing the service life, compared to the comparative compound.

[0379] Comparative compound C and the compound of the present application were compared, which are the same structure as the compound of the present application, but the bonding position of dibenzothiophene between amine and amine is 3 and 7, and the position of dibenzothiophene bonded to amine is 3-substituted. Figure 6 The HOMO electron cloud of comparative compound C and the compound P-55 of the present application is shown.

[0380] Reference Figure 6 In the case of comparative compound C, the electron cloud is widely distributed on two amine moieties, but as can be seen, the compound of the present application forms an electron cloud in a narrower region than that of the comparative compound, and in this way, the hole mobility is improved and the device properties are determined to be affected.

[0381] Further, in order to confirm that the hole mobility is improved, an organic electronic device was manufactured with an ITO layer (anode) / 2-TNATA 60 nm / NPB 60 nm / comparative compound C or the compound P-55 of the present application / HATCN 10 nm / Al (cathode) 150 nm and HOD (hole-only device), and the current density-voltage characteristics were measured by Figure 5 and the results are confirmed in Table 5 below.

[0382] [Table 5]

[0383]

[0384] Reference Figure 5 As can be seen from Table 5, at a current density of 0.1 mA / cm 2 , the driving voltage of comparative compound C was 2.19 V, while the driving voltage of the compound P-55 of the present application was 0.61 V, and the difference between comparative compound C and the compound P-55 of the present application was 1.58 V. Further, at a current density of 10 mA / cm 2 , the driving voltage of comparative compound C was 2.97 V, while the driving voltage of the compound P-55 of the present application was 1.35 V, and it can be seen that the difference between comparative compound C and the compound P-55 of the present application was 1.62 V. From this, it can be seen that the compound of the present application has a more improved hole mobility compared to comparative compound C.

[0385] That is, based on the above points, it can be judged that the compound of the present application shows superior device characteristics compared to Comparative Compound C.

[0386] Comparative Compound D and the compound of the present application were compared, Comparative Compound D has a structure in which a fluorene group is introduced between amines, while the compound of the present application has a structure in which a dibenzofuran or dibenzothiophene is bonded between amines. It can be confirmed that the refractive index when a dibenzofuran or dibenzothiophene is introduced is significantly higher than the refractive index when a fluorene group is introduced, and the Tg also increases, thereby improving the efficiency and thermal stability.

[0387] In summary, although Comparative Compounds A to E and the compound of the present application are composed of similar components, the introduction of a linking group between the dibenzofuran or dibenzothiophene and the amine group makes the properties of the compound, such as hole characteristics, light efficiency characteristics, hole injection and mobility characteristics, charge balance of holes and electrons, more suitable for a red light-emitting auxiliary layer, so the device results of Examples 1 to 23 are significantly superior to those of Comparative Examples 2 to 6.

[0388] In the case of a light-emitting auxiliary layer, since the correlation between the hole transport layer and the light-emitting layer (host) needs to be understood, it is difficult to infer the properties of the light-emitting auxiliary layer using the compound of the present application even for those skilled in the art, even if a similar core is used.

[0389] In addition, in the evaluation results of the above device manufacturing, the device characteristics have been described in which only the compound of the present application is applied to the light-emitting auxiliary layer, but the compound of the present application can be applied to the hole transport layer, or can be applied to both the hole transport layer and the light-emitting auxiliary layer.

[0390] Although exemplary embodiments of the present application are described for illustrative purposes, those skilled in the art will understand that various modifications, additions and substitutions are possible, without departing from the scope and spirit of the present application as disclosed in the appended claims. Therefore, the embodiments disclosed in the present application are intended to illustrate the scope of the technical idea of the present application, and the scope of the present application is not limited by the embodiments. The scope of the present application should be interpreted based on the appended claims, and should be interpreted to include all technical ideas within the scope equivalent to the claims. BRIEF DESCRIPTION OF DRAWINGS

[0392] 100, 200, 300: organic electronic element 110: first electrode

[0393] 120: hole injection layer 130: hole transport layer

[0394] 140: light-emitting layer 150: electron transport layer

[0395] 160: electron injection layer 170: second electrode

[0396] 180: light efficiency enhancement layer 210: buffer layer

[0397] 220: light emission auxiliary layer 320: first hole injection layer

[0398] 330: first hole transport layer 340: first light emission layer

[0399] 350: first electron transport layer 360: first charge generation layer

[0400] 361: second charge generation layer 420: second hole injection layer

[0401] 430: second hole transport layer 440: second light emission layer

[0402] 450: second electron transport layer CGL: charge generation layer

[0403] ST1: first stack ST2: second stack

Claims

1. A compound represented by Formula 3-2: Formula 3-2 wherein 1) R 1 , R 2 , R 3 , and R 4 are the same or different from each other and are each independently selected from hydrogen; deuterium, 2) X and Y are independently of each other O or S, 3) L 2 is selected from a single bond and a phenylene group, and L 3 is a single bond, 4) L 4 represented by formula b-1 : Formula b-1 in Formula b-1 a) R 5 is hydrogen; or deuterium, b) e is an integer of 0 to 4, 5) Ar 3 , Ar 4 , and Ar 5 each independently is a phenyl group; a biphenyl group; or a naphthyl group, 6) a and d are each independently an integer of 0 to 4, b is an integer of 0 to 3, and c' is an integer of 0 to 2; 7) wherein the phenylene group, phenyl group, biphenyl group, and naphthyl group can be substituted with one or more substituents selected from the group consisting of deuterium; a phenyl group.

2. The compound of claim 1, wherein the compound represented by Formula 3-2 is represented by any one of Formulae 6-33 to 6-36: Formula 6-33 Formula 6-34 Formula 6-35 Formula 6-36 wherein, R 1 , R 2 , R 3 , R 4 , X, Y, L 2 , L 3 , L 4 , Ar 3 , Ar 4 , Ar 5 , a, b, c' and d are the same as defined in formula 1.

3. A compound represented by any one of the following compounds: 。 4. 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 one or two or more of the compounds of claim 1 or 3.

5. The organic electronic element of claim 4, wherein the organic material layer comprises at least one of a hole injection layer, a hole transport layer, a light-emitting layer, a light-emitting auxiliary layer, an electron transport auxiliary layer, an electron transport layer, and an electron injection layer.

6. The organic electronic element of claim 4, wherein the organic material layer is a light-emitting auxiliary layer.

7. The organic electronic element of claim 4, wherein the organic material layer is a hole transport layer.

8. The organic electronic element of claim 4, further comprising a light efficiency enhancement layer formed on at least one surface of the surfaces of the anode and the cathode opposite to the organic material layer.

9. The organic electronic element of claim 4, wherein the organic material layer is a light efficiency enhancement layer.

10. The organic electronic element of claim 4, wherein the organic material layer comprises at least two or more stacks comprising a hole transport layer, a light-emitting layer, and an electron transport layer formed in this order on the anode.

11. The organic electronic element of claim 10, wherein the organic material layer further comprises a charge generation layer formed between the two or more stacks.

12. An electronic device comprising: A display device comprising the organic electronic element of claim 4; and a control unit for driving the display device.

13. The electronic device of claim 12, wherein the electronic device is any one of an organic electroluminescent device, an organic solar cell, an organic photoreceptor, an organic transistor, and an element for monochrome or white illumination.

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