Compound for organic electronic element, organic electronic element using same, and electronic device thereof

Abstract

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

Description

[0001] Division Explanation

[0002] This application is a divisional application of Patent Application No. 202111515321.1, titled "Compound for Organic Electronic Components, Organic Electronic Components Using the Compound, and Electronic Devices Thereof", filed on December 13, 2021, which is incorporated herein by reference in its entirety. Technical Field

[0003] The present invention relates to a compound for organic electronic components, an organic electronic component using the compound, and an electronic device thereof. Background Art

[0004] Generally, organic luminescence refers to the phenomenon of converting electrical energy into light energy by using organic materials. Organic electronic components using organic luminescence usually have 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 component, the organic material layer is usually composed of a multilayer structure made 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, etc.

[0005] The materials used as the organic material layer in organic electronic components 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.

[0006] Service life and efficiency are the biggest problems of organic electroluminescent devices, and as the displays become larger, these problems of efficiency and service life must be solved. Efficiency, service life, and driving voltage are interrelated. When the efficiency increases, the driving voltage relatively decreases. As the driving voltage decreases, the crystallization of the organic material due to Joule heating generated during driving decreases, and thus the service life tends to increase.

[0007] However, the efficiency cannot be simply maximized by improving the organic material layer. This is because long service life and high efficiency can be achieved simultaneously only when the energy levels and T1 values between the organic material layers and the inherent properties of the materials (mobility, interface properties, etc.) are optimally combined.

[0008] In addition, in order to solve the light-emitting problem in the hole transport layer of recent organic electroluminescent devices, a light-emitting auxiliary layer must be present between the hole transport layer and the light-emitting layer, and different light-emitting auxiliary layers should be developed according to each light-emitting layer (R, G, B).

[0009] Generally, electrons transfer from the electron transport layer to the light-emitting layer, and holes transfer from the hole transport layer to the light-emitting layer, and excitons are generated through recombination.

[0010] However, since the materials 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, leading to charge imbalance in the light-emitting layer and thus light emission at the interface of the hole transport layer.

[0011] When light emission occurs at the interface of the hole transport layer, the color purity and efficiency of the organic electronic device are reduced, and the service life is shortened. Therefore, there is an urgent need to develop a light-emitting auxiliary layer that has a high T1 value and a HOMO energy level between the HOMO energy level of the hole transport layer and the HOMO energy level of the light-emitting layer.

[0012] In addition, it is necessary 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 (such penetration and diffusion are one of the reasons for shortening the service life of organic electronic devices), and has stable properties, that is, a high glass transition temperature, and even resists the Joule heating generated during device operation. The low glass transition temperature of the hole transport layer material has the characteristic of reducing the uniformity of the film surface during device operation, which is reported to have a significant impact on the device service life. In addition, 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.

[0013] In other words, in order to fully exhibit the excellent characteristics of organic electronic devices, materials such as hole injection materials, hole transport materials, light-emitting materials, electron transport materials, electron injection materials, light-emitting auxiliary layer materials, etc., which are composed of stable and effective materials and are competent for forming the organic material layer in the device, should be given priority. However, the development of stable and effective organic material layer materials for organic electronic devices has not been fully realized. Therefore, it is necessary to continuously develop new materials. Summary of the Invention

[0014] To solve the problems in the above background art, the present invention discloses a compound with a new structure, and when this compound is applied to an organic electronic device, it has been found that the light-emitting efficiency, stability, and service life of the device can be significantly improved.

[0015] Therefore, the object of the present invention is to provide a new compound, an organic electronic device using the compound, and an electronic device thereof.

[0016] Technical Solution

[0017] The present invention provides a compound represented by Formula 1.

[0018] Formula 1

[0019]

[0020] On the other hand, the present invention provides an organic electronic element and an electronic device including the compound represented by Formula 1.

[0021] Advantages of the Invention

[0022] By using the compound according to the present invention, high luminous efficiency, low driving voltage, and high heat resistance of the device can be achieved, and the color purity and service life of the device can be greatly improved. BRIEF DESCRIPTION OF THE DRAWINGS

[0023] Figures 1 to 3 is an exemplary view of an organic electroluminescent device according to the present invention.

[0024] Figure 4 shows a formula according to an aspect of the present invention.

[0025] Figure 5 shows the driving voltage measurement results for hole mobility analysis of an organic electroluminescent device according to an aspect of the present invention.

[0026] Figure 6 shows the HOMO electron cloud comparing Compound C and Compound P-55 of the present invention DETAILED DESCRIPTION

[0027] 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.

[0028] In addition, when describing 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 define the essence, 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 "connected", "coupled", or "joined" to another component, the component may be directly connected or joined to the other component, but another component may be "connected", "coupled", or "joined" between the components.

[0029] As used in the specification and the appended claims, unless otherwise specified, the following are the meanings of the following terms.

[0030] Unless otherwise specified, the term "halo" or "halogen" as used herein includes fluorine, bromine, chlorine, or iodine.

[0031] Unless otherwise specified, the term "alkyl" or "alkyl group" as used herein has a single bond and from 1 to 60 carbon atoms and refers to a saturated aliphatic functional group, including straight-chain alkyl groups, branched-chain alkyl groups, cycloalkyl groups (alicyclic), cycloalkyl groups substituted with alkyl groups, or alkyl groups substituted with cycloalkyl groups.

[0032] Unless otherwise specified, the term "alkenyl" or "alkynyl" as used herein has a double bond or triple bond and from 2 to 60 carbon atoms, but is not limited thereto, and includes straight-chain or branched-chain groups.

[0033] Unless otherwise specified, the term "cycloalkyl" as used herein means an alkyl group forming a ring having from 3 to 60 carbon atoms, but is not limited thereto.

[0034] Unless otherwise specified, the term "alkoxy", "alkoxy group" or "alkyloxy" as used herein means an oxygen atom linked to an alkyl group having from 1 to 60 carbon atoms, but is not limited thereto.

[0035] Unless otherwise specified, the term "aryloxy group" or "aryloxy" as used herein means an oxygen atom linked to an aryl group having from 6 to 60 carbon atoms, but is not limited thereto.

[0036] Unless otherwise specified, the terms "aryl group" and "arylene group" used in the present invention have from 6 to 60 carbon atoms, but are not limited thereto. In the present invention, an aryl group or arylene group means a monocyclic or polycyclic aromatic group and includes aromatic rings formed by connection or participation in a reaction of adjacent substituents.

[0037] For example, an aryl group may be a phenyl group, a biphenyl group, a fluorene group or a spirofluorene group.

[0038] The prefix "aryl" or "ar" means a group substituted with an aryl group. For example, arylalkyl may be an alkyl group substituted with an aryl group, and arylalkenyl may be an alkenyl group substituted with an aryl group, and the group substituted with an aryl group has the number of carbon atoms as defined herein.

[0039] Furthermore, when the prefixes are named in sequence, this means that the substituents are listed in the order described first. 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, wherein arylcarbonyl may be a carbonyl group substituted with an aryl group.

[0040] 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 either monocyclic or polycyclic, and may include heteroaliphatic rings and heteroaromatic rings. In addition, it may also combine with adjacent groups to form a heterocyclic group.

[0041] Unless otherwise specified, the term "heteroatom" as used herein means at least one of N, O, S, P or Si.

[0042] In addition, the term "heterocyclic group" may include a ring containing SO2 in place of the carbon constituting the ring.

[0043] For example, the "heterocyclic group" includes the following compounds.

[0044]

[0045] 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'' are all hydrogen in the following structure, 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.

[0046]

[0047] The term "spiro compound" as used herein has "spiro linkage", and spiro linkage 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 "monospiro-", "dispiro-" and "trispiro-" according to the number of spiro atoms in the compound.

[0048] 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.

[0049] 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 heterocycle having 2 to 60 carbon atoms, or a fused ring formed by their combination, and includes a saturated ring or an unsaturated ring.

[0050] In addition to the hetero compounds mentioned above, other hetero compounds or hetero groups contain, but are not limited to, one or more heteroatoms.

[0051] In addition, unless otherwise specified, "substituted" in 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 group, C1-C 20 alkoxy group, C1-C 20 alkylamine group, C1-C 20 alkylthiophene group, C6-C 20 arylthiophene group, C2-C 20 alkenyl group, C2-C 20 alkynyl group, C3-C 20 cycloalkyl group, C6-C 20 aryl group, C6-C aryl group substituted by deuterium, C8-C 20 aryl group, C8-C 20 arylethenyl group, silyl group, boron group, germanium group and C2-C 20 heterocyclic group, but not limited to these substituents.

[0052] In addition, unless otherwise explicitly explained, the definitions of the substituents defined by the indices in the formulas used in the present invention are the same as those of the following formulas.

[0053]

[0054] Here, when a is an integer of zero, the substituent R 1 does not exist. When a is an integer of 1, the only substituent R 1 is attached to any of the carbons constituting the benzene ring. When a is an integer of 2 or 3, they are combined as follows respectively, where R 1 can be the same as or different from each other. When a is an integer from 4 to 6, they are 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.

[0055]

[0056] Hereinafter, compounds according to aspects of the present invention and organic electronic elements containing the compounds will be described.

[0057] The present invention provides a compound represented by Formula 1.

[0058] Formula 1

[0059]

[0060] Wherein, each symbol can be defined as follows.

[0061] 1) R 1 、R 2 、R 3 and R4 Same as or different from each other, and each independently selected from hydrogen; deuterium; halogen; C6-C 60 aryl group; fluorenyl group; C2-C containing at least one heteroatom of O, N, S, Si or P 60 heterocyclic group; C3-C 60 aliphatic ring and C6-C 60 fused ring group of 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 multiple adjacent Rs 1 、or multiple Rs 2 、or multiple Rs 3 、or multiple Rs 4 may bond to each other to form a ring.

[0062] When R 1 、R 2 、R 3 and R 4 are aryl groups, it may preferably be a C6-C 30 aryl group, and more preferably a C6-C 25 aryl group. For example, it may be phenyl, biphenyl, naphthyl, terphenyl, etc.

[0063] When R 1 、R 2 、R 3 and R 4 are heterocyclic groups, it may preferably be a C2-C 30 heterocyclic group, and more preferably a C2-C 24 heterocyclic group. For example, it may be pyrazine, thiophene, pyridine, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, benzquinazoline, carbazole, dibenzquinazoline, dibenzofuran, dibenzothiophene, benzothienopyrimidine, benzofuranopyrimidine, benzothiazine, phenylbenzothiazine, etc.

[0064] When R 1 、R 2 、R 3 and R 4 are fused ring groups, it may preferably be a C3-C 30 aliphatic ring and C6-C 30 fused ring group of aromatic ring, and more preferably a C3-C 24 aliphatic ring and C6-C 24 fused ring group of aromatic ring.

[0065] When R 1 、R 2 、R 3 and R 4 are alkyl groups, it may preferably be a C1-C 30 alkyl group, and more preferably a C1-C 24 alkyl group.

[0066] When R 1 、R 2 、R 3 and R 4 are alkoxy groups, it may preferably be a C1-C 24 alkoxy group.

[0067] When R 1 、R 2 、R 3 and R 4 are aryloxy groups, it may preferably be a C1-C 24 aryloxy group.

[0068] 2) X and Y are independently O or S from each other,

[0069] 3) L 1 、L 2 and L 3 each independently selected from a single bond; a C6-C 60 arylene group; a fluorenylene group; a C2-C 60 heterocyclic group containing at least one heteroatom of O, N, S, Si or P; and a C3-C 60 aliphatic ring and a C6-C 60 fused ring group of an aromatic ring;

[0070] 4) L 4 is selected from a C6-C 60 arylene group; a fluorenylene group; a C2-C 60 heterocyclic group containing at least one heteroatom of O, N, S, Si or P; and a C3-C 60 aliphatic ring and a C6-C 60 fused ring group of an aromatic ring;

[0071] wherein L 1 、L 2 、L 3 and L 4 are arylene groups, it may preferably be a C6-C 30 arylene group, more preferably a C6-C 24 arylene group, for example, phenylene, biphenyl, naphthalene, terphenyl, etc.

[0072] wherein L 1 、L2 , L 3 and L 4 is a heterocyclic group, which may preferably be C2 to C 30 Heterocyclic group, and more preferably C2 to C 24 Heterocyclic groups, for example, pyrazine, thiophene, pyridine, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, benzoquinazoline, carbazole, dibenzoquinazoline, dibenzofuran, dibenzothiophene, benzothienopyrimidine, benzofuropyrimidine, benzothiazine, phenylbenzothiazine, and the like.

[0073] Where L 1 , L 2 , L 3 and L 4 is a fused ring group, which may preferably be C3-C 30 Aliphatic ring and C6-C 30 Aromatic ring fused ring group, more preferably C3-C 24 Aliphatic ring and C6-C 24 Aromatic ring fused ring group.

[0074] 5)Ar 1 ,Ar 2 ,Ar 3 ,Ar 4 and Ar 5 Each independently selected from C6-C 60 Aryl group; Fluorenyl group; C2-C2 containing at least one heteroatom of O, N, S, Si or P 60 Heterocyclic group; C3-C 60 Aliphatic ring and C6-C 60 Aromatic ring fused ring group; C1-C 60 Alkyl group; C2~C 30 Alkenyl group; C2-C 20 Alkynyl group; C1-C 30 Alkoxy group; C6-C 30 aryloxy groups;

[0075] Among them, Ar 1 ,Ar 2 ,Ar 3 ,Ar 4 and Ar 5 are aryl groups, which may preferably be C6-C 30 Aryl groups, most preferably C6-C 25 Aryl groups, for example, may be phenyl, biphenyl, naphthyl, terphenyl, and the like.

[0076] Among them, Ar 1 ,Ar 2, Ar 3 , Ar 4 and Ar 5 When they are heterocyclic groups, they may preferably be C2-C 30 heterocyclic groups, and more preferably C2-C 24 heterocyclic groups. For example, they may be pyrazine, thiophene, pyridine, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, benzoquinazoline, carbazole, dibenzoquinazoline, dibenzofuran, dibenzothiophene, benzothienopyrimidine, benzofuranopyrimidine, benzothiazine, phenylbenzothiazine, etc.

[0077] Wherein Ar 1 , Ar 2 , Ar 3 , Ar 4 and Ar 5 When they are fused ring groups, they may preferably be C3-C 30 aliphatic ring and C6-C 30 fused ring group of aromatic ring, more preferably C3-C 24 aliphatic ring and C6-C 24 fused ring group of aromatic ring.

[0078] Wherein Ar 1 , Ar 2 , Ar 3 , Ar 4 and Ar 5 When they are alkyl groups, they may preferably be C1-C 30 alkyl groups, more preferably C1-C 24 alkyl groups.

[0079] Wherein Ar 1 , Ar 2 , Ar 3 , Ar 4 and Ar 5 When they are alkoxy groups, they may preferably be C1-C 24 alkoxy groups.

[0080] Wherein Ar 1 , Ar 2 , Ar 3 , Ar 4 and Ar 5 When they are aryloxy groups, they may preferably be C1-C 24 aryloxy groups.

[0081] 6) a and d are each independently an integer from 0 to 4, b and c are each independently an integer from 0 to 3, and m and n are each independently 0 or 1, provided that m + n ≥ 1;

[0082] 7) provided that when Formula 1 is a compound represented by Formula 7,

[0083] Formula 7

[0084]

[0085] 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 those defined in Formula 1, and d' is an integer from 0 to 3,

[0086] 9) wherein the aryl group, arylene group, heterocyclic group, fluorenyl group, fluorenylene group, aliphatic ring group, fused ring group, alkyl group, alkenyl group, alkoxy group and aryloxy group can be substituted by one or more substituents selected from deuterium; halogen; silyl group; siloxy group; boron group; germanium group; cyano group; nitro group; C1-C 20 alkylthio group; C1-C 20 alkoxy group; C1-C 20 alkyl group; C2-C 20 alkenyl group; C2-C 20 alkynyl group; C6-C 20 aryl group; C6-C aryl group substituted by deuterium; fluorenyl group; C2-C 20 heterocyclic group; C3-C 20 cycloalkyl group; C7-C 20 arylalkyl group and 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 20 aliphatic ring or a C6-C 60 aromatic ring or a C2-C 60 heterocyclic group or a fused ring formed by their combination. 60 In addition, the present invention provides a compound wherein L

[0087] 、L 1 、L 2 、L 3 and L 4 is represented by any one of Formula b-1 to Formula b-13.

[0088]

[0089] {Wherein

[0090] 1) Z is O, S, C(R 13 )(R 14 ), or N-L 5 -Ar 6 ,

[0091] 2) Z 1 , Z 2 , Z 3 , Z 4 , and Z 5 are each independently N or C(R 15 ), provided that at least one of Z 1 , Z 2 , Z 3 , Z 4 , and Z 5 is C(R 15 ), and at least one is N;

[0092] 3) R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , and R 15 are as defined for R 1 in Formula 1, or adjacent groups may combine with each other to form a ring,

[0093] 4) e, g, h, and l are each independently an integer from 0 to 4, f is an integer from 0 to 6, i and j are each independently an integer from 0 to 3, and k is an integer from 0 to 2,

[0094] 5) Ar 6 is as defined for Ar 1 in Formula 1,

[0095] 6) L 5 is as defined for L 1 in Formula 1,

[0096] 7) represents the bonding position.}

[0097] In addition, the compound represented by Formula 1 is represented by any one of Formulas 1-1 to 1-3

[0098]

[0099] {Wherein

[0100] 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,

[0101] 2) c' is an integer from 0 to 2, and d' is an integer from 0 to 3.}

[0102] In addition, the compound represented by Formula 1 is represented by any one of Formulas 2-1 to 2-4.

[0103]

[0104]

[0105] {where

[0106] 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}

[0107] In addition, the compound represented by Formula 1 is represented by any one of Formulas 3-1 to 3-14

[0108]

[0109]

[0110] {where

[0111] 1) R 1 、R 2 、R 3 、R 4 、X, Y, L 1 、L 2 、L3 、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,

[0112] 2) c' is an integer from 0 to 2, and d' is an integer from 0 to 3}

[0113] In addition, the compound represented by Formula 1 is represented by any one of Formulas 4-1 to 4-6.

[0114]

[0115]

[0116] {where

[0117] 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,

[0118] 2) R 5 、R 6 、R 7 、R 9 、R 10 、R 11 、R 12 、e, f, g, i, j, k, l, and Z are the same as defined in Formulas b-1 to b-13.}

[0119] In addition, the compound represented by Formula 1 is represented by any one of Formulas 5-1 to 5-4

[0120]

[0121]

[0122] {where

[0123] 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 those defined in Formula 1.}

[0124] In addition, the compound represented by Formula 1 is represented by any one of Formulas 6-1 to 6-40

[0125]

[0126]

[0127]

[0128]

[0129]

[0130] {Wherein,

[0131] 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 Formula 1.}

[0132] 2) c' is an integer from 0 to 2, and d' is an integer from 0 to 3.}

[0133] In addition, the compound represented by Formula 1 is represented by any one of Compound P-1 to Compound P-152 below.

[0167]

[0168]

[0169]

[0136]

[0137]

[0138]

[0139]

[0140]

[0141] Reference Figure 1 , the organic electronic device (100) according to the present invention includes a first electrode (110), a second electrode (170), and an organic material layer containing 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) 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.

[0142] The organic material layer may sequentially 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 this case, the remaining layers except the light-emitting layer (140) may not be formed. It may 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) etc. may be used as a hole blocking layer. (See Figure 2 )

[0143] In addition, the organic electronic device according to an embodiment of the present invention may further include a protective layer or a light efficiency enhancing layer (180). The light efficiency enhancing layer may be formed on one surface of the two surfaces of the first electrode that does not contact the organic material layer, or formed on one surface of the two surfaces of the second electrode that does not contact the organic material layer. The compound according to an embodiment of the present invention applicable to the organic material layer may be used as a host or a dopant of the hole injection layer (120), the hole transport layer (130), the light-emitting auxiliary layer (220), the electron transport auxiliary layer, the electron transport layer (150), and the electron injection layer (160), the light-emitting layer (140), or as a material of the light efficiency enhancing layer. Preferably, for example, the compound according to Formula 1 of the present invention may be used as a material of the light-emitting auxiliary layer or the light-emitting layer.

[0144] The organic material layer may include two or more stacked bodies, including a hole transport layer, a light-emitting layer, and an electron transport layer sequentially formed on the anode, and further includes a charge generation layer formed between the two or more stacked bodies (see Figure 3 )

[0145] In addition, even in the case of the same core, the band gap, electrical properties, interface properties, etc. can vary depending on the position where the substituent is bonded. Therefore, the selection of the combination of the core and the sub-substituents bonded thereto is also very important. In particular, when an optimal combination of the energy level, T1 value, and unique material properties (mobility, interface properties, etc.) of each organic material layer is achieved, long service life and high efficiency can be achieved simultaneously.

[0146] The organic electroluminescent device according to an embodiment of the present invention can be manufactured using a PVD (Physical Vapor Deposition) method. For example, a conductive metal, metal oxide, or 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 that can be used as a cathode thereon.

[0147] [[ID=⑧]]In addition, 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 slot 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.

[0148] As another specific example, the same or different compounds represented by Formula 1 are mixed and used in the organic material layer.

[0149] In addition, the present invention provides a luminescence assisting layer composition containing the compound represented by Formula 1, and provides an organic electronic element including the luminescence assisting layer.

[0150] In addition, the present invention provides a hole transport layer composition containing the compound represented by Formula 1, and provides an organic electronic element including the hole transport layer.

[0151] In addition, the present invention provides a light efficiency enhancing layer composition containing the compound represented by Formula 1, and provides an organic electronic element including the light efficiency enhancing layer.

[0152] In addition, the present invention provides an electronic device including a display device containing an organic electronic element; and a control unit for driving the display device.

[0153] On the other hand, 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 monochromatic or white illumination. At this time, the electronic device may 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 consoles, various TVs, and various computers.

[0154] Hereinafter, a synthesis example of the compound represented by the 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 the embodiments, but the present invention is not limited to the following embodiments.

[0155] [Synthesis Example 1]

[0156] The compound (final product) represented by Formula 1 according to the present invention can be prepared by the reaction shown in Scheme 1 below, but is not limited thereto. Hal 1 to Hal 3 is I, Br, or Cl.

[0157] [Reaction Scheme 1]

[0158]

[0159] I. Synthesis of Sub-1

[0160] Sub-1 of Scheme 1 is synthesized through the reaction paths of Scheme 2 and Scheme 3 below, but is not limited thereto. Hal 1 to Hal 5 is I, Br, or Cl.

[0161] [Reaction Scheme 2] If X is S

[0162]

[0163] [Reaction Scheme 3] If X is O

[0164]

[0165] 1. Synthesis of Sub-1-1

[0166]

[0167] (1) Synthesis of Sub-1-g-1

[0168] After dissolving Sub-1-e-1 (30.0 g, 60.5 mmol) 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), and H2O (151 mL) were added and the mixture was 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 through a silica gel column to obtain 15.0 g of the product. (Yield: 69%)

[0169] (2) Synthesis of Sub-1-1

[0170] The obtained Sub-1-g-1 (15.0 g, 41.7 mmol) 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 dissolving 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 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 through a silica gel column to obtain 9.4 g of the product. (Yield: 63%)

[0171] 2. Synthesis of Sub-1-2

[0172]

[0173] (1) Synthesis of Sub-1-g-2

[0174] 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), and H2O (265 mL) in a round-bottom flask, 29.0 g of the product was obtained at 80 °C in the same manner as Sub-1-g-1. (Yield: 67%)

[0175] (2) Synthesis of Sub-1-2

[0176] The obtained Sub-1-g-2 (29.0 g, 70.9 mmol) 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), and tert-butyl peroxybenzoate (27.5 g, 141.8 mmol), 17.9 g of the product was obtained in the same manner as Sub-1-1 by conducting the experiment at 90 °C. (Yield: 62%)

[0177] 3. Synthesis of Sub-1-55

[0178]

[0179] (1) Synthesis of Sub-1-c-55

[0180] After dissolving Sub-1-a-55 (30.0 g, 106.0 mmol) 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, 3,18.1 mmol), and H2O (265 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 through a silica gel column to obtain 33.1 g of the product. (Yield: 80%)

[0181] (2) Synthesis of Sub-1-d-55

[0182] 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, acetic acid was removed and water was added to obtain a solid, and the solid was dissolved in CH2Cl2 and concentrated on a silica gel column to obtain 30.6 g of the product. (Yield: 89%)

[0183] (3) Synthesis of Sub-1-55

[0184] Sub-1-d-55 (30.6 g, 405.73 mmol) was dissolved in an excess of H2SO4 (91.9 mL) in a round-bottom flask and then stirred at room temperature for 6 hours. When the reaction was completed, the reaction was neutralized with an aqueous NaOH solution, extracted with CH2Cl2, the organic layer was dried over MgSO4, concentrated, and the resulting compound was recrystallized through a silica gel column to obtain 24.3 g of the product. (Yield: 86%)

[0185] 4. Synthesis of Sub-1-83

[0186]

[0187] (1) Synthesis of Sub-1-c-83

[0188] After placing 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), and H2O (368 mL) in a round-bottom flask, the experiment was carried out at 80 °C in the same manner as Sub-1-g-1 to obtain 33.2 g of the product. (Yield: 72%)

[0189] (2) Synthesis of Sub-1-d-83

[0190] Sub-1-c-83 (33.2 g, 105.9 mmol), H2O2 (10.6 mL), and acetic acid (424 mL) were placed in a round-bottom flask and tested at room temperature in the same manner as Sub-1-d-55 to obtain 31.4 g of the product. (Yield: 90%)

[0191] (3) Synthesis of Sub-1-83

[0192] Sub-1-d-83 (31.4 g, 95.3 mmol) and H2SO4 (94.2 mL) were added and dissolved, and then the same experiment as Sub-1-55 was carried out to obtain 25.0 g of the product. (Yield: 88%)

[0193] 5. Synthesis of Sub-1-97

[0194]

[0195] (1) Synthesis of Sub-1-g-97

[0196] After placing 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), and H2O (251 mL) in a round-bottom flask, the experiment was carried out at 80 °C in the same manner as Sub-1-g-1 above to obtain 34.1 g of the product. (Yield: 70%)

[0197] (2) Synthesis of Sub-1-97

[0198] After dissolving Sub-1-g-97 (34.1 g, 70.3 mmol) 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), and tert-butyl perbenzoate (27.3 g, 140.5 mmol) were added, and the experiment was carried out at 90 °C in the same manner as Sub-1-1 above. 21.1 g of the product was obtained.

[0199] (Yield: 63%)

[0200] 6. Synthesis of Sub-1-114

[0201]

[0202] (1) Synthesis of Sub-1-c-114

[0203] After placing 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) in a round-bottom flask, the experiment was carried out at 80 °C in the same manner as Sub-1-g-1 to obtain 39.4 g of the product. (Yield: 84%)

[0204] (2) Synthesis of Sub-1-d-114

[0205] 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 carried out at room temperature in the same manner as Sub-1-d-55 to obtain 38.1 g of the product. (Yield: 92%)

[0206] (3) Synthesis of Sub-1-d-114

[0207] 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 carried out to obtain 30.2 g of the product. (Yield: 88%)

[0208] 7. Synthesis Example of Sub-1-127

[0209]

[0210] (1) Synthesis of Sub-1-g-127

[0211] After placing 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), and H2O (320 mL) in a round-bottom flask, the experiment was carried out at 80 °C in the same manner as Sub-1-g-1 to obtain 35.7 g of the product. (Yield: 78%)

[0212] (2) Synthesis of Sub-1-127

[0213] After dissolving Sub-1-g-127 (35.7 g, 99.2 mmol) 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), and tert-butyl perbenzoate (38.5 g, 198 mmol) were added, and the test was carried out at 90 °C in the same manner as Sub-1-1 to obtain 14.9 g of the product. (Yield: 42%)

[0214] 8. Synthesis Example of Sub-1-131

[0215]

[0216] (1) Synthesis of Sub-1-c-131

[0217] After placing 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), and H2O (390 mL) in a round-bottom flask, the experiment was carried out at 80 °C in the same manner as Sub-1-g-1 to obtain 40.3 g of the product. (Yield: 82%)

[0218] (2) Synthesis of Sub-1-d-131

[0219] 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 the test was carried out at room temperature in the same manner as Sub-1-d-55 to obtain 38.5 g of the product. (Yield: 91%)

[0220] (3) Synthesis of Sub-1-131

[0221] Add Sub-1-d-131 (38.5 g, 117 mmol) and H2SO4 (116 mL) and dissolve them. Subsequently, conduct the same experiment as Sub-1-55 to obtain 32.4 g of the product. (Yield: 93%)

[0222] 9. Synthesis of Sub-1-132

[0223]

[0224] (1) Synthesis of Sub-1-g-132

[0225] After placing 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), and H2O (180 mL) in a round-bottom flask, conduct the experiment at 80 °C in the same manner as Sub-1-g-1 to obtain 18.7 g of the product. (Yield: 72%)

[0226] (2) Synthesis of Sub-1-132

[0227] After dissolving Sub-1-g-132 (18.7 g, 52.0 mmol) in a round-bottom flask, add Pd(OAc)2 (0.58 g, 2.60 mmol), 3-nitropyridine (0.32 g, 2.60 mmol), C6F6 (78 mL), DMI (52 mL), and tert-butyl peroxybenzoate (20.2 g, 104 mmol), and conduct the test at 90 °C in the same manner as Sub-1-1 to obtain 12.6 g of the product. (Yield: 68%)

[0228] 10. Synthesis example of Sub-1-133

[0229]

[0230] (1) Synthesis of Sub-1-c-133

[0231] After placing 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), and H2O (480 mL) in a round-bottom flask, conduct the experiment at 80 °C in the same manner as Sub-1-g-1 to obtain 48.1 g of the product. (Yield: 80%)

[0232] (2) Synthesis of Sub-1-d-133

[0233] Place Sub-1-c-133 (48.1 g, 154 mmol), H2O2 (43.9 mL), and acetic acid (614 mL) in a round-bottom flask. At room temperature, obtain 44.5 g of the product in the same manner as Sub-1-d-55. (Yield: 88%)

[0234] (3) Synthesis of Sub-1-133

[0235] Add Sub-1-d-133 (44.5 g, 135 mmol) and H2SO4 (134 mL) and dissolve. Subsequently, conduct the same experiment as Sub-1-55 to obtain 36.6 g of the product. (Yield: 91%)

[0236] The compounds belonging to Sub-1 can be the following compounds, but are not limited to this, and the following

[0237] Table 1 shows the field desorption-mass spectrometry (FD-MS) values of the compounds belonging to Sub-1.

[0238]

[0239]

[0240]

[0241]

[0242]

[0243] [Table 1]

[0244]

[0245]

[0246]

[0247]

[0248]

[0249] II. Synthesis of Sub-2

[0250] Synthesize Sub-2 of Scheme 1 through the reaction path of the following Scheme 4, but not limited to this. Hal 6 is I, Br, or Cl.

[0251] <Reaction Scheme 4>

[0252]

[0253] In Reaction Scheme 4, E and F are defined as in Scheme 1.

[0254] 1. Synthesis Example of Sub-2-2

[0255]

[0256] After placing 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), and toluene (888 mL) in a round-bottom flask, the reaction was carried out 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 obtained organic material was recrystallized through a silica gel column to obtain 45.3 g of the product. (Yield 76%)

[0257] 2. Synthesis Example of Sub-2-3

[0258]

[0259] 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), and 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.

[0260] (Yield: 77%)

[0261] 3. Synthesis Example of Sub-2-94

[0262]

[0263] 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), and 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%)

[0264] 4. Synthesis Example of Sub-2-96

[0265]

[0266] 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), and toluene (318 mL) were tested in a round-bottom flask in the same manner as Sub-2-2 to obtain 26.3 g of the product. (Yield: 77%)

[0267] 5. Synthesis Example of Sub-2-114

[0268]

[0269] 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), and toluene (888 mL) were tested in a round-bottom flask in the same manner as Sub-2-2 to obtain 56.4 g of the product. (Yield: 79%)

[0270] 6. Synthesis Example of Sub-2-156

[0271]

[0272] 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), and toluene (440 mL) were tested in a round-bottom flask in the same manner as Sub-2-2 to obtain 22.4 g of the product. (Yield: 72%)

[0273] 7. Synthesis Example of Sub-2-159

[0274]

[0275] 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), and toluene (440 mL) were tested in a round-bottom flask in the same manner as Sub-2-2 to obtain 21.4 g of the product. (Yield: 69%)

[0276] 8. Synthesis Example of Sub-2-162

[0277]

[0278] 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), and toluene (465 mL) were tested in a round-bottom flask in the same manner as Sub-2-2 to obtain 23.4 g of the product. (Yield: 75%)

[0279] The compounds belonging to Sub-2 may be the following compounds, but are not limited thereto, and the following

[0280] Table 2 shows the FD-MS (field desorption - mass spectrometry) values of the compounds belonging to Sub-2.

[0281]

[0282]

[0283]

[0284]

[0285]

[0286]

[0287]

[0288] [Table 2]

[0289]

[0290]

[0291]

[0292] III. Synthesis of the Final Product 1. Synthesis of P-1

[0293]

[0294] (1) Synthesis of Inter-1-1

[0295] After placing 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), and toluene (280 mL) in a round-bottom flask, the reaction was carried out 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%)

[0296] (2) Synthesis of P-1

[0297] After placing 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), and toluene (112 mL) in a round-bottom flask, the experiment was carried out at 80 °C in the same manner as for Inter-1-1 to obtain 10.3 g of the product. (Yield: 71%)

[0298] 2. Synthesis Example of P-2

[0299]

[0300] (1) Synthesis of Inter-1-2

[0301] After placing 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) in a round-bottom flask, 18.2 g of the product was obtained by conducting the experiment at 80 °C in the same manner as Inter-1-1 above. (Yield: 68%)

[0302] (2) Synthesis of P-2

[0303] After placing 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) in a round-bottom flask, 10.5 g of the product was obtained by conducting the experiment at 80 °C in the same manner as Inter-1-1 above. (Yield: 68%)

[0304] 3. Synthesis Example of P-49

[0305]

[0306] (1) Synthesis of Inter-1-49

[0307] After placing 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) in a round-bottom flask, 8.5 g of the product was obtained by conducting the experiment at 80 °C in the same manner as Inter-1-1 above. (Yield: 71%)

[0308] (2) Synthesis of P-49

[0309] After placing Inter-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), and toluene (77 mL) in a round-bottom flask, 10.2 g of the product was obtained in the same manner as Inter-1-1 above by conducting the experiment at 80 °C. (Yield: 72%)

[0310] 4. Synthesis Example of P-55

[0311]

[0312] (1) Synthesis of Inter-1-55

[0313] After placing 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), and toluene (268 mL) in a round-bottom flask, 17.6 g of the product was obtained in the same manner as Inter-1-1 above by conducting the experiment at 80 °C. (Yield: 71%)

[0314] (2) Synthesis of P-55

[0315] After placing 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), and toluene (108 mL) in a round-bottom flask, 11.9 g of the product was obtained in the same manner as Inter-1-1 above by conducting the experiment at 80 °C. (Yield: 72%)

[0316] 5. Synthesis Example of P-83

[0317]

[0318] (1) Synthesis of Inter-1-83

[0319] After placing 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), and toluene (336 mL) 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%)

[0320] (2) Synthesis of P-83

[0321] After placing 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), and toluene (130 mL) 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%)

[0322] 6. Synthesis Example of P-97

[0323]

[0324] (1) Synthesis of Inter-1-97

[0325] After placing 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), and toluene (207 mL) 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%)

[0326] (2) Synthesis of P-2-97

[0327] After placing 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), and toluene (99 mL) 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%)

[0328] (3) Synthesis of P-97

[0329] After placing 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), and toluene (59 mL) 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%)

[0330] 7. Synthesis Example of P-129

[0331]

[0332] (1) Synthesis of Inter-1-129

[0333] After placing 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), and toluene (178 mL) 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%)

[0334] (2) Synthesis of P-129

[0335] 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 in the same manner as Inter-1-1 above by conducting the experiment at 80 °C. (Yield: 70%)

[0336] 8. Synthesis Example of P-133

[0337]

[0338] (1) Synthesis of Inter-1-133

[0339] 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 in the same manner as Inter-1-1 above by conducting the experiment at 80 °C. (Yield: 78%)

[0340] (2) Synthesis of P-133

[0341] 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 in the same manner as Inter-1-1 above by conducting the experiment at 80 °C. (Yield: 73%)

[0342] 9. Synthesis Example of P-134

[0343]

[0344] (1) Synthesis of Inter-1-134

[0345] After placing 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), and toluene (134 mL) 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%)

[0346] (2) Synthesis of P-134

[0347] After placing 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), and toluene (91 mL) 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%)

[0348] 10. Synthesis Example of P-150

[0349]

[0350] After placing 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), and toluene (324 mL) 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%)

[0351] 11. Synthesis Example of P-152

[0352]

[0353] 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 the reaction was carried out at 80 °C for 3 hours to form a deuterated material. Samples were taken regularly and the degree of deuterium was measured 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 carried out using toluene and acetone solvents to obtain 14.1 g (yield: 90%) of the deuterated compound P-152. The final mass was determined by LC-MS to confirm that it was 85.2% deuterated.

[0354] Meanwhile, the FD-MS values of Compounds P-1 to P-152 of the present invention prepared according to the above synthesis examples are shown in Table 3 below.

[0355] [Table 3]

[0356]

[0357]

[0358]

[0359]

[0360] Evaluation of Organic Electronic Component Fabrication

[0361] [Example 1] Red Organic Light-Emitting Device (Luminescence-Assisting Layer)

[0362] The compound of the present invention is used as a light-emitting auxiliary layer material to fabricate an organic electroluminescent device according to a conventional method. First, 4,4',4”-tris[2-naphthyl(phenyl)amino]triphenylamine (abbreviated as 2-TNATA) is vacuum-deposited to a thickness of 60 nm on an ITO layer (anode) formed on a glass substrate to form a hole injection layer. Then, on the hole injection layer, N,N'-bis(1-naphthyl)-N,N'-bis-phenyl-(1,1'-biphenyl)-4,4'-diamine (abbreviated as NPB) is vacuum-deposited as a hole transport compound to a thickness of 60 nm to form a hole transport layer. Then, the compound P-1 of the present invention is vacuum-deposited to a thickness of 40 nm on the hole transport layer to form a light-emitting auxiliary layer. After that, on the light-emitting auxiliary layer, by using 4,4'-N,N'-dicarbazole-biphenyl (abbreviated as CBP) as a host material and bis(1-phenylisoquinolinato)iridium(III) acetylacetonate (hereinafter referred to as (piq)2Ir(acac)) as a dopant doped at a weight ratio of 95:5, it is vacuum-deposited to a thickness of 30 nm on the light-emitting auxiliary layer to form a light-emitting layer. Then, (1,1'-biphenyl-4-yl)bis(2-methyl-8-quinolinolato)aluminum (hereinafter referred to as BAlq) is vacuum-deposited to a thickness of 5 nm on the light-emitting layer to form a hole blocking layer, and bis(10-hydroxybenzo[h]quinolinato)beryllium (hereinafter referred to as BeBq2) is vacuum-deposited on the hole blocking layer to a thickness of 35 nm to form an electron transport layer. Then, alkali metal halide LiF is deposited to a thickness of 0.2 nm on the electron transport layer as an electron injection layer. Then, on the electron injection layer, Al is deposited to a thickness of 150 nm and serves as a cathode to prepare an organic electroluminescent device.

[0363] [Example 2] to [Example 23]

[0364] An organic electroluminescent device is fabricated in the same manner as in Example 1, but the compound of the present invention described in Table 4 is used instead of the compound P-1 of the present invention as the light-emitting auxiliary layer material.

[0365] [Comparative Example 1]

[0366] An organic electroluminescent device is fabricated in the same manner as in Example 1, but the light-emitting auxiliary layer is not formed.

[0367] [Comparative Example 2] to [Comparative Example 6]

[0368] An organic electroluminescent device is fabricated in the same manner as in Example 1, but Comparative Compounds A to E are used instead of the compound P-1 of the present invention as the light-emitting auxiliary layer material.

[0369]

[0370] By applying a forward bias DC voltage to the organic electroluminescent devices prepared in the examples and comparative examples prepared in this manner, the electroluminescence (EL) characteristics were measured using a PR-650 from photo research, and as a measurement result, the service life measurement device manufactured by McScience was used at 2500 cd / m 2 Standard brightness was measured to determine the T95 service life. Table 4 below shows the device manufacturing and evaluation results.

[0371] [Table 4]

[0372]

[0373]

[0374] Referring to Table 4, when the material for the organic electroluminescent device of the present invention is used as the light-emitting auxiliary layer material to manufacture a red organic light-emitting device, compared with the comparative examples in which no light-emitting auxiliary layer is formed or in which comparative compounds A to E are used, the driving voltage, luminous efficiency, and service life of the organic electroluminescent device are significantly improved.

[0375] In other words, in Comparative Examples 2 to 6 using Comparative Compounds A to E as the light-emitting auxiliary layer instead of Comparative Example 1 in which no light-emitting auxiliary layer is formed, the driving voltage, efficiency, and service life of the device are improved. When the compound of the present invention is used as the material for the light-emitting auxiliary layer, compared with when Comparative Compounds A to E are used as the light-emitting auxiliary layer, the driving voltage of the organic electroluminescent device is reduced, and the luminous efficiency and service life are improved.

[0376] Comparing Comparative Compound A or Comparative Compound E with the compound of the present invention, the structure in which dibenzofuran or dibenzothiophene is bonded between amines is the same, but the compound of the present invention has a structure in which dibenzofuran or dibenzothiophene is further substituted by an amino group. Therefore, the refractive index when dibenzofuran or dibenzothiophene is bonded to an amine group is significantly higher than when it is substituted by 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 invention is the same as Comparative Compound B in that an amine group substitutes dibenzofuran or dibenzothiophene, but different in that a linking group between dibenzofuran or dibenzothiophene and the amine group necessarily exists.

[0378] Thus, the compounds of the present invention differ from the comparative compounds by introducing a linking group between dibenzofuran or dibenzothiophene and the amine group, such that the conjugation length becomes longer than that of comparative compound B, thus improving the hole properties, and thus significantly increasing the drive and efficiency compared to the comparative compounds, and increasing the chemical stability of the non-bonding electron pairs, and also increasing the service life.

[0379] Comparative compound C was compared with the compound of the present invention, which has the same structure as the compound of the present invention, but the bonding positions of dibenzothiophene between the amines are the 3-position and the 7-position, and the position of dibenzothiophene bonded to the amine is the 3-position substitution. Figure 6 The HOMO electron clouds of comparative compound C and the compound P-55 of the present invention are shown.

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

[0381] Furthermore, in order to confirm the improvement of the hole mobility, an organic electronic device fabricated with an ITO layer (anode) / 2-TNATA 60 nm / NPB 60 nm / comparative compound C or the compound P-55 of the present invention / HATCN 10 nm / Al (cathode) 150 nm and HOD (hole-only device) was measured, and the results were confirmed by Figure 5 and Table 5 below.

[0382] [Table 5]

[0383]

[0384]

[0385] Reference Figure 5 and Table 5, it can be seen that at a current density of 0.1 mA / cm 2 , the driving voltage of comparative compound C is 2.19 V, while the driving voltage of the compound P-55 of the present invention is 0.61 V, and the difference between comparative compound C and the compound P-55 of the present invention is 1.58 V. Furthermore, at a current density of 10 mA / cm 2 , the driving voltage of comparative compound C is 2.97 V, while the driving voltage of the compound P-55 of the present invention is 1.35 V, and it can be seen that the difference between comparative compound C and the compound P-55 of the present invention is 1.62 V. From this, it can be seen that the compound of the present invention has a more improved hole mobility compared to comparative compound C.

[0386] That is, based on the above points, it can be judged that the compound of the present invention shows superior device characteristics compared with Comparative Compound C.

[0387] Comparative Compound D and the compound of the present invention were compared. Comparative Compound D has a structure in which a fluorene group is introduced between amines, while the compound of the present invention has a structure in which dibenzofuran or dibenzothiophene is bonded between amines. It can be confirmed that the refractive index when 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.

[0388] In summary, although Comparative Compounds A to E and the compound of the present invention are composed of similar components, the introduction of a linking group between 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, and charge balance of holes and electrons, more suitable for the red light-emitting auxiliary layer. Therefore, the device results of Examples 1 to 23 are significantly superior to the device results of Comparative Examples 2 to 6.

[0389] In the case of the light-emitting auxiliary layer, since it is necessary to understand the correlation between the hole transport layer and the light-emitting layer (host), even when using a similar core, it is difficult for those of ordinary skill in the art to infer the characteristics of the light-emitting auxiliary layer using the compound of the present invention.

[0390] In addition, in the evaluation results of the above device manufacturing, the device characteristics in which only the compound of the present invention is applied to the light-emitting auxiliary layer have been described, but the compound of the present invention can be applied to the hole transport layer, or can be applied to both the hole transport layer and the light-emitting auxiliary layer.

[0391] Although the exemplary embodiments of the present invention have been 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 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 to include all technical concepts within the scope equivalent to the claims as belonging to the present invention.

[0393] 100, 200, 300: Organic electronic element 110: First electrode

[0394] 120: Hole injection layer 130: Hole transport layer

[0395] 140: Light-emitting layer 150: Electron transport layer

[0396] 160: Electron injection layer 170: Second electrode

[0397] 180: Light efficiency enhancement layer 210: Buffer layer

[0398] 220: Luminescence assisting layer 320: First hole injection layer

[0399] 330: First hole transport layer 340: First light-emitting layer

[0400] 350: First electron transport layer 360: First charge generation layer

[0401] 361: Second charge generation layer 420: Second hole injection layer

[0402] 430: Second hole transport layer 440: Second light-emitting layer

[0403] 450: Second electron transport layer CGL: Charge generation layer

[0404] ST1: First stack ST2: Second stack

Claims

1. A compound represented by Formula 3-1 or Formula 3-11: Wherein, 1) R 1 , R 2 , R 3 and R 4 are the same as or different from each other and are each independently selected from hydrogen; deuterium; C6-C 25 aryl group; C1-C 24 alkyl group, 2) X and Y are each independently O or S, 3) L 1 and L 2 are the same as or different from each other and are each independently selected from a single bond; C6-C 25 arylene group, 4)L 4 Represented by any one of Formula b-1 to Formula b-10: Formula b-10 Among Formulas b-1 to b-10 a) R 5 、R 6 、R 7 and R 8 each independently is hydrogen; or deuterium, b) e, g, and h are each independently an integer from 0 to 4, and f is an integer from 0 to 6, 5)Ar 1 ,Ar 2 and Ar 3 Each independently is C6-C 25 aryl groups, 6) b, c, and d’ are each independently an integer from 0 to 3, and a is an integer from 0 to 4, 7) Wherein, The aryl group, arylene group, and alkyl group may be substituted with one or more substituents selected from deuterium; C1-C 20 alkyl group; C2-C 20 alkenyl group; C6-C 20 aryl group; C6-C aryl group substituted with deuterium 20 aryl group.

2. The compound according to claim 1, wherein the compound represented by Formula 3-1 is represented by any one of Formulas 6-1 to 6-4: 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, c and d’ are the same as those defined in claim 1.

3. The compound according to claim 1, wherein the compound represented by Formula 3-11 is represented by any one of Formulas 6-17 to 6-20: 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, c and d’ are the same as those defined in claim 1.

4. The compound according to claim 1, wherein the compound represented by Formula 3-1 or Formula 3-11 is represented by any one of the following compounds:

5. 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 contains the single compound represented by Formula 3-1 or Formula 3-11 according to claim 1 or two or more compounds.

6. The organic electronic element according to claim 5, wherein the organic material layer includes 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.

7. The organic electronic element according to claim 5, wherein the organic material layer is a light-emitting auxiliary layer.

8. The organic electronic element according to claim 5, wherein the organic material layer is a hole transport layer.

9. The organic electronic element according to claim 5, further comprising a light efficiency enhancement layer formed on at least one surface of the surfaces of the anode and the cathode that is opposite to the organic material layer.

10. The organic electronic element according to claim 5, wherein the organic material layer is a light efficiency enhancement layer.

11. The organic electronic element according to claim 5, wherein the organic material layer includes at least two or more stacked bodies, and the stacked bodies include a hole transport layer, a light-emitting layer, and an electron transport layer sequentially formed on the anode.

12. The organic electronic element according to claim 11, wherein the organic material layer further includes a charge generation layer formed between the two or more stacked bodies.

13. Electronic device, comprising: A display device including the organic electronic element according to claim 5; And a control unit for driving the display device.

14. The electronic device according to claim 13, wherein the electronic device is any one of an organic electroluminescent device, an organic solar cell, an organic photoreceptor, an organic transistor, and a device for monochromatic or white illumination.

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