Compound for organic electric element, organic electric element using same, and electronic device of same

Abstract

The present invention provides: a compound represented by chemical formula 1; an organic electric element comprising a first electrode, a second electrode, and an organic material layer between the first electrode and the second electrode; and an electronic device comprising the organic electric element. By including the compound of chemical formula 1 in the organic material layer, the driving voltage of the organic electric element can be lowered, and the luminous efficiency and lifespan thereof can be improved.

Description

Compounds for organic electric devices, organic electric devices using the same, and electronic devices thereof

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

[0002] Generally, organic light emitting diodes (OLEDs) are devices that convert electrical energy into light energy using organic materials. Organic electronic devices utilizing the organic light emitting diode (OLED) phenomenon typically have a structure comprising an anode, a cathode, and an organic layer between them. These organic layers are often multilayered, composed of different materials, to enhance the efficiency and stability of the device. For example, these layers may include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer.

[0003] The biggest issues with organic light-emitting diodes are their lifespan and efficiency, and as displays become larger in size, these efficiency and lifespan issues must be resolved.

[0004] Efficiency, lifespan, and operating voltage are interrelated. As efficiency increases, the operating voltage decreases relatively. As the operating voltage decreases, the crystallization of organic substances due to Joule heating generated during operation decreases, which results in a tendency for the lifespan to increase.

[0005] However, simply improving the organic layers cannot maximize efficiency. This is because long life and high efficiency can be achieved simultaneously only when the energy levels and T1 values ​​between each organic layer, as well as the material's inherent properties (mobility, interfacial properties, etc.) are optimally combined.

[0006] Therefore, in order to fully utilize the excellent characteristics of organic electronic devices, it is necessary to develop materials that form the organic layer within the device, especially the light-emitting auxiliary layer.

[0007] The purpose of the present invention is to provide a compound for an organic electric device that can lower the driving voltage of the device and improve the luminous efficiency and lifespan of the device, an organic electric device using the same, and an electronic device thereof.

[0008] In one aspect, the present invention provides a compound represented by the following chemical formula:

[0009]

[0010] In another aspect, the present invention provides an organic electric element and an electronic device thereof comprising a compound represented by the above chemical formula.

[0011] By using the compound according to an embodiment of the present invention as a material for an organic electric device, the driving voltage of the device can be lowered, and the luminous efficiency and lifespan can be improved.

[0012] Figures 1 to 3 are exemplary diagrams of organic light-emitting devices according to embodiments of the present invention.

[0013] [Explanation of symbols]

[0014] 100, 200, 300: Organic electroluminescent element 110: First electrode

[0015] 120: Hole injection layer 130: Hole transport layer

[0016] 140: Emitting layer 150: Electron transport layer

[0017] 160: Electron injection layer 170: Second electrode

[0018] 180: Light efficiency improvement layer 210: Buffer layer

[0019] 220: Light-emitting auxiliary layer 320: First hole injection layer

[0020] 330: First hole transport layer 340: First light-emitting layer

[0021] 350: First electron transport layer 360: First charge generation layer

[0022] 361: Second charge generation layer 420: Second hole injection layer

[0023] 430: Second hole transport layer 440: Second light-emitting layer

[0024] 450: Second electron transport layer CGL: Charge generation layer

[0025] ST1: First stack ST2: Second stack

[0026] The terms "aryl group," "arylene group," and "aromatic ring" as used herein mean a hydrocarbon aromatic ring group, each having 6 to 60 carbon atoms unless otherwise specified, but is not limited thereto. In the present invention, the aryl group or arylene group includes a monocyclic ring, a polycyclic ring, a condensed ring, and the like.

[0027] As used herein, the term "fluorenyl group" means a substituted or unsubstituted fluorenyl group, and "fluorenylene group" means a substituted or unsubstituted fluorenylene group. The fluorenyl group or fluorenylene group used in the present invention includes a spiro compound formed by R and R' bonding to each other in the structure below, and also includes a compound in which adjacent R" bonds to each other to form a ring. The "substituted fluorenyl group" and the "substituted fluorenylene group" mean that at least one of R, R', and R" in the structure below is a substituent other than hydrogen, and the number of R" in the chemical formula below may be 1 to 8. In the present specification, regardless of the valence, a fluorenyl group, a fluorenylene group, etc. may be described as a fluorene group or fluorene.

[0028]

[0029] The term "spiro compound" as used herein has a "spiro linkage," which means a linkage formed by two rings sharing only one atom. The atom shared between the two rings is called a "spiro atom," and depending on the number of spiro atoms contained in a compound, these are called "monospiro-," "dicepiro-," and "trispiro-" compounds, respectively.

[0030] The term "heterocyclic group" used herein includes not only aromatic heterocycles such as "heteroaryl group" or "heteroarylene group" but also non-aromatic heterocycles, and unless otherwise stated means, but is not limited to, a ring having 2 to 60 carbon atoms each containing one or more heteroatoms. The term "heteroatom" used herein, unless otherwise stated, represents an element other than carbon, such as N, O, S, P, or Si, and may include a heteroatom group such as SO2, P=O, etc. instead of carbon forming the ring, as in the following compounds.

[0031]

[0032] In addition, a heterocyclic group includes a monocyclic ring, polycyclic ring, or condensed ring containing a heteroatom, and in the case of a condensed ring, if at least one of the condensed rings is a ring containing a heteroatom, it is defined as a heterocyclic ring. For example, a condensed ring in which a heterocyclic ring such as furan, dihydrofuran, thiophene, pyrrole, pyridine, etc. and an aromatic ring such as benzene, naphthalene, phenanthrene, etc. are condensed, or an aliphatic ring such as cyclopentane, cyclohexane, etc. are condensed is also considered a heterocyclic ring, and a spiro compound in which at least one ring contains a heteroatom is also considered a heterocyclic ring.

[0033] The term "aliphatic ring" used in this specification refers to a cyclic hydrocarbon other than an aromatic hydrocarbon, including a monocyclic ring, a polycyclic ring, a condensed ring, a spiro compound, etc., and unless otherwise stated, refers to a ring having 3 to 60 carbon atoms, but is not limited thereto. In particular, an aliphatic ring (group) in this specification is defined as a hydrocarbon ring that does not contain any aromatic rings. Therefore, not only a saturated hydrocarbon ring such as a cycloalkyl group, but also a ring having one or more double bonds in the ring is considered to be an aliphatic ring as long as it is not an aromatic hydrocarbon.

[0034] The term "fused ring(group)" or "condensed ring(group)" used herein, unless otherwise stated, means a ring in which an aliphatic ring and an aromatic hydrocarbon (aromatic ring group or aryl ring) are condensed with each other, and unless otherwise stated, means a ring in which an aliphatic ring having 3 to 60 carbon atoms and an aromatic hydrocarbon having 6 to 60 carbon atoms are condensed with each other.

[0035] In this specification, the 'group name' corresponding to the aryl group, arylene group, heterocyclic group, etc., which are exemplified as examples of each symbol and its substituent, may be described as the 'group name reflecting the valence', but may also be described as the 'parent compound name'. For example, in the case of 'phenanthrene', which is a type of aryl group, the name of the group may be described by distinguishing the valence, such as 'phenanthryl' for the monovalent 'group' and 'phenantrylene' for the divalent group, but it may also be described as the parent compound name 'phenanthrene' regardless of the valence. Similarly, in the case of pyrimidine, it may be described as 'pyrimidine' regardless of the valence, or it may be described as the 'group name' of the corresponding valence, such as pyrimidinyl group for monovalent and pyrimidinylene for divalent.

[0036] In addition, in this specification, numbers or alphabets indicating positions may be omitted when describing compound names or substituent names. For example, pyrido[4,3-d]pyrimidine may be described as pyridopyrimidine, benzofuro[2,3-d]pyrimidine as benzofuropyrimidine, 9,9-dimethyl-9H-fluorene as dimethylfluorene, etc. Accordingly, both benzo[g]quinoxaline and benzo[f]quinoxaline may be described as benzoquinoxaline.

[0037] Additionally, unless explicitly stated otherwise, the chemical formulas used in the present invention are applied in the same manner as the substituent definitions by the index definitions of the chemical formulas below.

[0038]

[0039] Here, if a is an integer of 0, the substituent R 1means that it is absent, that is, when a is 0, it means that all the carbons forming the benzene ring are bonded with hydrogen, and in this case, the indication of hydrogen bonded to carbon can be omitted and the chemical formula or compound can be described. In addition, when a is an integer of 1, one substituent R 1 It binds to one of the carbons forming the benzene ring, and when a is an integer of 2 or 3, it can bind as follows, for example, and when a is an integer of 4 to 6, it binds to the carbon of the benzene ring in a similar manner, and when a is an integer of 2 or more, R 1 may be the same or different.

[0040]

[0041] In addition, unless otherwise stated herein, a ring refers to an aryl ring, a heteroaryl ring, a fluorene ring, an aliphatic ring, a fused ring, etc., and a number-ring refers to a condensed ring, and a number-atom ring refers to a ring shape. For example, naphthalene corresponds to a two-ring condensed ring, anthracene corresponds to a three-ring condensed ring, thiophene and furan correspond to a five-membered heterocycle, and benzene and pyridine correspond to a six-membered aromatic ring.

[0042] In addition, unless otherwise stated in this specification, the rings formed by bonding adjacent groups to each other are C6~C 60 Aromatic ring group; Fluorenyl group; C2~C containing at least one heteroatom among O, N, S, Si and P 60 Heterocyclic group of; C3~C 60 Aliphatic ring group; and C3~C 60 Aliphatic ring and C6~C 60 The aromatic ring may be selected from the group consisting of a fused ring group. Here, the aromatic ring group may be an aryl ring, and the heterocyclic group may include a heteroaryl ring.

[0043] Unless otherwise stated herein, 'neighboring groups' includes, for example, R1 and R2, R2 and R3, R3 and R4, R5 and R6, as well as R7 and R8 sharing a carbon, and may also include substituents bonded to non-adjacent ring elements (carbon, nitrogen, etc.), such as R1 and R7, R1 and R8, or R4 and R5. That is, when there is a substituent on a ring element such as a carbon or nitrogen that is immediately adjacent, they can be neighboring groups, but when no substituent is bonded to the ring element at the immediately adjacent position, the substituent bonded to the next ring element can be a neighboring group, and substituents bonded to the same ring carbon can also be neighboring groups. In the following chemical formula, when substituents bonded to the same carbon, such as R7 and R8, bond to each other to form a ring, a compound including a spiro moiety can be formed.

[0044] ,

[0045] Additionally, in this specification, the expression 'adjacent groups can combine with each other to form a ring' is used with the same meaning as 'adjacent groups combine with each other to selectively form a ring', and means a case where at least one pair of adjacent groups combine with each other to form a ring.

[0046] In addition, unless otherwise stated herein, substituents such as aryl group, arylene group, fluorenyl group, fluorenylene group, heterocyclic group, aliphatic ring group, fused ring group, alkyl group, alkenyl group, alkynyl group, alkoxy group, aryloxy group, alkylthio group, arylthio group, etc., rings formed by bonding adjacent groups to each other, etc., are each deuterium; halogen; cyano group; nitro group; siloxane group; C6-C 30Aryl group of; Fluorenyl group; C2-C containing at least one heteroatom selected from the group consisting of O, N, S, Si and P 30 Heterocyclic group of; C3-C 30 Aliphatic ring group; C3~C 60 Aliphatic ring and C6~C 60 Fused ring group of aromatic ring; C1-C 20 alkyl group of; C2-C 20 alkenyl group of; C2-C 20 Alkynyl group of; C1-C 20 Alkoxy group of; C6-C 20 Aryloxy group of; C1-C 20 Alkylthio group of; C6-C 20 Arylthio group of; C1-C 20 Alkyl group or C6-C 20 A silane group substituted or unsubstituted with an aryl group; and C1-C 20 Alkyl group or C6-C 20 It may be substituted with one or more substituents selected from the group consisting of phosphine oxide groups substituted or unsubstituted with an aryl group.

[0047] Unless otherwise stated in this specification, the symbols "*" or " " represents the joining part.

[0048] Hereinafter, the laminated structure of an organic electric device including the compound of the present invention will be described with reference to FIGS. 1 to 3.

[0049] When assigning reference numerals to components in each drawing, it should be noted that identical components are assigned the same numerals whenever possible, even if they appear on different drawings. Furthermore, when describing the present invention, if a detailed description of a related known configuration or function is deemed likely to obscure the gist of the present invention, such detailed description will be omitted.

[0050] When describing components of the present invention, terms such as first, second, A, B, (a), (b), etc. may be used. These terms are only intended to distinguish the components from other components, and the nature, order, or sequence of the components are not limited by the terms. When it is described that a component is "connected," "coupled," or "connected" to another component, it should be understood that the component may be directly connected or connected to the other component, but another component may also be "connected," "coupled," or "connected" between each component.

[0051] Furthermore, when a component such as a layer, membrane, region, or plate is said to be "on" or "over" another component, it should be understood that this includes not only the case where it is "directly on" the other component, but also the case where there are other components in between. Conversely, when a component is said to be "directly on" another part, it should be understood that there are no other components in between.

[0052] Figures 1 to 3 are exemplary diagrams of organic electric devices according to embodiments of the present invention.

[0053] Referring to FIG. 1, an organic electric element (100) according to one embodiment of the present invention includes a first electrode (110), a second electrode (170), and an organic layer formed between the first electrode (110) and the second electrode (170) formed on a substrate (not shown), and an inorganic layer may be included between the first electrode (110) and the second electrode (120).

[0054] For example, the first electrode (110) may be an anode, the second electrode (170) may be a cathode, and in the case of an inverted type, the first electrode may be a cathode and the second electrode may be an anode.

[0055] The above organic layer refers to a layer containing at least one organic material. For example, the organic layer may include a hole injection layer (120), a hole transport layer (130), a light-emitting layer (140), an electron transport layer (150), and an electron injection layer (160). However, the electron injection layer (160) may be an inorganic layer that does not contain an organic material.

[0056] Specifically, 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) can be sequentially formed on a first electrode (110).

[0057] Preferably, a light efficiency improvement layer (180) may be formed on one side of the first electrode (110) or the second electrode (170) that is not in contact with the organic layer or the inorganic layer, and when the light efficiency improvement layer (180) is formed, the light efficiency of the organic electric element may be improved.

[0058] For example, a light efficiency improvement layer (180) can be formed on the second electrode (170). In the case of a top emission organic light emitting device, the formation of the light efficiency improvement layer (180) can reduce optical energy loss due to SPPs (surface plasmon polaritons) in the second electrode (170), and in the case of a bottom emission organic light emitting device, the light efficiency improvement layer (180) can serve as a buffer for the second electrode (170).

[0059] A buffer layer (210) or a light-emitting auxiliary layer (220) may be further formed between the hole transport layer (130) and the light-emitting layer (140), which will be described with reference to FIG. 2.

[0060] Referring to FIG. 2, an organic electric element (200) according to another embodiment of the present invention may include a hole injection layer (120), a hole transport layer (130), a buffer layer (210), a light-emitting auxiliary layer (220), a light-emitting layer (140), an electron transport layer (150), an electron injection layer (160), and a second electrode (170) sequentially formed on a first electrode (110), and a light efficiency improvement layer (180) may be formed on the second electrode.

[0061] Although not shown in FIG. 2, an electron transport auxiliary layer may be further formed between the light-emitting layer (140) and the electron transport layer (150).

[0062] Additionally, according to another embodiment of the present invention, the organic layer may be formed in a form in which a plurality of stacks including a hole transport layer, a light-emitting layer, and an electron transport layer are formed. This will be described with reference to FIG. 3.

[0063] Referring to FIG. 3, an organic electric element (300) according to another embodiment of the present invention may have two or more sets of stacks (ST1, ST2) of organic layers formed of multiple layers formed between a first electrode (110) and a second electrode (170), and a charge generation layer (CGL) may be formed between the stacks of organic layers.

[0064] Specifically, an organic electric device according to one embodiment of the present invention may include a first electrode (110), a first stack (ST1), a charge generation layer (CGL: Charge Generation Layer), a second stack (ST2), a second electrode (170), and a light efficiency improvement layer (180).

[0065] The first stack (ST1) is an organic layer formed on the first electrode (110), which may include a first hole injection layer (320), a first hole transport layer (330), a first light-emitting layer (340), and a first electron transport layer (350), and the second stack (ST2) may include a second hole injection layer (420), a second hole transport layer (430), a second light-emitting layer (440), and a second electron transport layer (450). In this way, the first stack and the second stack may be organic layers having the same stacked structure, but may also be organic layers having different stacked structures.

[0066] A charge generation layer (CGL) may be formed between the first stack (ST1) and the second stack (ST2). The charge generation layer (CGL) may include a first charge generation layer (360) and a second charge generation layer (361). This charge generation layer (CGL) is formed between the first light-emitting layer (340) and the second light-emitting layer (440) to increase the current efficiency generated in each light-emitting layer and to smoothly distribute charges.

[0067] The first light-emitting layer (340) may include a light-emitting material including a blue fluorescent dopant in a blue host, and the second light-emitting layer (440) may include a material doped with a greenish yellow dopant and a red dopant in a green host, but the materials of the first light-emitting layer (340) and the second light-emitting layer (440) according to the embodiment of the present invention are not limited thereto.

[0068] In FIG. 3, n can be an integer from 1 to 5, and when n is 2, a charge generation layer (CGL) and a third stack can be additionally stacked on the second stack (ST2).

[0069] When a plurality of light-emitting layers are formed by a multi-layer stack structure as shown in Fig. 3, not only can an organic light-emitting device that emits white light be manufactured by the mixing effect of the light emitted from each light-emitting layer, but an organic light-emitting device that emits light of various colors can also be manufactured.

[0070] The compound represented by the chemical formula 1 of the present invention may be included in an organic layer. For example, the compound represented by the chemical formula 1 of the present invention may be used as a material for a hole injection layer (120, 320, 420), a hole transport layer (130, 330, 430), a buffer layer (210), a light-emitting auxiliary layer (220), an electron transport layer (150, 350, 450), a light-emitting layer (140, 340, 440), or a light efficiency improvement layer (180), but may preferably be used as a material for a light-emitting auxiliary layer (220).

[0071] Even if the core is identical or similar, the band gap, electrical properties, and interface properties can vary depending on which substituent is bonded at which position. Therefore, research on the selection of the core and the combination of sub-substituents bonded to it is necessary. In particular, when the energy level and T1 value between each organic layer and the intrinsic properties of the material (mobility, interface properties, etc.) are optimally combined, long life and high efficiency can be achieved simultaneously.

[0072] Therefore, in the present invention, by using the compound represented by chemical formula 1 as a material of the light-emitting auxiliary layer (220), the energy level and T1 value between each organic layer, and the inherent characteristics of the material (mobility, interface characteristics, etc.) can be optimized, thereby simultaneously improving the lifespan and efficiency of the organic electric device.

[0073] An organic light emitting diode according to an embodiment of the present invention may be manufactured using various deposition methods. It may be manufactured using a deposition method such as PVD or CVD. For example, it may be manufactured by forming an anode (110) by depositing a metal or a conductive metal oxide or an alloy thereof on a substrate, forming an organic 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, and then depositing a material that can be used as a cathode (170) thereon. In addition, an emission auxiliary layer (220) may be further formed between the hole transport layer (130) and the light emitting layer (140), and an electron transport auxiliary layer (not shown) may be further formed between the emission layer (140) and the electron transport layer (150), or may be formed in a stack structure as described above.

[0074] In addition, the organic layer can be manufactured with a smaller number of layers by using various polymer materials and a solution process or solvent process other than a deposition method, such as a spin coating process, a nozzle printing process, an inkjet printing process, a slot coating process, a dip coating process, a roll-to-roll process, a doctor blading process, a screen printing process, or a thermal transfer method. Since the organic layer according to the present invention can be formed by various methods, the scope of the present invention is not limited by the formation method.

[0075] An organic electric device according to one embodiment of the present invention may be a front-emitting, back-emitting, or double-sided emitting type depending on the material used.

[0076] In addition, the organic electric device according to one embodiment of the present invention may be selected from the group consisting of an organic light-emitting device, an organic solar cell, an organic photoconductor, an organic transistor, a device for monochrome lighting, and a device for quantum dot display.

[0077] Another embodiment of the present invention may include a display device including the organic electric element of the present invention described above, and an electronic device including a control unit for controlling the display device. In this case, the electronic device may be a current or future wired or wireless communication terminal, and includes all electronic devices such as mobile communication terminals such as cell phones, navigation systems, game consoles, various TVs, and various computers.

[0078] Hereinafter, a compound according to one aspect of the present invention will be described.

[0079] A compound according to one aspect of the present invention is represented by the following chemical formula 1.

[0080] <Chemical Formula 1> <Chemical Formula A>

[0081]

[0082] In the above chemical formula 1, each symbol can be defined as follows.

[0083] A is chemical formula A.

[0084] X 1 and X 2 are O or S respectively.

[0085] Ar 1 and Ar 2 are independently C6~C 60 It is an aryl group. At this time, the aryl group does not include a fluorenyl group.

[0086] Ar 3 Silver C6~C 60 Aryl group of; C3~C 60 Aliphatic ring group of; and C1~C 20 is selected from the group consisting of alkyl groups.

[0087] R 1 Inland R 5 are independently hydrogen; deuterium; halogen; cyano group; silane group; C6~C 60 Aryl group of; fluorenyl group; C2~C containing at least one heteroatom among O, N, S, Si and P 60Heterocyclic group of; C3~C 60 Aliphatic ring group; C6~C 60 Aromatic ring and C3~C 60 Fused ring group of aliphatic ring; C1~C 20 Alkyl group of; C2~C 20 Alkenyl group of; C2~C 20 Alkynyl group of; C1~C 20 Alkoxy group of; and C6~C 60 is selected from the group consisting of aryloxy groups, and adjacent groups can be combined with each other to form a ring, provided that adjacent R 5 Except when they combine with each other to form a ring.

[0088] a and e are integers from 0 to 4, b, c and d are integers from 0 to 3, and if they are integers greater than or equal to 2, multiple R 1 Each or multiple R 5 Each is either the same or different from the other.

[0089] Neighboring units, for example, neighboring R 1 Kiri, neighboring R 2 Kiri, neighboring R 3 Kiri, neighboring R 4 When they combine with each other to form a ring, the ring is C6~C 60 Aromatic ring group; Fluorenyl group; C3~C 60 Aliphatic ring group; C2~C containing at least one heteroatom among O, N, S, Si and P 60 Heterocyclic group of; and C3~C 60 Aliphatic ring and C6~C 60 It can be selected from the group consisting of fused ring groups of aromatic rings.

[0090] When adjacent groups combine with each other to form an aromatic ring, the aromatic ring is, for example, C6~C 20 , C6~C 18 , C6~C 16 , C6~C 14 , C6~C 13 , C6~C12 , C6~C 10 , C6, C 10 , C 12 , C 14 , C 15 , C 16 , C 18 It may be an aromatic ring, such as benzene, naphthalene, anthracene, phenanthrene, pyrene, etc.

[0091] Ar 1 Inland Ar 3 , R 1 Inland R 5 If at least one of them is an aryl group, the aryl group is, for example, C6~C 30 , C6~C 29 , C6~C 28 , C6~C 27 , C6~C 26 , C6~C 25 , C6~C 24 , C6~C 23 , C6~C 22 , C6~C 21 , C6~C 20 , C6~C 19 , C6~C 18 , C6~C 17 , C6~C 16 , C6~C 15 , C6~C 14 , C6~C 13 , C6~C 12 , C6~C 11 , C6~C 10 , C6, C 10 , C 12 , C 13 , C 14 , C 15 , C 16 , C 17 , C 18 It may be an aryl group such as, for example, phenyl, biphenyl, naphthyl, terphenyl, phenanthrene, benzophenanthrene, triphenylene, chrysene, etc.

[0092] Ar 3 , R 1 Inland R 5If at least one of them is an aliphatic ring group, the aliphatic ring group is, for example, C3~C 30 , C3~C 29 , C3~C 28 , C3~C 27 , C3~C 26 , C3~C 25 , C3~C 24 , C3~C 23 , C3~C 22 , C3~C 21 , C3~C 20 , C3~C 19 , C3~C 18 , C3~C 17 , C3~C 16 , C3~C 15 , C3~C 14 , C3~C 13 , C3~C 12 , C3~C 11 , C3~C 10 , C3~C8, C3~C6, C6, C 10 , C 11 , C 12 , C 13 , C 14 , C 15 , C 16 , C 17 , C 18 It may be an aliphatic ring group such as cyclobutane, cyclopentane, cyclohexane, bicycloheptane, adamantyl, etc.

[0093] Ar 3 , R 1 Inland R 5 If at least one of them is an alkyl group, the alkyl group is, for example, C1~C 20 , C1~C 10 , C1~C4, C1, C2, C3, C4, etc., and may be, for example, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a t-butyl group, etc.

[0094] The above Ar 1 Inland Ar 3 are respectively deuterium; C1-C 20 alkyl group of; C6-C30 Aryl group of; and C6-C substituted with deuterium 30 It may be substituted with one or more substituents selected from the group consisting of aryl groups.

[0095] The above Ar 1 Inland Ar 3 The aryl group of does not contain a fluorenyl group.

[0096] The above R 1 Inland R 5 are respectively deuterium; halogen; C1-C 20 Alkyl group or C6-C 20 Silane group substituted or unsubstituted with an aryl group; C1-C 20 Alkyl group or C6-C 20 Phosphine oxide substituted or unsubstituted with an aryl group; cyano group; C1-C 20 Alkoxy group of; C6-C 30 Aryloxy group of; C1-C 20 alkyl group of; C2-C 20 alkenyl group of; C2-C 20 Alkynyl group of; C6-C 30 Aryl group of; C6-C substituted with deuterium 30 Aryl group of; fluorenyl group; C3-C 30 Aliphatic ring group; C6-C 30 Aromatic ring and C3-C 30 A fused ring group of an aliphatic ring; and C2-C containing at least one heteroatom among O, N, S, Si and P. 30 It may be substituted with one or more substituents selected from the group consisting of heterocyclic groups, and adjacent substituents may be combined with each other to form a ring, and hydrogen of the substituents may be replaced with deuterium.

[0097] Ar 1 Inland Ar 3 , R 1 Inland R 5 When at least one of them is substituted with an aryl group, the aryl group is, for example, C6~C 30 , C6~C 29 , C6~C28 , C6~C 27 , C6~C 26 , C6~C 25 , C6~C 24 , C6~C 23 , C6~C 22 , C6~C 21 , C6~C 20 , C6~C 19 , C6~C 18 , C6~C 17 , C6~C 16 , C6~C 15 , C6~C 14 , C6~C 13 , C6~C 12 , C6~C 11 , C6~C 10 , C6, C 10 , C 12 , C 13 , C 14 , C 15 , C 16 , C 17 , C 18 It can be an aryl group such as .

[0098] Ar 1 Inland Ar 3 , R 1 Inland R 5 When at least one of them is substituted with an alkyl group, the alkyl group is, for example, C1~C 20 , C1~C 10 , C1~C4, C1, C2, C3, C4, etc., and may be, for example, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a t-butyl group, etc.

[0099] The above chemical formula 1 can be represented by one of the following chemical formulas 1-1 to 1-4.

[0100] <Chemical Formula 1-1> <Chemical Formula 1-2>

[0101]

[0102] <Chemical Formula 1-3> <Chemical Formula 1-4>

[0103]

[0104] In the above chemical formulas 1-1 to 1-4, A, X 1 , Ar 1 , Ar 2 , R 1 , R 2 , R 5 , a, b, and e are as defined in chemical formula 1.

[0105] The above chemical formula A may be one of the following chemical formulas A-1 to A-4.

[0106] <Chemical Formula A-1> <Chemical Formula A-2>

[0107]

[0108] <Chemical Formula A-3> <Chemical Formula A-4>

[0109]

[0110] In the above chemical formulas A-1 to A-4, X 2 , Ar 3 , R 3 , R 4 , c, d are as defined in chemical formula 1.

[0111] Ar 1 Inland Ar 3 At least one of the compounds may be selected from the group consisting of the following chemical formulae Ar-1 to Ar-4, but is not limited thereto.

[0112] <Chemical Formula Ar-1> <Chemical Formula Ar-2> <Chemical Formula Ar-3> <Chemical Formula Ar-4>

[0113]

[0114] In the above chemical formulas Ar-1 to Ar-4, R 6 Inland R 9 are independently hydrogen; deuterium; C1-C 20 alkyl group of; C6-C 30 Aryl group of; and C6-C substituted with deuterium 30It is selected from the group consisting of aryl groups, and adjacent groups are bonded to each other and C6-C 30 , f and h are each an integer from 0 to 5, g is an integer from 0 to 4, and i is an integer from 0 to 7.

[0115] The above chemical formula Ar-2 can be represented by one of the following chemical formulas Ar-2-1 to Ar-2-3.

[0116] <Chemical formula Ar-2-1> <Chemical formula Ar-2-2> <Chemical formula Ar-2-3>

[0117]

[0118] In the above chemical formulas Ar-2-1 to Ar-2-3, R 7 , R 8 , g, h are as defined in the above chemical formula Ar-2.

[0119] Specifically, the compound represented by the above chemical formula 1 may be one of the following compounds, but is not limited thereto.

[0120]

[0121]

[0122]

[0123]

[0124]

[0125]

[0126]

[0127]

[0128]

[0129]

[0130]

[0131]

[0132]

[0133]

[0134]

[0135]

[0136]

[0137]

[0138]

[0139]

[0140]

[0141]

[0142]

[0143]

[0144]

[0145]

[0146]

[0147]

[0148]

[0149]

[0150] .

[0151] In another aspect, the present invention provides an organic electric device comprising a first electrode, a second electrode, and an organic layer between the first electrode and the second electrode, wherein the organic layer comprises a compound of formula 1, and preferably, the compound is included in a light-emitting auxiliary layer.

[0152] In another aspect, the present invention provides an electronic device including a display device including an organic electric element and a control unit for driving the display device, wherein the organic electric element includes a compound represented by the chemical formula 1.

[0153] In another aspect, the present invention provides a compound represented by the chemical formula 1 obtained by recovering and purifying the material of an organic layer from a deposition device after depositing the organic layer in a manufacturing process of an organic electric device. The purity of the compound obtained by recovery and purification is 99.9% or higher.

[0154] In another aspect, the present invention provides a method for recovering a compound, comprising the steps of depositing an organic layer material including a compound represented by Chemical Formula 1, recovering the organic layer material attached to a deposition device, and purifying the recovered organic layer material to obtain a compound represented by Chemical Formula 1 having a purity of 99.9% or higher.

[0155] The above purification step may include a step of recrystallizing the recovered organic layer material using a recrystallization solvent, a step of adsorption separation using an adsorbent, and a step of sublimation purification.

[0156] The above recrystallization step may include a preliminary purification process for obtaining a compound represented by the above chemical formula 1 with a purity of 98% using a recrystallization solvent.

[0157] A polar solvent having a polarity index (PI) of 5.5 to 7.2 is preferably used as the recrystallization solvent, or a mixture of a polar solvent having a polarity index of 5.5 to 7.2 and a non-polar solvent having a polarity index of 2.0 to 4.7 may be used.

[0158] When using a mixture of a polar solvent and a non-polar solvent as a recrystallization solvent, the non-polar solvent may be used in a ratio of 15% (v / v) or less compared to the polar solvent.

[0159] In addition, as a recrystallization solvent, a single solvent of methylpyrrolidone (N-methylpyrrolidone: NMP) is preferably used; or a mixed polar solvent in which any one selected from the group consisting of methylpyrrolidone, dimethyl imidazolidinone (1,3-dimethyl-2-imidazolidinone), 2-pyrrolidone, dimethylformamide (N,N-dimethyl formamide), dimethyl acetamide, and dimethyl sulfoxide is mixed; or a single or mixed nonpolar solvent selected from the group consisting of toluene, dichloromethane (DCM), dichloroethane (DCE), tetrahydrofuran (THF), chloroform, ethyl acetate, and butanone, or a mixture of polar solvents and nonpolar solvents can be used.

[0160] The above preliminary purification process may include a step of dissolving the unrefined organic light-emitting material recovered from the deposition equipment in a polar solvent at 90°C to 120°C and then cooling it to 0°C to 5°C to precipitate crystals.

[0161] The above preliminary purification process may include a step of dissolving an unrefined organic light-emitting material recovered from a deposition device in a polar solvent at 90°C to 120°C, cooling to 35°C to 40°C, adding a non-polar solvent, and then cooling to 0°C to 5°C to precipitate a crystal.

[0162] The above preliminary purification process may include a step of dissolving the crude organic light-emitting material recovered from the deposition equipment in a non-polar solvent, concentrating the solvent, and precipitating crystals while removing the non-polar solvent.

[0163] The above preliminary purification process may include a step of first recrystallizing with a polar solvent and then recrystallizing again with a non-polar solvent.

[0164] In the adsorption separation step using the above adsorbent, activated carbon, silica gel, alumina or a known material for adsorption purposes can be used as the adsorbent.

[0165] Hereinafter, examples of synthesis of a compound represented by Chemical Formula 1 according to the present invention and examples of manufacturing an organic electric device will be described in detail by way of examples, but the present invention is not limited thereto.

[0166] [Synthesis method]

[0167] The compound represented by chemical formula 1 according to the present invention (final product) can be prepared by reacting Sub1 and Sub2 as in the following reaction scheme 1, but is not limited thereto.

[0168] <Reaction Scheme 1> (Hal 1 is Cl, Br or I)

[0169]

[0170] Example compounds of Sub1

[0171] Compounds belonging to Sub 1 may include, but are not limited to, the compounds below, and the FD-MS (Field Desorption-Mass Spectrometry) values ​​of the compounds below are as shown in Table 1.

[0172]

[0173]

[0174]

[0175]

[0176]

[0177]

[0178]

[0179]

[0180]

[0181]

[0182]

[0183] Compound FD-MS Compound FD-MS Sub1-1 m / z = 369.09 (C 24 H 16 ClNO = 369.85) Sub1-2 m / z = 425.15 (C 28 H 24 ClNO = 425.96) Sub1-3 m / z = 369.09 (C 24 H 16 ClNO = 369.85) Sub1-4 m / z = 369.09 (C 24 H 16 ClNO = 369.85) Sub1-5 m / z = 373.12 (C 24 H 12 D4ClNO = 373.87) Sub1-6 m / z = 445.12 (C 30 H 20 ClNO = 445.95) Sub1-7 m / z = 445.12 (C 30 H 20 ClNO = 445.95) Sub1-8 m / z = 369.09 (C 24 H 16 ClNO = 369.85) Sub1-9 m / z = 378.15 (C 24 H7D9ClNO = 378.90) Sub1-10 m / z = 385.19 (C 24 D 16 ClNO = 385.95) Sub1-11 m / z = 445.12 (C 30 H 20 ClNO = 445.95) Sub1-12 m / z = 450.15 (C 30 H 15 D5ClNO = 450.98) Sub1-13 m / z = 425.15 (C 28 H 24 ClNO = 425.96) Sub1-14 m / z = 445.12 (C 30 H 20 ClNO = 445.95) Sub1-15 m / z = 527.20 (C 36 H 30 ClNO = 528.09) Sub1-16 m / z = 419.11 (C 28 H18 ClNO=419.91)Sub1-17m / z=419.11(C 28 H 18 ClNO=419.91)Sub1-18m / z=419.11(C 28 H 18 ClNO=419.91)Sub1-19m / z=385.07(C 24 H 16 ClNS=385.91)Sub1-20m / z=461.1(C 30 H 20 ClNS=462.01)Sub1-21m / z=435.08(C 28 H 18 ClNS=435.97)Sub1-22m / z=435.08(C 28 H 18 ClNS=435.97)Sub1-23m / z=385.07(C 24 H 16 ClNS=385.91)Sub1-24m / z=461.10(C 30 H 20 ClNS=462.01)Sub1-25m / z=435.08(C 28 H 18 ClNS=435.97)Sub1-26m / z=435.08(C 28 H 18 ClNS=435.97)Sub1-27m / z=461.10(C 30 H 20 ClNS=462.01)Sub1-28m / z=385.07(C 24 H 16 ClNS=385.91)Sub1-29m / z=385.07(C 24 H 16 ClNS=385.91)Sub1-30m / z=521.15(C 36 H 24 ClNO=522.04)Sub1-31m / z=501.19(C 34 H 28 ClNO=502.05)Sub1-32m / z=461.10(C 30 H 20 ClNS=462.01)Sub1-33m / z=511.12(C 34 H 22ClNS=512.07)Sub1-34m / z=445.12(C 30 H 20 ClNO=445.95)Sub1-35m / z=399.08(C 25 H 18 ClNS=399.94)Sub1-36m / z=543.18(C 36 H 30 ClNS=544.15)Sub1-37m / z=461.10(C 30 H 20 ClNS=462.01)Sub1-38m / z=461.10(C 30 H 20 ClNS=462.01)Sub1-39m / z=445.12(C 30 H 20 ClNO=445.95)Sub1-40m / z=383.11(C 25 H 18 ClNO=383.88)Sub1-41m / z=521.15(C 36 H 24 ClNO=522.04)Sub1-42m / z=445.12(C 30 H 20 ClNO=445.95)Sub1-43m / z=445.12(C 30 H 20 ClNO=445.95)Sub1-44m / z=445.12(C 30 H 20 ClNO=445.95)Sub1-45m / z=445.12(C 30 H 20 ClNO=445.95)Sub1-46m / z=445.12(C 30 H 20 ClNO=445.95)Sub1-47m / z=495.14(C 34 H 22 ClNO=496.01)Sub1-48m / z=511.12(C 34 H 22 ClNS=512.07)Sub1-49m / z=511.12(C 34 H 22 ClNS=512.07)Sub1-50m / z=571.17(C 40 H 26ClNO=572.10)Sub1-51m / z=527.20(C 36 H 30 ClNO=528.09)Sub1-52m / z=445.12(C 30 H 20 ClNO = 445.95)

[0184] Example compounds of Sub2

[0185] Compounds belonging to Sub 2 may include, but are not limited to, the compounds below, and the FD-MS (Field Desorption-Mass Spectrometry) values ​​of the compounds below are as shown in Table 2.

[0186]

[0187]

[0188]

[0189]

[0190]

[0191]

[0192]

[0193]

[0194]

[0195]

[0196]

[0197]

[0198]

[0199]

[0200]

[0201] Compound FD-MS Compound FD-MS Sub2-1 m / z = 335.13 (C 24 H 17NO=335.41)Sub2-2m / z=345.19(C 24 H7D 10 NO=345.47)Sub2-3m / z=346.2(C 24 H6D 11 NO=346.47)Sub2-4m / z=351.23(C 24 HD 16 NO=351.50)Sub2-5m / z=411.16(C 30 H 21 NO=411.5)Sub2-6m / z=416.19(C 30 H 16 D5NO=416.53)Sub2-7m / z=461.18(C 34 H 23 NO=461.56)Sub2-8m / z=391.19(C 28 H 25 NO=391.51)Sub2-9m / z=385.15(C 28 H 19 NO=385.47)Sub2-10m / z=385.15(C 28 H 19 NO=385.47)Sub2-11m / z=461.18(C 34 H 23 NO=461.56)Sub2-12m / z=411.16(C 30 H 21 NO=411.50)Sub2-13m / z=487.19(C 36 H 25 NO=487.60)Sub2-14m / z=385.15(C 28 H 19 NO=385.47)Sub2-15m / z=315.16(C 22 H 21 NO=315.42)Sub2-16m / z=341.18(C 24 H 23 NO=341.45)Sub2-17m / z=351.11(C 24 H 17 NS=351.47)Sub2-18m / z=427.14(C 30 H 21 NS=427.57)Sub2-19m / z=427.14(C 30 H21 NS=427.57)Sub2-20m / z=451.14(C 32 H 21 NS=451.59)Sub2-21m / z=463.23(C 32 H 33 NS=463.68)Sub2-22m / z=401.12(C 28 H 19 NS=401.53)Sub2-23m / z=331.14(C 22 H 21 NS=331.48)Sub2-24m / z=369.16(C 25 H 23 NS=369.53)Sub2-25m / z=409.19(C 28 H 27 NS=409.59)Sub2-26m / z=335.13(C 24 H 17 NO=335.41)Sub2-27m / z=411.16(C 30 H 21 NO=411.50)Sub2-28m / z=411.16(C 30 H 21 NO=411.50)Sub2-29m / z=427.14(C 30 H 21 NS=427.57)Sub2-30m / z=411.16(C 30 H 21 NO=411.50)Sub2-31m / z=385.15(C 28 H 19 NO=385.47)Sub2-32m / z=461.18(C 34 H 23 NO=461.56)Sub2-33m / z=401.12(C 28 H 19 NS=401.53)Sub2-34m / z=427.14(C 30 H 21 NS=427.57)Sub2-35m / z=427.14(C 30 H 21 NS=427.57)Sub2-36m / z=351.11(C 24 H 17 NS=351.47)Sub2-37m / z=369.16(C25 H 23 NS=369.53)Sub2-38m / z=341.18(C 24 H 23 NO=341.45)Sub2-39m / z=315.16(C 22 H 21 NO=315.42)Sub2-40m / z=409.19(C 28 H 27 NS=409.59)Sub2-41m / z=351.11(C 24 H 17 NS=351.47)Sub2-42m / z=427.14(C 30 H 21 NS=427.57)Sub2-43m / z=331.14(C 22 H 21 NS=331.48)Sub2-44m / z=477.16(C 34 H 23 NS=477.63)Sub2-45m / z=477.16(C 34 H 23 NS=477.63)Sub2-46m / z=387.2(C 26 H 29 NS=387.59)Sub2-47m / z=357.16(C 24 H 23 NS=357.52)Sub2-48m / z=445.19(C 31 H 27 NS=445.62)Sub2-49m / z=356.14(C 24 H 12 D5NS=356.50)Sub2-50m / z=393.21(C 28 H 27 NO=393.53)Sub2-51m / z=461.18(C 34 H 23 NO=461.56)Sub2-52m / z=553.19(C 40 H 27 NS=553.72)Sub2-53m / z=427.14(C 30 H 21 NS=427.57)Sub2-54m / z=461.18(C 34 H 23NO=461.56)Sub2-55m / z=385.15(C 28 H 19 NO=385.47)Sub2-56m / z=335.13(C 24 H 17 NO=335.41)Sub2-57m / z=351.11(C 24 H 17 NS=351.47)Sub2-58m / z=385.15(C 28 H 19 NO=385.47)Sub2-59m / z=385.15(C 28 H 19 NO=385.47)Sub2-60m / z=385.15(C 28 H 19 NO=385.47)Sub2-61m / z=287.2(C 19 HD 14 NO=287.42)Sub2-62m / z=345.19(C 24 H7D 10 NO=345.47)Sub2-63m / z=354.18(C 25 H 14 D5NO=354.46)Sub2-64m / z=329.18(C 23 H 23 NO=329.44)Sub2-65m / z=399.16(C 29 H 21 NO=399.49)Sub2-66m / z=399.16(C 29 H 21 NO=399.49)Sub2-67m / z=279.15(C 19 H9D6NO=279.37)Sub2-68m / z=315.16(C 22 H 21 NO=315.42)

[0202] 최종 화합물의 합성예

[0203] 1. P-1의 합성예

[0204]

[0205] After dissolving Sub1-19 (5.0 g, 13.0 mmol) in toluene (65 mL), Sub2-1 (4.3 g, 13.0 mmol), Pd2(dba)3 (0.36 g, 0.39 mmol), P(t-Bu)3 (0.16 g, 0.78 mmol), and NaOt-Bu (2.5 g, 25.9 mmol) were added, and the reaction was carried out at 80 °C. Upon completion of the reaction, the mixture was extracted with CH2Cl2 and water, and the organic layer was dried over MgSO4 and concentrated. The concentrate was then separated through a silica gel column and recrystallized to obtain 7.4 g of the product (yield 83%).

[0206] 2. Synthesis example of P-8

[0207]

[0208] (1) Synthesis example of Sub1-2

[0209] After dissolving Sub1-2-A (5.0 g, 19.3 mmol) in toluene (96 mL), Sub1-2-B (4.8 g, 19.3 mmol), Pd2(dba)3 (0.53 g, 0.58 mmol), P(t-Bu)3 (0.23 g, 1.16 mmol), and NaOt-Bu (3.7 g, 38.6 mmol) were added, and the same method as the synthesis example of P-1 was followed to obtain 6.7 g of the product (yield 81%).

[0210] (2) Synthesis example of P-8

[0211] After dissolving Sub1-2 (6.7 g, 15.7 mmol) in toluene (80 mL), Sub2-1 (5.3 g, 15.7 mmol), Pd2(dba)3 (0.43 g, 0.47 mmol), P(t-Bu)3 (0.19 g, 0.94 mmol), and NaOt-Bu (3.0 g, 31.5 mmol) were added, and the same method as the synthesis example of P-1 was followed to obtain 8.7 g of the product (yield 76%).

[0212] 3. Synthesis example of P-17

[0213]

[0214] After dissolving Sub1-3 (5.0 g, 13.5 mmol) in toluene (70 mL), Sub2-17 (4.8 g, 13.5 mmol), Pd2(dba)3 (0.37 g, 0.41 mmol), P(t-Bu)3 (0.16 g, 0.81 mmol), and NaOt-Bu (2.6 g, 27.0 mmol) were added, and the same method as the synthesis example of P-1 was followed to obtain 7.5 g of the product (yield 81%).

[0215] 4. Synthesis example of P-22

[0216]

[0217] After dissolving Sub1-23 (5.0 g, 13.0 mmol) in toluene (65 mL), Sub2-23 (4.3 g, 13.0 mmol), Pd2(dba)3 (0.36 g, 0.39 mmol), P(t-Bu)3 (0.16 g, 0.78 mmol), and NaOt-Bu (2.5 g, 25.9 mmol) were added, and the same method as the synthesis example of P-1 was followed to obtain 7.5 g of the product (yield 85%).

[0218] 5. Synthetic example of P-32

[0219]

[0220] (1) Synthesis example of Sub1-5

[0221] After dissolving Sub1-5-A (5.0 g, 19.3 mmol) in toluene (100 mL), Sub1-5-B (3.8 g, 19.3 mmol), Pd2(dba)3 (0.53 g, 0.58 mmol), P(t-Bu)3 (0.23 g, 1.16 mmol), and NaOt-Bu (3.7 g, 38.6 mmol) were added, and the same method as the synthesis example of P-1 was carried out to obtain 5.2 g of the product. (Yield 72%)

[0222] (2) Synthetic example of P-32

[0223] After dissolving Sub1-5 (5.2 g, 13.9 mmol) in toluene (70 mL), Sub2-17 (4.9 g, 13.9 mmol), Pd2(dba)3 (0.38 g, 0.42 mmol), P(t-Bu)3 (0.17 g, 0.83 mmol), and NaOt-Bu (2.7 g, 27.8 mmol) were added, and the same method as the synthesis example of P-1 was followed to obtain 7.0 g of the product (yield 73%).

[0224] 6. Synthetic example of P-38

[0225]

[0226] After dissolving Sub1-11 (5.0 g, 11.2 mmol) in toluene (55 mL), Sub2-5 (4.6 g, 11.2 mmol), Pd2(dba)3 (0.31 g, 0.34 mmol), P(t-Bu)3 (0.14 g, 0.67 mmol), and NaOt-Bu (2.2 g, 22.4 mmol) were added, and the same method as the synthesis example of P-1 was followed to obtain 7.0 g of the product (yield 76%).

[0227] 7. Synthetic example of P-45

[0228]

[0229] (1) Synthesis example of Sub1-16

[0230] After dissolving Sub1-16-A (5.0 g, 16.2 mmol) in toluene (80 mL), 1-bromo-3-chlorobenzene (3.1 g, 16.2 mmol), Pd2(dba)3 (0.44 g, 0.48 mmol), P(t-Bu)3 (0.20 g, 0.97 mmol), and NaOt-Bu (3.1 g, 32.3 mmol) were added, and the same method as the synthesis example of P-1 was followed to obtain 5.2 g of the product (yield 76%).

[0231] (2) Synthetic example of P-45

[0232] After dissolving Sub1-16 (5.2 g, 12.4 mmol) in toluene (65 mL), Sub2-1 (4.2 g, 12.4 mmol), Pd2(dba)3 (0.34 g, 0.37 mmol), P(t-Bu)3 (0.15 g, 0.74 mmol), and NaOt-Bu (2.4 g, 24.8 mmol) were added, and the same method as the synthesis example of P-1 was followed to obtain 7.0 g of the product (yield 79%).

[0233] 8. P-66 synthesis method

[0234]

[0235] After dissolving Sub1-30 (5.0 g, 9.6 mmol) in toluene (48 mL), Sub2-29 (4.1 g, 9.6 mmol), Pd2(dba)3 (0.26 g, 0.29 mmol), P(t-Bu)3 (0.12 g, 0.57 mmol), and NaOt-Bu (1.8 g, 19.2 mmol) were added, and the same method as the synthesis example of P-1 was followed to obtain 6.7 g of the product (yield 77%).

[0236] 9. P-82 synthesis method

[0237]

[0238] After dissolving Sub1-38 (5.0 g, 10.8 mmol) in toluene (54 mL), Sub2-35 (4.6 g, 10.8 mmol), Pd2(dba)3 (0.20 g, 0.32 mmol), P(t-Bu)3 (0.13 g, 0.65 mmol), and NaOt-Bu (2.1 g, 21.6 mmol) were added, and the same method as the synthesis example of P-1 was followed to obtain 6.9 g of the product (yield 75%).

[0239] 10. P-99 synthesis method

[0240]

[0241] After dissolving Sub1-45 (5.0 g, 11.2 mmol) in toluene (56 mL), Sub2-54 (7.2 g, 11.2 mmol), Pd2(dba)3 (0.31 g, 0.34 mmol), P(t-Bu)3 (0.14 g, 0.67 mmol), and NaOt-Bu (2.2 g, 22.4 mmol) were added, and the same method as the synthesis example of P-1 was followed to obtain 7.5 g of the product (yield 77%).

[0242] 11. P-105 synthesis method

[0243]

[0244] After dissolving Sub1-16 (5.0 g, 11.9 mmol) in toluene (60 mL), Sub2-56 (4.0 g, 11.9 mmol), Pd2(dba)3 (0.33 g, 0.36 mmol), P(t-Bu)3 (0.14 g, 0.71 mmol), and NaOt-Bu (2.3 g, 23.8 mmol) were added, and the same method as the synthesis example of P-1 was followed to obtain 6.2 g of the product (yield 73%).

[0245] The FD-MS values ​​of the compounds of the present invention manufactured according to the above synthetic examples are as shown in Table 3 below.

[0246] Compound FD-MS Compound FD-MSP-1 m / z = 684.22 (C 48 H 32 N2OS=684.86)P-2m / z=760.25(C 54 H 36 N2OS=760.96)P-3m / z=734.24(C 52 H 34 N2OS=734.92)P-4m / z=734.24(C 52 H 34 N2OS=734.92)P-5m / z=668.25(C 48 H 32 N2O2=668.80)P-6m / z=684.22(C 48 H 32N2OS=684.86)P-7m / z=700.2(C 48 H 32 N2S2=700.92)P-8m / z=724.31(C 52 H 40 N2O2=724.90)P-9m / z=760.25(C 54 H 36 N2OS=760.96)P-10m / z=664.25(C 46 H 36 N2OS=664.87)P-11m / z=734.24(C 52 H 34 N2OS=734.92)P-12m / z=690.27(C 48 H 38 N2OS=690.91)P-13m / z=700.2(C 48 H 32 N2S2=700.92)P-14m / z=776.23(C 54 H 36 N2S2=777.02)P-15m / z=750.22(C 52 H 34 N2S2=750.98)P-16m / z=750.22(C 52 H 34 N2S2=750.98)P-17m / z=684.22(C 48 H 32 N2OS=684.86)P-18m / z=684.22(C 48 H 32 N2OS=684.86)P-19m / z=668.25(C 48 H 32 N2O2=668.80)P-20m / z=776.23(C 54 H 36 N2S2=777.02)P-21m / z=776.23(C 54 H 36 N2S2=777.02)P-22m / z=680.23(C 46 H 36 N2S2=680.93)P-23m / z=718.25(C 49 H 38 N2S2=718.98)P-24m / z=750.22(C 52 H 34N2S2=750.98)P-25m / z=684.22(C 48 H 32 N2OS=684.86)P-26m / z=760.25(C 54 H 36 N2OS=760.96)P-27m / z=760.25(C 54 H 36 N2OS=760.96)P-28m / z=760.25(C 54 H 36 N2OS=760.96)P-29m / z=700.2(C 48 H 32 N2S2=700.92)P-30m / z=684.22(C 48 H 32 N2OS=684.86)P-31m / z=668.25(C 48 H 32 N2O2=668.80)P-32m / z=688.25(C 48 H 28 D4N2OS=688.88)P-33m / z=760.25(C 54 H 36 N2OS=760.96)P-34m / z=784.25(C 56 H 36 N2OS=784.98)P-35m / z=796.35(C 56 H 48 N2OS=797.07)P-36m / z=742.3(C 52 H 42 N2OS=742.98)P-37m / z=668.25(C 48 H 32 N2O2=668.80)P-38m / z=820.31(C 60 H 40 N2O2=820.99)P-39m / z=718.26(C 52 H 34 N2O2=718.86)P-40m / z=718.26(C 52 H 34 N2O2=718.86)P-41m / z=684.22(C 48 H 32 N2OS=684.86)P-42m / z=684.22(C 48 H 32N2OS=684.86)P-43m / z=700.2(C 48 H 32 N2S2=700.92)P-44m / z=744.28(C 54 H 36 N2O2=744.89)P-45m / z=718.26(C 52 H 34 N2O2=718.86)P-46m / z=718.26(C 52 H 34 N2O2=718.86)P-47m / z=718.26(C 52 H 34 N2O2=718.86)P-48m / z=826.36(C 60 H 46 N2O2=827.04)P-49m / z=820.31(C 60 H 40 N2O2=820.99)P-50m / z=718.26(C 52 H 34 N2O2=718.86)P-51m / z=674.29(C 48 H 38 N2O2=674.84)P-52m / z=648.28(C 46 H 36 N2O2=648.81)P-53m / z=700.45(C 48 D 32 N2O2=700.99)P-54m / z=687.37(C 48 H 13 D 19 N2O2=687.91)P-55m / z=830.37(C 60 H 30 D 10 N2O2=831.05)P-56m / z=724.31(C 52 H 40 N2O2=724.90)P-57m / z=794.29(C 58 H 38 N2O2=794.95)P-58m / z=794.29(C 58 H 38 N2O2=794.95)P-59m / z=679.32(C 48 H 21 D 11N2O2=679.86)P-60m / z=704.34(C 50 H 44 N2O2=704.91)P-61m / z=760.25(C 54 H 36 N2OS=760.96)P-62m / z=760.25(C 54 H 36 N2OS=760.96)P-63m / z=810.27(C 58 H 38 N2OS=811.01)P-64m / z=810.27(C 58 H 38 N2OS=811.01)P-65m / z=744.28(C 54 H 36 N2O2=744.89)P-66m / z=912.32(C 66 H 44 N2OS=913.15)P-67m / z=776.23(C 54 H 36 N2S2=777.02)P-68m / z=800.34(C 58 H 44 N2O2=801.00)P-69m / z=760.25(C 54 H 36 N2OS=760.96)P-70m / z=760.25(C 54 H 36 N2OS=760.96)P-71m / z=734.24(C 52 H 34 N2OS=734.92)P-72m / z=810.27(C 58 H 38 N2OS=811.01)P-73m / z=750.22(C 52 H 34 N2S2=750.98)P-74m / z=852.26(C 60 H 40 N2S2=853.11)P-75m / z=826.25(C 58 H 38 N2S2=827.08)P-76m / z=826.25(C 58 H 38 N2S2=827.08)P-77m / z=778.3(C 55 H 42N2OS=779.01)P-78m / z=704.29(C 49 H 40 N2OS=704.93)P-79m / z=648.28(C 46 H 36 N2O2=648.81)P-80m / z=916.39(C 64 H 56 N2S2=917.29)P-81m / z=776.23(C 54 H 36 N2S2=777.02)P-82m / z=852.26(C 60 H 40 N2S2=853.11)P-83m / z=680.23(C 46 H 36 N2S2=680.93)P-84m / z=826.25(C 58 H 38 N2S2=827.08)P-85m / z=886.3(C 64 H 42 N2OS=887.11)P-86m / z=796.35(C 56 H 48 N2OS=797.07)P-87m / z=766.3(C 54 H 42 N2OS=767.00)P-88m / z=792.32(C 56 H 44 N2OS=793.04)P-89m / z=705.23(C 48 H 27 D5N2S2=705.95)P-90m / z=742.3(C 52 H 42 N2OS=742.98)P-91m / z=794.29(C 58 H 38 N2O2=794.95)P-92m / z=890.33(C 64 H 38 D4N2OS=891.14)P-93m / z=836.29(C 60 H 40 N2OS=837.05)P-94m / z=760.25(C 54 H 36 N2OS=760.96)P-95m / z=760.25(C 54 H 36N2OS=760.96)P-96m / z=760.25(C 54 H 36 N2OS=760.96)P-97m / z=744.28(C 54 H 36 N2O2=744.89)P-98m / z=820.31(C 60 H 40 N2O2=820.99)P-99m / z=870.32(C 64 H 42 N2O2=871.05)P-100m / z=794.29(C 58 H 38 N2O2=794.95)P-101m / z=810.27(C 58 H 38 N2OS=811.01)P-102m / z=810.27(C 58 H 38 N2OS=811.01)P-103m / z=826.25(C 58 H 38 N2S2=827.08)P-104m / z=870.32(C 64 H 42 N2O2=871.05)P-105m / z=718.26(C 52 H 34 N2O2=718.86)P-106m / z=718.26(C 52 H 34 N2O2=718.86)P-107m / z=718.26(C 52 H 34 N2O2=718.86)P-108m / z=826.36(C 60 H 46 N2O2=827.04)P-109m / z=744.28(C 54 H 36 N2O2=744.89)P-110m / z=718.26(C 52 H 34 N2O2=718.86)P-111m / z=718.26(C 52 H 34 N2O2=718.86)P-112m / z=718.26(C 52 H 34 N2O2=718.86)P-113m / z=636.42(C 43 D30 N2O2=636.91)P-114m / z=687.37(C 48 H 13 D 19 N2O2=687.91)P-115m / z=768.36(C 55 H 28 D 10 N2O2=768.98)P-116m / z=662.29(C 47 H 38 N2O2=662.83)P-117m / z=732.28(C 53 H 36 N2O2=732.88)P-118m / z=732.28(C 53 H 36 N2O2=732.88)P-119m / z=612.27(C 43 H 24 D6N2O2=612.76)P-120m / z=662.29(C 47 H 38 N2O2=662.83)

[0247] Although the above has been described with respect to exemplary synthetic examples of the present invention represented by Chemical Formula 1 or references, these are all based on Buchwald-Hartwig cross coupling reaction, Miyaura boration reaction, Suzuki cross-coupling reaction, Intramolecular acid-induced cyclization reaction (J. mater. Chem. 1999, 9, 2095), Pd(II)-catalyzed oxidative cyclization reaction (Org. Lett. 2011, 13, 5504), and PPh3-mediated reductive cyclization reaction (J. Org. Chem. 2005, 70, 5014), and it will be easily understood by those skilled in the art that the above reaction proceeds even if a substituent other than the substituent specified in the specific synthetic example is combined.

[0248] [Example 1] Green organic light-emitting device (luminescent auxiliary layer)

[0249] A hole injection layer having a thickness of 60 nm was formed by vacuum-depositing 4,4',4"-tris[2-naphthyl(phenyl)amino]triphenylamine (hereinafter abbreviated as 2-TNATA) on an ITO layer (anode) formed on a glass substrate, and then a hole transport layer was formed by vacuum-depositing N,N'-bis(1-naphthalenyl)-N,N'-bis-phenyl-(1,1'-biphenyl)-4,4'-diamine (hereinafter abbreviated as NPB) on the hole injection layer having a thickness of 60 nm.

[0250] Next, the compound P-1 of the present invention was vacuum-deposited on the hole transport layer to a thickness of 20 nm to form a light-emitting auxiliary layer, and then 4,4'-N,N'-dicarbazole-biphenyl (hereinafter abbreviated as 'CBP') was used as a host material, and tris(2-phenylpyridine)-iridium (hereinafter abbreviated as 'Ir(ppy)3') was used as a dopant material, and the dopant was doped at a weight ratio of 95:5 to form a light-emitting layer with a thickness of 30 nm.

[0251] Next, (1,1'-biphenyl-4-olato)bis(2-methyl-8-quinolinolato)aluminum (hereinafter abbreviated as BAlq) was vacuum-deposited on the light-emitting layer to form a hole-blocking layer with a thickness of 10 nm, and tris(8-quinolinol)aluminum (hereinafter abbreviated as Alq3) was vacuum-deposited on the hole-blocking layer to a thickness of 40 nm to form an electron-transporting layer. Thereafter, LiF was deposited on the electron-transporting layer to form an electron-injection layer with a thickness of 0.2 nm, and then Al was deposited to form a cathode with a thickness of 150 nm.

[0252] [Example 2] to [Example 24]

[0253] An organic light-emitting device was manufactured in the same manner as Example 1, except that the compound of the present invention described in Table 4 below was used instead of the compound P-1 of the present invention as a light-emitting auxiliary layer material.

[0254] [Comparative Example 1] to [Comparative Example 4]

[0255] An organic light-emitting device was manufactured in the same manner as in Example 1, except that one of Comparative Compounds A to D was used instead of Compound P-1 of the present invention as the light-emitting auxiliary layer material.

[0256] Comparative Compound A <Comparative Compound B>

[0257]

[0258] Comparative Compound C Comparative Compound D

[0259]

[0260] The organic electroluminescence devices manufactured by the examples and comparative examples were applied with a forward bias DC voltage and the electroluminescence (EL) characteristics were measured using a PR-650 from Photoresearch, and 5000 cd / m 2 T95 was measured using a life-span measuring device manufactured by Maxscience at a reference luminance. The measurement results are shown in Table 4 below.

[0261] These measuring devices are unaffected by daily variations in deposition rate, vacuum quality, or other parameters, and can evaluate new performance compared to reference compounds under identical conditions. Since each batch contains four identically prepared OLEDs containing the reference compound, and the performance of a total of 12 OLEDs is evaluated in three batches, the experimental results obtained in this manner are statistically significant.

[0262] Compound driving voltage current (mA / cm) 2 ) Luminance (cd / m 2) Efficiency (cd / A) T (95) Comparative Example 1 Comparative Compound A 6.0 13.25 000.03 7.9 103.1 Comparative Example 2 Comparative Compound B 5.9 13.4 5000.03 7.2 101.8 Comparative Example 3 Comparative Compound C 5.8 13.9 5000.03 6.0 102.6 Comparative Example 4 Comparative Compound D6.014.25000.035.3101.1Embodiment 1P-15.29.95000.050.3122.5Embodiment 2P-25.010.65000.047.3123.6Embodiment 3P-55.29.75000.051.6125.9Embodiment 4P-85.29.55000.052.5124.4Embodiment 5P-185.09.95000.050.6131.1Embodiment 6P-194.910.85000.0 46.5127.2 Example 7P-315.010.55000.047.8127.9 Example 8P-375.010.45000.048.1129.6 Example 9P-385.010.35000.048.4130.1 Example 10P-415.110.25000.048.9129.4 Example 11P-434.910.75000.046.9126.1 Example 12P-455.110.25000.049.2 128.8 Example 13P-515.39.35000.053.9128.3 Example 14P-525.39.25000.054.4126.5 Example 15P-595.110.15000.049.7131.3 Example 16P-615.09.75000.051.6100.3 Example 17P-765.19.35000.053.5101.1 Example 18P-775.19.55000.052.9103.1 Example 19P-825.310.85000.046.2121.6 Example 20P-855.310.75000.046.9121.9 Example 21P-865.310.65000.047.0122.3 Example 22P-955.19.75000.051.7101.4 Example 23P-1055.310.65000.047.2121.5 Example 24P-1195.310.75000.046.6122.2

[0263] As can be seen from Table 4 above, when the compound of the present invention is used as a light-emitting auxiliary layer material, the driving voltage of the organic electric device can be significantly lowered and the efficiency and lifespan can be significantly improved compared to when one of Comparative Compounds A to D is used (Comparative Examples 1 to 4). The compound of Chemical Formula 1 of the present invention has a diamine skeleton and Ar 1 , Ar 2 The fact that it is an aryl group and does not contain a fluorenyl group, that it is bonded to the nitrogen of the amine at a specific position (position 1) such as dibenzothiophene or dibenzofuran of chemical formula A, Ar 3 It has the characteristic that it cannot be a heterocyclic group with an aryl group, alkyl group, or aliphatic ring group.

[0264] Comparative compounds A to D are similar to the present invention in that they have a diamine skeleton and a structure in which dibenzofuran or dibenzothiophene is substituted for amine, but Comparative compounds A and C have Ar of chemical formula 1 of the present invention. 1 , Ar 2 Comparative compound B has a difference in that the substituent corresponding to is fluorene and the position at which the dibenzothiophene corresponding to the chemical formula A of the present invention is bonded to the nitrogen of the amine, and comparative compound D has a difference in that the dibenzofuran corresponding to the chemical formula A of the present invention is bonded to the nitrogen of the amine, and comparative compound D has a difference in that the substituent corresponding to is fluorene and the position at which the dibenzothiophene corresponding to the chemical formula A of the present invention is bonded to the nitrogen of the amine. 3 The difference is that the corresponding substituent is a heterocycle.

[0265] In order to determine the influence of these differences in substituents on the characteristics of the device, the HOMO levels of Compounds A to C and Compounds P-1 and P-38 of the present invention were measured using the DFT method (B3LYP / 6-31g(D)) of the Gaussian program. The measurement results are shown in Table 5 below.

[0266] Comparative Compound A Comparative Compound B Comparative Compound CP-1P-38 HOMO (eV) -4.91 - 4.87 - 4.85 - 4.96 - 4.96

[0267] As can be seen from the above Table 5, it can be seen that the HOMO energy level of the compound of the present invention is formed deeper (lower) than that of Comparative Compounds A to C. Therefore, when the compound of the present invention is used as a material for a light-emitting auxiliary layer, it is possible to suppress hole injection into the light-emitting auxiliary layer, and thus it appears to be effective in reducing capacitance. In addition, since the balance of holes and electrons (charge balance) is improved through hole accumulation between the hole transport layer and the light-emitting auxiliary layer, it appears to affect efficiency and lifespan. In the case of Comparative Compound D, the Ar of the present invention is formed on dibenzofuran or dibenzothiophene having an amine group bonded at position 1. 3 It differs from the compound of the present invention in that the heterocyclic group carbazole is substituted with a substituent corresponding to . Therefore, it appears that the energy level of the comparative compound D is formed similarly to that of the compound of the present invention, but since the volume of the molecule itself is relatively large, the intermolecular distance increases during device deposition compared to the compound of the present invention, resulting in a difference in hole transport ability and, as a result, a significant difference in device characteristics.

[0268] From the above Tables 4 and 5, it can be confirmed that the compound of the present invention, which satisfies all complex factors such as the type of substituent and the substitution position of the substituent, exhibits a remarkable effect in an organic electric device compared to other comparative compounds, even though the structure of the compound used as the light-emitting auxiliary layer is similar, and through this, it can be seen that the compound of the present invention exhibits a remarkable effect in an organic electric device compared to simple structural isomers or compounds having a similar structure not described in the present specification.

[0269] These results suggest that even if the molecular components are similar, the properties of the compound, such as hole characteristics, light efficiency characteristics, energy level, hole injection and mobility characteristics, charge balance of holes and electrons, volume density, and intermolecular distance, can differ significantly to an extent that is difficult to predict depending on the type and position of the substituted substituent, and that the performance of the device can vary not only due to a single component but also due to complex factors.

[0270] The evaluation results of the above-described device fabrication described the device characteristics in which the compound of the present invention was applied only to the light-emitting auxiliary layer, but the compound of the present invention may be applied to the hole transport layer or the buffer layer, or may be applied to both the hole transport layer, the buffer layer, and the light-emitting auxiliary layer.

[0271] The above description is merely illustrative of the present invention. Those skilled in the art will appreciate that various modifications may be made without departing from the essential characteristics of the present invention. The scope of protection of the present invention should be construed in accordance with the claims below, and all techniques within the scope equivalent thereto should be construed as being included within the scope of the present invention.

Claims

1. A compound represented by the following chemical formula 1: <Chemical Formula 1> <Chemical Formula A> In the above chemical formula 1, A is chemical formula A, X 1 and X 2 are O or S respectively, Ar 1 and Ar 2 are independently C6~C 60 is an aryl group, Ar 3 Silver C6~C 60 Aryl group of; C3~C 60 Aliphatic ring group of; and C1~C 20 is selected from the group consisting of alkyl groups, Ar 1 Inland Ar 3 are respectively deuterium; C1-C 20 alkyl group of; C6-C 30 Aryl group of; and C6-C substituted with deuterium 30 may be substituted with one or more substituents selected from the group consisting of aryl groups, R 1 Inland R 5 are independently hydrogen; deuterium; halogen; cyano group; silane group; C6~C 60 Aryl group of; fluorenyl group; C2~C containing at least one heteroatom among O, N, S, Si and P 60 Heterocyclic group of; C3~C 60 Aliphatic ring group; C6~C 60 Aromatic ring and C3~C 60 Fused ring group of aliphatic ring; C1~C 20 Alkyl group of; C2~C 20 Alkenyl group of; C2~C 20 Alkynyl group of; C1~C 20 Alkoxy group of; and C6~C 60 is selected from the group consisting of aryloxy groups, and adjacent groups can be combined with each other to form a ring, provided that adjacent R 5 Except when they combine with each other to form a ring, a and e are integers from 0 to 4, respectively; b, c, and d are integers from 0 to 3, respectively; R 1 Inland R 5 are respectively deuterium; halogen; C1-C 20 Alkyl group or C6-C 20 Silane group substituted or unsubstituted with an aryl group; C1-C 20 Alkyl group or C6-C 20 Phosphine oxide substituted or unsubstituted with an aryl group; cyano group; C1-C 20 Alkoxy group of; C6-C 30 Aryloxy group of; C1-C 20 alkyl group of; C2-C 20 alkenyl group of; C2-C 20 Alkynyl group of; C6-C 30 Aryl group of; C6-C substituted with deuterium 30 Aryl group of; fluorenyl group; C3-C 30 Aliphatic ring group; C6-C 30 Aromatic ring and C3-C 30 A fused ring group of an aliphatic ring; and C2-C containing at least one heteroatom among O, N, S, Si and P. 30 It may be substituted with one or more substituents selected from the group consisting of heterocyclic groups, and adjacent substituents may be combined with each other to form a ring, and hydrogen of the substituents may be replaced with deuterium.

2. In paragraph 1, The above chemical formula 1 is a compound characterized by being represented by one of the following chemical formulas 1-1 to 1-4: <Chemical Formula 1-1> <Chemical Formula 1-2> <Chemical Formula 1-3> <Chemical Formula 1-4> In the above chemical formulas 1-1 to 1-4, A, X 1 , Ar 1 , Ar 2 , R 1 , R 2 , R 5 , a, b, e are as defined in paragraph 1.

3. In paragraph 1, The above chemical formula A is a compound characterized by being one of the following chemical formulas A-1 to A-4: <Chemical Formula A-1> <Chemical Formula A-2> <Chemical Formula A-3> <Chemical Formula A-4> In the above chemical formulas A-1 to A-4, X 2 , Ar 3 , R 3 , R 4 , c, d are as defined in paragraph 1.

4. In paragraph 1, Ar 1 Inland Ar 3 A compound characterized in that at least one of the compounds is selected from the group consisting of the following chemical formulae Ar-1 to Ar-4: <Chemical Formula Ar-1> <Chemical Formula Ar-2> <Chemical Formula Ar-3> <Chemical Formula Ar-4> In the above chemical formulas Ar-1 to Ar-4, R 6 Inland R 9 are independently hydrogen; deuterium; C1-C 20 alkyl group of; C6-C 30 Aryl group of; and C6-C substituted with deuterium 30 It is selected from the group consisting of aryl groups, and adjacent groups are bonded to each other and C6-C 30 , f and h are each an integer from 0 to 5, g is an integer from 0 to 4, and i is an integer from 0 to 7.

5. In an organic electric device including a first electrode, a second electrode, and an organic layer between the first electrode and the second electrode, An organic electric device characterized in that the organic layer comprises the compound of claim 1.

6. In paragraph 5, An organic electric device characterized in that the organic layer includes a light-emitting auxiliary layer, and the light-emitting auxiliary layer includes the compound of claim 1.

7. In paragraph 5, An organic electric device characterized in that the organic layer comprises two or more stacks including a hole transport layer, a light-emitting layer, and an electron transport layer sequentially formed on the first electrode.

8. A display device including the organic electric element of paragraph 5; and An electronic device including a control unit that drives the display device.

9. A compound obtained by depositing an organic material layer in the manufacturing process of an organic electronic device, recovering the material of the organic material layer from the deposition equipment, and then purifying it. A compound characterized in that the compound is a compound represented by the chemical formula 1 of claim 1.

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