Compound for organic electric element, organic electric element using same, and electronic device having 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. The inclusion of the compound represented by chemical formula 1 in the organic material layer can lower the driving voltage of the organic electric element and improve the light emission efficiency and lifespan thereof.

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 capable of lowering the driving voltage of a device and improving 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 a compound according to an embodiment of the present invention, 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 an organic light-emitting device according to 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] As used herein, the terms "aryl group" and "arylene group", unless otherwise stated, each have 6 to 60 carbon atoms, but are 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 rings such as "heteroaryl group" or "heteroarylene group" but also non-aromatic rings, and unless otherwise stated means a ring having 2 to 60 carbon atoms each containing one or more heteroatoms, but is not limited thereto. 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', or may 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, or it may 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 fused rings. 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 in this specification, substituents such as aryl group, arylene group, fluorenyl group, fluorenylene group, heterocyclic group, aliphatic 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; 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; 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] 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.

[0048] 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.

[0049] 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.

[0050] 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.

[0051] Figures 1 to 3 are exemplary diagrams of organic electric devices according to embodiments of the present invention.

[0052] 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).

[0053] 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.

[0054] 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.

[0055] 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).

[0056] 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.

[0057] 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).

[0058] 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.

[0059] Referring to FIG. 2, an organic electric device (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.

[0060] 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).

[0061] 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.

[0062] 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.

[0063] 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).

[0064] 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.

[0065] 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.

[0066] 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.

[0067] 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).

[0068] 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.

[0069] 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 is preferably used as a material for the light-emitting auxiliary layer (220) or / and the light-efficiency improvement layer (180), and more preferably, as a material for the light-emitting auxiliary layer (220).

[0070] 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.

[0071] 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.

[0072] 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.

[0073] 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.

[0074] 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.

[0075] 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.

[0076] 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.

[0077] Hereinafter, a compound according to one aspect of the present invention will be described.

[0078] A compound according to one aspect of the present invention is represented by the following chemical formula 1.

[0079] <Chemical Formula 1> <Chemical Formula A>

[0080]

[0081] In the above chemical formula, each symbol is defined as follows.

[0082] In the above chemical formula 1, A is chemical formula A.

[0083] X is O, S, C(R1)(R2) or Si(R3)(R4).

[0084] Ar 1 Silver C6~C 60 C2~C containing an arylene group or at least one heteroatom among O, N, S, Si and P 60 It is a heterocyclic group.

[0085] Ak 1 is C3~C 60 is an aliphatic ring, and Ak 2 and Ak 3 are independently of each other C1~C 20 Alkyl group or C3~C 60 It is a fatty acid ring.

[0086] R 1 Inland R 4 are independently hydrogen; deuterium; halogen; cyano group; nitro group; C6~C 60Aryl 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 R 1 R in pairs or neighboring pairs 2 They can combine with each other to form rings.

[0087] a and d are each integers from 0 to 4, b and c are each integers from 0 to 3, and if they are integers greater than or equal to 2, then multiple R 1 Each, multiple R 2 Each, multiple R 3 Each, multiple R 4 Each is either the same or different from the other.

[0088] Neighboring units, for example, neighboring R 1 Kiri, neighboring R 2 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.

[0089] When adjacent groups combine with each other to form an aromatic ring group, the aromatic ring is, for example, C6~C 20 , C6~C 18 , C6~C16 , C6~C 14 , C6~C 13 , C6~C 12 , C6~C 10 , C6, C 10 , C 12 , C 14 , C 15 , C 16 , C 18 It may be an aryl ring, such as benzene, naphthalene, anthracene, phenanthrene, pyrene, etc.

[0090] When adjacent groups combine with each other to form a heterocyclic ring, the heterocyclic group is C2~C 24 , C2~C 23 , C2~C 22 , C2~C 21 , C2~C 20 , C2~C 19 , C2~C 18 , C2~C 17 , C2~C 16 , C2~C 15 , C2~C 14 , C2~C 13 , C2~C 12 , C2~C 11 , C2~C 10 , C2~C9, C2~C8, C2~C7, C2~C6, C2~C5, C2~C4, C2~C3, C2, C3, C4, C5, C6, C7, C8, C9, C 10 , C 11 , C 12 , C 13 , C 14 , C 15 , C 16 , C 17 , C 18 , C 19 , C 20 , C 21 , C 22 , C 23 , C 24It may be a heterocyclic group such as, etc. The heterocyclic group may be a single ring containing a heteroatom, a condensed ring in which a heterocycle is condensed with a heterocycle, or a condensed ring in which a hydrocarbon ring such as an aliphatic ring or an aromatic ring is condensed with a heterocycle, and may be, for example, furan, thiophene, benzothiophene, benzofuran, dibenzothiophene, dibenzofuran, etc.

[0091] R1 to R4 are independently 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 It is selected from the group consisting of aryloxy groups, and adjacent groups can combine with each other to form a ring. Here, 'adjacent groups' means R1 and R2 or R3 and R4, and when these combine with each other to form a ring, a spiro compound is formed.

[0092] When R1 and R2 are combined with each other or R3 and R4 are combined with each other to form an aliphatic ring, the aliphatic ring is 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~C17 , 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, C5~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 a cycloalkyl group, and may include one or more double bonds within the ring. Specifically, it may be a cyclopentenyl group, a cyclohexenyl group, a cyclopentanyl group, a cyclohexanyl group, an indenyl group, a tetralin group, a norbornyl group, an adamantyl group, etc.

[0093] When R1 and R2 are bonded to each other to form fluorenyl, a spiro compound sharing C with the fluorene to which R1 and R2 are bonded, such as 9,9'-spirobifluorene, can be formed.

[0094] L 1 Inland L 3 are independently of each other and are single bonds; C6~C 60 C2~C containing an arylene group of; and at least one heteroatom of O, N, S, Si and P 60 is selected from the group consisting of heterocyclic groups.

[0095] The above Ar 1 , R 1 Inland R 4 , at least one of R1 to R4 is an aryl group, or L 1 Inland L 3 If at least one of the silver is an arylene group, the aryl group or arylene 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 or an arylene group, and specifically, it may be phenyl, biphenyl, naphthyl, terphenyl, phenanthrene, triphenylene, etc.

[0096] The above Ar 1 , R 1 Inland R 4 , R1 to R4, L 1 Inland L 3 If at least one of them is a heterocyclic group, the heterocyclic group is, for example, C2~C 30 , C2~C 29 , C2~C 28 , C2~C 27 , C2~C 26 , C2~C 25 , C2~C 24 , C2~C 23 , C2~C 22 , C2~C 21 , C2~C 20 , C2~C 19 , C2~C 18 , C2~C 17 , C2~C 16 , C2~C 15 , C2~C 14, C2~C 13 , C2~C 12 , C2~C 11 , C2~C 10 , C2~C9, C2~C8, C2~C7, C2~C6, C2~C5, C2~C4, C2~C3, C2, C3, C4, C5, C6, C7, C8, C9, C 10 , C 11 , C 12 , C 13 , C 14 , C 15 , C 16 , C 17 , C 18 , C 19 , C 20 , C 21 , C 22 , C 23 , C 24 , C 25 , C 26 , C 27 , C 28 , C 29It may be a heterocyclic group such as, and specifically, pyridine, pyrimidine, pyrazine, pyridazine, triazine, furan, pyrrole, indene, indole, phenyl-indole, benzoindole, phenyl-benzoindole, pyrazinoindole, quinoline, isoquinoline, benzoquinoline, pyridoquinoline, quinazoline, benzoquinazoline, dibenzoquinazoline, phenanthroquinazoline, quinoxaline, benzoquinoxaline, dibenzoquinoxaline, benzofuran, naphthobenzofuran, dibenzofuran, dinaphthofuran, thiophene, benzothiophene, dibenzothiophene, naphthobenzothiophene, dinaphthothiophene, carbazole, phenyl-carbazole, benzocarbazole, phenyl-benzocarbazole, Naphthyl-benzocarbazole, dibenzocarbazole, indolocarbazole, benzofuropyridine, benzothiopyridine, benzofuropyridine, benzothiopyrimidine, benzofuropyrimidine, benzothiopyrazine, benzofuropyrazine, benzimidazole, benzothiazole, benzoxazole, benzosilole, phenanthroline, dihydro-phenylphenazine, 10-phenyl-10H-phenoxazine, phenoxazine, phenothiazine, dibenzodioxin, benzodibenzodioxin, thianthrene, 9,9-dimethyl-9H-xanthrene, 9,9-dimethyl-9H-thioxanthrene, dihydrodimethylphenylacridine, spiro[fluorene-9,9'-xanthene], etc.

[0097] The above Ak 1 Inland Ak 3 , R 1 Inland R 4 , if at least one of R1 to R4 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~C16 , C3~C 15 , C3~C 14 , C3~C 13 , C3~C 12 , C3~C 11 , C3~C 10 , C3~C8, C3~C6, C3, C4, C5, C6, C7, C8, C9, 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 cyclopropane, cyclobutane, cyclopentane, cyclohexane, bicyclo[2.2.1]heptane, adamantyl group, etc.

[0098] The above Ak 2 , Ak 3 , R 1 Inland R 4 , when at least one of R1 to R4 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 t-butyl group, etc.

[0099] The above aryl group, arylene group, fluorenyl group, heterocyclic group, aliphatic ring group, fused ring group, alkyl group, alkenyl group, alkynyl group, alkoxy group, aryloxy group, and the ring formed by bonding adjacent groups to each other are each composed of 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; nitro group; C1-C 20 Alkylthio group of; C1-C 20 Alkoxy group of; C6-C 30Aryloxy group of; C6-C 30 Arylthio 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; 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.

[0100] When at least one of the above 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, and ring formed by bonding adjacent groups is substituted with 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 , C17 , C 18 It can be an aryl group such as .

[0101] When at least one of the above 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, and rings formed by bonding adjacent groups to each other is substituted with 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, C3, C4, C5, C6, C7, C8, C9, C 10 , C 11 , C 12 , C 13 , C 14 , C 15 , C 16 , C 17 , C 18 It may be an aliphatic ring such as the back.

[0102] When at least one of the above 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, and ring formed by bonding adjacent groups to each other 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. can be alkyl groups.

[0103] When at least one of the above 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, and ring formed by bonding adjacent groups is substituted with an alkenyl group, the alkenyl group is, for example, C2~C 20 , C2~C 10 , it can be an alkenyl group such as C2~C4, C2, C3, C4, etc.

[0104] The above chemical formula 1 can be represented by one of the following chemical formulas 2-1 to 2-4.

[0105] <Chemical Formula 2-1> <Chemical Formula 2-2>

[0106]

[0107] <Chemical Formula 2-3> <Chemical Formula 2-4>

[0108]

[0109] In the above chemical formulas 2-1 to 2-4, A, X, R 1 , R 2 , L 1 Inland L 3 , Ar 1 , Ak 1 , a and b are as defined in chemical formula 1.

[0110] The above chemical formula A can be selected from the group consisting of the following chemical formulas A-1 to A-12.

[0111] <Chemical Formula A-1> <Chemical Formula A-2> <Chemical Formula A-3> <Chemical Formula A-4>

[0112]

[0113] <Chemical Formula A-5> <Chemical Formula A-6> <Chemical Formula A-7> <Chemical Formula A-8>

[0114]

[0115] <Chemical Formula A-9> <Chemical Formula A-10> <Chemical Formula A-11> <Chemical Formula A-12>

[0116]

[0117] In the above chemical formulas A-1 to A-12, Ak 2 , Ak 3 , R 3 , R 4 , c, d are as defined in chemical formula 1.

[0118] Ak 1 Silver may be selected from the group consisting of the following chemical formulas 4-1 to 4-3, and Ak 2 and Ak 3 At least one of the compounds may be selected from the group consisting of the following chemical formulae 5-1 to 5-7.

[0119] <Chemical Formula 4-1> <Chemical Formula 4-2> <Chemical Formula 4-3>.

[0120]

[0121] <Chemical Formula 5-1> <Chemical Formula 5-2> <Chemical Formula 5-3> <Chemical Formula 5-4>

[0122]

[0123] <Chemical Formula 5-5> <Chemical Formula 5-6> <Chemical Formula 5-7>

[0124] .

[0125] Ar 1 may be selected from the group consisting of the following chemical formulas Ar-1 to Ar-9.

[0126] <Chemical formula Ar-1> <Chemical formula Ar-2> <Chemical formula Ar-3>

[0127]

[0128] <Chemical formula Ar-4> <Chemical formula Ar-5> <Chemical formula Ar-6>

[0129]

[0130] <Chemical formula Ar-7> <Chemical formula Ar-8> <Chemical formula Ar-9>

[0131]

[0132] In the above chemical formula, R 5 and R 6 are independently hydrogen, 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; nitro group; C1-C 20 Alkylthio group of; C1-C 20 Alkoxy group of; C6-C 30 Aryloxy group of; C6-C 30 Arylthio 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; 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 is selected from the group consisting of heterocyclic groups, and adjacent groups can combine with each other to form a ring, and e and f are each integers from 0 to 4.

[0133] Specifically, the compound represented by the above chemical formula 1 may be one of the following compounds, but is not limited thereto.

[0134]

[0135]

[0136]

[0137]

[0138]

[0139]

[0140]

[0141]

[0142]

[0143]

[0144]

[0145]

[0146]

[0147]

[0148]

[0149]

[0150]

[0151]

[0152]

[0153]

[0154]

[0155]

[0156] .

[0157] 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.

[0158] 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.

[0159] In another aspect, the present invention provides a method for recovering a compound represented by Chemical Formula 1, 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.

[0160] 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.

[0161] 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.

[0162] 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.

[0163] 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.

[0164] 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.

[0165] 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.

[0166] 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.

[0167] 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.

[0168] 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.

[0169] 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.

[0170] 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 with reference to examples, but the present invention is not limited to the following examples.

[0171] [Synthesis example]

[0172] The compound represented by chemical formula 1 according to the present invention (final product) can be prepared by the following reaction scheme 1, but is not limited thereto.

[0173] <Reaction Scheme 1> (Hal 1 is I, Br or Cl)

[0174]

[0175] Synthesis example of Sub1

[0176] Sub1 of the above reaction scheme 1 can be synthesized by the reaction path of the following reaction scheme 2, but is not limited thereto.

[0177] <Reaction Scheme 2> (Hal 2 , Hal 3 is I, Br or Cl)

[0178]

[0179] 1. Sub1-2 synthesis example

[0180]

[0181] In a round-bottomed flask, add 2-bromo-1-chloro-3-methylbenzene (10.2 g, 50.0 mmol), (2-(tert-butyl)phenyl)boronic acid (8.9 g, 50.0 mmol), Pd(PPh3)4 (1.73 g, 1.5 mmol), NaOH (6.0 g, 150 mmol), THF (120 mL), and water (40 mL), and reflux. Upon completion of the reaction, extract with THF and water, dry the organic layer over MgSO4, and concentrate. After separation using a silica gel column and recrystallization, 10.6 g of the product (yield: 82%) was obtained.

[0182] 2. Sub1-7 Synthesis Example

[0183]

[0184] 1-bromo-4-(tert-butyl)-2-iodobenzene (16.9 g, 50.0 mmol), (4-(tert-butyl)phenyl)boronic acid (8.9 g, 50.0 mmol), Pd(PPh3)4 (1.73 g, 1.5 mmol), NaOH (6.0 g, 150 mmol), THF (120 mL), and water (40 mL) were added to a round-bottom flask, and the synthesis was carried out in the same manner as the synthesis method of Sub1-2 above, to obtain 13.6 g of the product (yield 79%).

[0185] 3. Sub1-11 Synthesis Example

[0186]

[0187] 6-(2-bromo-4-(tert-butyl)phenyl)-1-chlorodibenzo[b,d]furan (20.7 g, 50.0 mmol), (4-(tert-butyl)phenyl)boronic acid (8.9 g, 50.0 mmol), Pd(PPh3)4 (1.73 g, 1.5 mmol), NaOH (6.0 g, 150 mmol), THF (120 mL), and water (40 mL) were added to a round-bottom flask, and the synthesis was carried out in the same manner as the synthesis method of Sub1-2 above, obtaining 19.6 g of the product (yield 84%).

[0188] 4. Sub1-14 Synthesis Example

[0189]

[0190] 1-bromo-4-(tert-butyl)-2-chlorobenzene (12.9 g, 50.0 mmol), (3,5-di-tert-butylphenyl)boronic acid (11.7 g, 50.0 mmol), Pd(PPh3)4 (1.73 g, 1.5 mmol), NaOH (6.0 g, 150 mmol), THF (120 mL), and water (40 mL) were added to a round-bottom flask, and the synthesis was carried out in the same manner as the synthesis method of Sub1-2 above, obtaining 14.5 g of the product (yield 81%).

[0191] 5. Sub1-27 Synthesis Example

[0192]

[0193] 2-bromo-7-(2-bromo-5-(tert-butyl)phenyl)-9,9-dimethyl-9H-fluorene (24.2 g, 50.0 mmol), (4-(tert-butyl)phenyl)boronic acid (8.9 g, 50.0 mmol), Pd(PPh3)4 (1.73 g, 1.5 mmol), NaOH (6.0 g, 150 mmol), THF (120 mL), and water (40 mL) were added to a round-bottom flask, and the synthesis was carried out in the same manner as the synthesis method of Sub1-2 above, obtaining 15.6 g of the product (yield 58%).

[0194] 6. Sub1-28 Synthesis Example

[0195]

[0196] 2-bromo-7-(2-bromo-5-(tert-butyl)phenyl)-9,9-diphenyl-9H-fluorene (30.4 g, 50.0 mmol), (4-(tert-butyl)phenyl)boronic acid (8.9 g, 50.0 mmol), Pd(PPh3)4 (1.73 g, 1.5 mmol), NaOH (6.0 g, 150 mmol), THF (120 mL), and water (40 mL) were added to a round-bottom flask, and the synthesis was carried out in the same manner as the synthesis method of Sub1-2 above, obtaining 19.9 g of the product (yield 60%).

[0197] 7. Sub1-34 Synthesis Example

[0198]

[0199] 2-bromo-1-chloro-4-methylbenzene (10.3 g, 50.0 mmol), mesitylboronic acid (8.2 g, 50.0 mmol), Pd(PPh3)4 (1.73 g, 1.5 mmol), NaOH (6.0 g, 150 mmol), THF (120 mL), and water (40 mL) were added to a round-bottom flask, and the synthesis was performed in the same manner as the synthesis method of Sub1-2 above, obtaining 8.2 g of the product (yield 67%).

[0200] 8. Sub1-46 Synthesis Example

[0201]

[0202] 2-bromo-6-(2-bromo-4-(tert-butyl)phenyl)naphthalene (20.9 g, 50.0 mmol), (4-(tert-butyl)phenyl)boronic acid (8.9 g, 50.0 mmol), Pd(PPh3)4 (1.73 g, 1.5 mmol), NaOH (6.0 g, 150 mmol), THF (120 mL), and water (40 mL) were added to a round-bottom flask, and the synthesis was performed in the same manner as the synthesis method of Sub1-2 above, obtaining 13.0 g of the product (yield 55%).

[0203] Compounds belonging to Sub 1 may include, but are not limited to, the compounds below, and Table 1 shows the FD-MS (Field Desorption-Mass Spectrometry) values ​​of the compounds below.

[0204]

[0205]

[0206]

[0207]

[0208]

[0209]

[0210]

[0211]

[0212]

[0213]

[0214] 화합물FD-MS화합물FD-MSSub1-1m / z=284.13(C 19 H 21 Cl=284.83)Sub1-2m / z=258.12(C 17 H 19 Cl=258.79)Sub1-3m / z=298.15(C 20 H 23 Cl=298.85)Sub1-4m / z=286.84(C 19 H 23 Cl=286.84)Sub1-5m / z=326.18(C 22 H 27 Cl=326.91)Sub1-6m / z=338.18(C 23 H 27 Cl=338.92)Sub1-7m / z=344.11(C 20 H 25 Br=345.32)Sub1-8m / z=364.20(C 25 H 29 Cl=364.96)Sub1-9m / z=302.07(C 17 H 19 Br=303.24)Sub1-10m / z=392.10(C 20 H 25 I=392.32)Sub1-11m / z=466.21(C 32 H 31 ClO=467.05)Sub1-12m / z=352.20(C 24 H 29 Cl=352.95)Sub1-13m / z=307.21(C 20 H 18 D7Cl=307.91)Sub1-14m / z=356.23(C 24 H 33Cl=356.98)Sub1-15m / z=298.15(C 20 H 23 Cl=298.85)Sub1-16m / z=318.16(C 20 H 24 ClF=318.86)Sub1-17m / z=392.10(C 20 H 25 I=392.32)Sub1-18m / z=408.26(C 28 H 37 Cl=409.05)Sub1-19m / z=376.20(C 26 H 29 Cl=376.97)Sub1-20m / z=352.20(C 24 H 29 Cl=352.95)Sub1-21m / z=444.22(C 30 H 33 ClO=445.04)Sub1-22m / z=286.15(C 19 H 23 Cl=286.84)Sub1-23m / z=335.14(C 22 H 22 ClN=335.87)Sub1-24m / z=610.25(C 42 H 39 ClS=611.28)Sub1-25m / z=504.26(C 36 H 37 Cl=505.14)Sub1-26m / z=518.24(C 36 H 35 ClO=519.13)Sub1-27m / z=536.21(C 35 H 37 Br=537.59)Sub1-28m / z=660.24(C 45 H 41 Br=661.73)Sub1-29m / z=526.13(C 32 H 31 BrS=527.56)Sub1-30m / z=260.02(C 14 H 13 Br=261.16)Sub1-31m / z=258.12(C 17 H 19 Cl=258.79)Sub1-32m / z=376.20(C 26 H29 Cl=376.97)Sub1-33m / z=482.18(C 32 H 31 ClS=483.11)Sub1-34m / z=244.10(C 16 H 17 Cl=244.76)Sub1-35m / z=500.21(C 32 H 37 Br=501.55)Sub1-36m / z=424.16(C 29 H 2% ClO=424.97)Sub1-37m / z=230.09(C 15 H 15 Cl=230.74)Sub1-38m / z=258.12(C 17 H 19 Cl=258.79)Sub1-39m / z=548.19(C 39 H 29 ClO=549.11)Sub1-40m / z=562.17(C 39 H 27 ClO2=563.09)Sub1-41m / z=368.13(C 26 H 21 Cl=368.90)Sub1-42m / z=458.18(C 33 H 27 Cl=459.03)Sub1-43m / z=514.13(C 34 H 27 Br=515.49)Sub1-44m / z=488.14(C 33 H 25 ClS=489.07)Sub1-45m / z=307.21(C 20 H 18 D7Cl=307.91)Sub1-46m / z=470.16(C 30 H 31 Br=471.48)Sub1-47m / z=426.21(C 30 H 31 Cl=427.03)Sub1-48m / z=404.23(C 28 H 33 Cl=405.02)Sub1-49m / z=258.12(C 17 H 19 Cl=258.79)Sub1-50m / z=482.18(C32 H 31 ClS=483.11)Sub1-51m / z=528.26(C 38 H 37 Cl=529.16)Sub1-52m / z=542.24(C 38 H 35 ClO=543.15)Sub1-53m / z=614.27(C 45 H 39 Cl=615.26)Sub1-54m / z=482.18(C 32 H 31 ClS=483.11Sub1-55m / z=492.26(C 35 H 37 Cl=493.13)Sub1-56m / z=492.26(C 35 H 37 Cl=493.13)

[0215] Synthesis example of Sub 2

[0216] Sub 2 of the above reaction scheme 1 can be synthesized by the reaction path of the following reaction scheme 3, but is not limited thereto.

[0217] <Reaction Scheme 3> (Hal 4 is I, Br or Cl)

[0218]

[0219] 1. Sub2-1 Synthesis Example

[0220]

[0221] In a round-bottomed flask, 9,9-dimethyl-9H-fluoren-1-amine (10.5 g, 50.0 mmol), 1-bromo-4-cyclohexylbenzene (12.0 g, 50.0 mmol), Pd2(dba)3 (1.4 g, 1.5 mmol), P(t-Bu)3 (0.6 g, 3.0 mmol), NaOt-Bu (10.6 g, 110 mmol), and toluene (170 mL) were added and stirred at 60 °C. Upon completion of the reaction, the mixture was extracted with toluene and water, and the organic layer was dried over MgSO4 and concentrated. Afterwards, the product was separated using a silica gel column and recrystallized to obtain 15.4 g (yield: 84%).

[0222] 2. Sub2-5 Synthesis Example

[0223]

[0224] 9,9-dimethyl-9H-fluoren-2-amine (10.5 g, 50.0 mmol), 1-(4-bromophenyl)adamantane (14.6 g, 50.0 mmol), Pd2(dba)3 (1.4 g, 1.5 mmol), P(t-Bu)3 (0.6 g, 3.0 mmol), NaOt-Bu (10.6 g, 110 mmol), and toluene (170 mL) were added to a round-bottom flask, and the synthesis was performed in the same manner as the synthesis example of Sub2-1 above, obtaining 18.3 g of the product (yield 87%).

[0225] 3. Sub2-17 Synthesis Example

[0226]

[0227] 5-(dibenzo[b,d]furan-3-yl)-9,9-dimethyl-9H-fluoren-2-amine (18.8 g, 50.0 mmol), 1-bromo-4-cyclohexylbenzene (12.0 g, 50.0 mmol), Pd2(dba)3 (1.4 g, 1.5 mmol), P(t-Bu)3 (0.6 g, 3.0 mmol), NaOt-Bu (10.6 g, 110 mmol), and toluene (170 mL) were added to a round-bottom flask, and the synthesis was performed in the same manner as the synthesis example of Sub2-1 above, obtaining 22.1 g of the product (yield 83%).

[0228] 4. Sub2-25 Synthesis Example

[0229]

[0230] 5,5-dimethyl-5H-dibenzo[b,d]silol-3-amine (11.3 g, 50.0 mmol), 1-bromo-4-cyclohexylbenzene (12.0 g, 50.0 mmol), Pd2(dba)3 (1.4 g, 1.5 mmol), P(t-Bu)3 (0.6 g, 3.0 mmol), NaOt-Bu (10.6 g, 110 mmol), and toluene (170 mL) were added to a round-bottom flask, and the synthesis was carried out in the same manner as the synthesis example of Sub2-1 above, obtaining 14.8 g of the product (yield 77%).

[0231] 5. Sub2-38 Synthesis Example

[0232]

[0233] 9-methyldibenzo[b,d]furan-3-amine (9.9 g, 50.0 mmol), 4'-bromo-2-cyclohexyl-1,1'-biphenyl (15.8 g, 50.0 mmol), Pd2(dba)3 (1.4 g, 1.5 mmol), P(t-Bu)3 (0.6 g, 3.0 mmol), NaOt-Bu (10.6 g, 110 mmol), and toluene (170 mL) were added to a round-bottom flask, and the synthesis was carried out in the same manner as the synthesis example of Sub2-1 above, obtaining 16.2 g of the product (yield 75%).

[0234] 6. Sub2-48 Synthesis Example

[0235]

[0236] Dibenzo[b,d]furan-2-amine (9.2 g, 50.0 mmol), 1-bromo-4-cyclohexylbenzene (12.0 g, 50.0 mmol), Pd2(dba)3 (1.4 g, 1.5 mmol), P(t-Bu)3 (0.6 g, 3.0 mmol), NaOt-Bu (10.6 g, 110 mmol), and toluene (170 mL) were added to a round-bottom flask, and the synthesis was carried out in the same manner as the synthesis example of Sub2-1 above, obtaining 14.9 g of the product (yield 87%).

[0237] 7. Sub2-54 Synthesis Example

[0238]

[0239] Dibenzo[b,d]thiophen-2-amine (10.0 g, 50.0 mmol), 2-(4-bromophenyl)bicyclo[2.2.1]heptane (12.6 g, 50.0 mmol), Pd2(dba)3 (1.4 g, 1.5 mmol), P(t-Bu)3 (0.6 g, 3.0 mmol), NaOt-Bu (10.6 g, 110 mmol), and toluene (170 mL) were added to a round-bottom flask, and the synthesis was carried out in the same manner as the synthesis example of Sub2-1 above, obtaining 16.4 g of the product (yield 89%).

[0240] 8. Sub2-64 synthesis example

[0241]

[0242] Dibenzo[b,d]thiophen-1-amine (10.0 g, 50.0 mmol), 2-bromo-5-cyclohexyl-9,9-dimethyl-9H-fluorene (17.8 g, 50.0 mmol), Pd2(dba)3 (1.4 g, 1.5 mmol), P(t-Bu)3 (0.6 g, 3.0 mmol), NaOt-Bu (10.6 g, 110 mmol), and toluene (170 mL) were added to a round-bottom flask, and the synthesis was carried out in the same manner as the synthesis example of Sub2-1 above, obtaining 21.8 g of the product (yield 92%).

[0243] Compounds belonging to Sub 2 may include, but are not limited to, the compounds below, and the FD-MS values ​​of the compounds below are as shown in Table 2 below.

[0244]

[0245]

[0246]

[0247]

[0248]

[0249]

[0250]

[0251]

[0252]

[0253]

[0254]

[0255]

[0256]

[0257]

[0258]

[0259]

[0260]

[0261] 화합물FD-MS화합물FD-MSSub2-1m / z=367.23(C 27 H 29 N=367.54)Sub2-2m / z=379.23(C 28 H 29 N=379.55)Sub2-3m / z=419.26(C 31 H 33 N=419.61)Sub2-4m / z=353.21(C 26 H 27 N=353.51)Sub2-5m / z=419.26(C 31 H 33 N=419.61)Sub2-6m / z=367.23(C 27 H 29 N=367.54)Sub2-7m / z=415.23(C 31 H 29 N=415.58)Sub2-8m / z=492.26(C 36 H 32 N=492.67)Sub2-9m / z=469.24(C 34 H 31NO=469.63)Sub2-10m / z=443.26(C 33 H 33 N=443.63)Sub2-11m / z=443.26(C 33 H 33 N=443.63)Sub2-12m / z=565.28(C 43 H 35 N=565.76)Sub2-13m / z=549.25(C 39 H 35 NS=549.78)Sub2-14m / z=367.23(C 27 H 29 N=367.54)Sub2-15m / z=449.30(C 33 H 27 D6N=449.67)Sub2-16m / z=459.29(C 34 H 37 N=459.68)Sub2-17m / z=533.27(C 39 H 35 NO=533.71)Sub2-18m / z=656.42(C 49 H 44 D5N=656.97)Sub2-19m / z=549.25(C 39 H 35 NS=549.78)Sub2-20m / z=395.26(C 29 H 33 N=395.59)Sub2-21m / z=625.28(C 45 H 39 NS=625.87)Sub2-22m / z=495.29(C 37 H 37 N=495.71)Sub2-23m / z=495.29(C 37 H 37 N=495.71)Sub2-24m / z=587.369(C 44 H 45 N=587.85)Sub2-25m / z=383.21(C 26 H 29 NSi=383.61)Sub2-26m / z=507.24(C 36 H 33 NSi=507.75)Sub2-27m / z=439.27(C 30 H37 NSi=439.72)Sub2-28m / z=535.27(C 38 H 37 NSi=535.81)Sub2-29m / z=465.29(C 32 H 39 NSi=465.76)Sub2-30m / z=395.21(C 27 H 29 NSi=395.62)Sub2-31m / z=563.26(C 39 H 37 NOSi=563.82)Sub2-32m / z=387.23(C 26 H 25 D4NSi=387.63)Sub2-33m / z=458.22(C 31 H 30 N2Si=485.68)Sub2-34m / z=433.22(C 30 H 31 NSi=433.67)Sub2-35m / z=433.22(C 30 H 31 NSi=433.67)Sub2-36m / z=433.22(C 30 H 31 NSi=433.67)Sub2-37m / z=483.24(C 34 H 33 NSi=483.73)Sub2-38m / z=431.22(C 31 H 29 NO=431.58)Sub2-39m / z=493.24(C 36 H 31 NO=493.65)Sub2-40m / z=429.21(C 31 H 27 NO=429.56)Sub2-41m / z=409.24(C 29 H 31 NO=409.57)Sub2-42m / z=409.17(C 25 H 22 F3NO=409.45)Sub2-43m / z=413.22(C 27 H 31 NOSi=413.64)Sub2-44m / z=393.21(C 28 H 27NO=393.53)Sub2-45m / z=393.21(C 28 H 27 NO=393.53)Sub2-46m / z=418.20(C 29 H 26 N2O=418.54)Sub2-47m / z=507.22(C 36 H 29 NO2=507.63)Sub2-48m / z=341.18(C 24 H 23 NO=341.45)Sub2-49m / z=348.22(C 24 H 16 D7NO=348.50)Sub2-50m / z=403.19(C 29 H 25 NO=403.52)Sub2-51m / z=403.19(C 29 H 25 NO=403.52)Sub2-52m / z=459.17(C 31 H 25 NOS=459.61)Sub2-53m / z=459.17(C 31 H 25 NOS=459.61)Sub2-54m / z=369.16(C 25 H 23 NS=369.53)Sub2-55m / z=545.22(C 39 H 31 NS=545.74)Sub2-56m / z=369.16(C 25 H 23 NS=369.53)Sub2-57m / z=369.16(C 25 H 23 NS=369.53)Sub2-58m / z=522.21(C 36 H 30 N2S=522.71)Sub2-59m / z=611.23(C 43 H 33 NOS=611.80)Sub2-60m / z=383.17(C 26 H 25 NS=383.55)Sub2-61m / z=733.19(C 49 H 35 NS3=734.01)Sub2-62m / z=463.14(C 30H 25 NS2=463.66)Sub2-63m / z=357.16(C 24 H 23 NS=357.52)Sub2-64m / z=473.22(C 33 H 31 NS=473.68)Sub2-65m / z=407.17(C 28 H 25 NS=407.57)Sub2-66m / z=407.17(C 28 H 25 NS=407.57)Sub2-67m / z=457.19(C 32 H 27 NS=457.63)Sub2-68m / z=473.18(C 32 H 27 NOS=473.63)

[0262] Synthesis example of the final compound

[0263] 1. P1-1 Synthesis Example

[0264]

[0265] In a round-bottomed flask, add Sub1-1 (7.1 g, 25.0 mmol), Sub2-1 (9.2 g, 25.0 mmol), Pd2(dba)3 (0.7 g, 0.75 mmol), P(t-Bu)3 (0.3 g, 1.5 mmol), NaOt-Bu (5.3 g, 55 mmol), and toluene (85 mL), and stir at 130°C. Upon completion of the reaction, extract with toluene and water, dry the organic layer over MgSO4, and concentrate. The concentrate was then separated through a silica gel column and recrystallized to obtain 11.2 g of the product (yield: 73%).

[0266] 2. P1-10 Synthesis Example

[0267]

[0268] Sub1-9 (7.6 g, 25.0 mmol), Sub2-7 (10.4 g, 25.0 mmol), Pd2(dba)3 (0.7 g, 0.75 mmol), P(t-Bu)3 (0.3 g, 1.5 mmol), NaOt-Bu (5.3 g, 55 mmol), and toluene (85 mL) were added to a round-bottom flask, and the synthesis was carried out in the same manner as the synthesis example of P1-1, obtaining 11.3 g of the product (yield 71%).

[0269] 3. P2-5 Synthesis Example

[0270]

[0271] Sub1-20 (8.8 g, 25.0 mmol), Sub2-29 (11.6 g, 25.0 mmol), Pd2(dba)3 (0.7 g, 0.75 mmol), P(t-Bu)3 (0.3 g, 1.5 mmol), NaOt-Bu (5.3 g, 55 mmol), and toluene (85 mL) were added to a round-bottom flask, and the synthesis was carried out in the same manner as the synthesis example of P1-1, obtaining 15.1 g of the product (yield 77%).

[0272] 4. P2-17 Synthesis Example

[0273]

[0274] Sub1-30 (6.5 g, 25.0 mmol), Sub2-34 (10.8 g, 25.0 mmol), Pd2(dba)3 (0.7 g, 0.75 mmol), P(t-Bu)3 (0.3 g, 1.5 mmol), NaOt-Bu (5.3 g, 55 mmol), and toluene (85 mL) were added to a round-bottom flask, and the synthesis was carried out in the same manner as the synthesis example of P1-1, obtaining 12.4 g of the product (yield 81%).

[0275] 5. P3-3 Synthesis Example

[0276]

[0277] Sub1-32 (9.4 g, 25.0 mmol), Sub2-40 (10.7 g, 25.0 mmol), Pd2(dba)3 (0.7 g, 0.75 mmol), P(t-Bu)3 (0.3 g, 1.5 mmol), NaOt-Bu (5.3 g, 55 mmol), and toluene (85 mL) were added to a round-bottom flask, and the synthesis was performed in the same manner as in the synthesis example of P1-1, obtaining 14.6 g of the product (yield 76%).

[0278] 6. P3-14 Synthesis Example

[0279]

[0280] Sub1-42 (11.5 g, 25.0 mmol), Sub2-48 (8.5 g, 25.0 mmol), Pd2(dba)3 (0.7 g, 0.75 mmol), P(t-Bu)3 (0.3 g, 1.5 mmol), NaOt-Bu (5.3 g, 55 mmol), and toluene (85 mL) were added to a round-bottom flask, and the synthesis was carried out in the same manner as the synthesis example of P1-1 above, obtaining 16.6 g of the product (yield 87%).

[0281] 7. P4-2 Synthesis Example

[0282]

[0283] Sub1-10 (9.8 g, 25.0 mmol), Sub2-55 (13.6 g, 25.0 mmol), Pd2(dba)3 (0.7 g, 0.75 mmol), P(t-Bu)3 (0.3 g, 1.5 mmol), NaOt-Bu (5.3 g, 55 mmol), and toluene (85 mL) were added to a round-bottom flask, and the synthesis was carried out in the same manner as the synthesis example of P1-1, obtaining 16.2 g of the product (yield 80%).

[0284] 8. P4-13 Synthesis Example

[0285]

[0286] Sub1-54 (12.1 g, 25.0 mmol), Sub2-62 (11.6 g, 25.0 mmol), Pd2(dba)3 (0.7 g, 0.75 mmol), P(t-Bu)3 (0.3 g, 1.5 mmol), NaOt-Bu (5.3 g, 55 mmol), and toluene (85 mL) were added to a round-bottom flask, and the synthesis was carried out in the same manner as the synthesis example of P1-1 above, obtaining 20.0 g of the product (yield 88%).

[0287] 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.

[0288] Compound FD-MS Compound FD-MSP1-1 m / z = 615.39 (C 46 H 49 N=615.90)P1-2m / z=(C 45 H 47 N=601.88)P1-3m / z=681.43(C 51 H 55 N=682.01)P1-4m / z=603.39(C 45 H 49 N=603.89)P1-5m / z=669.43(C 50 H 55 N=670.00)P1-6m / z=681.43(C 51 H 55 N=682.01)P1-7m / z=683.45(C 51 H 57 N=684.02)P1-8m / z=747.48(C 56 H 61 N=748.11)P1-9m / z=589.37(C 44 H 47 N=589.87)P1-10m / z=637.37(C 48 H 47 N=637.91)P1-11m / z=714.40(C 53 H 50 N2=715.00)P1-12m / z=691.38(C 51 H 49 NO=691.96)P1-13m / z=707.45(C 53 H57 N=708.05)P1-14m / z=707.45(C 53 H 57 N=708.05)P1-15m / z=829.46(C 63 H 59 N=830.17)P1-16m / z=771.39(C 56 H 53 NS=772.11)P1-17m / z=797.46(C 59 H 59 NO=798.13)P1-18m / z=765.52(C 57 H 55 D6N=766.16)P1-19m / z=6383.46(C 47 H 46 D7N=638.99)P1-20m / z=779.54(C 58 H 69 N=780.20)P1-21m / z=809.46(C 60 H 59 NO=810.14)P1-22m / z=938.60(C 69 H 67 D5FN=939.37)P1-23m / z=813.44(C 59 H 59 NS=814.19)P1-24m / z=759.48(C 57 H 61 N=760.12)P1-25m / z=889.47(C 65 H 63 NS=890.29)P1-26m / z=759.48(C 57 H 61 N=760.12)P1-27m / z=759.48(C 57 H 61 N=760.12)P1-28m / z=851.54(C 64 H 69 N=852.26)P2-1m / z=647.39(C 46 H 53 NSi=648.02)P2-2m / z=771.43(C 56 H 57 NSi=772.16)P2-3m / z=811.55(C 58 H 73NSi=812.31)P2-4m / z=875.49(C 64 H 65 NSi=876.32)P2-5m / z=781.50(C 56 H 67 NSi=782.24)P2-6m / z=791.45(C 56 H 61 NSi=792.20)P2-7m / z=633.38(C 45 H 51 NSi=634.00)P2-8m / z=694.37(C 49 H 50 N2Si=695.04)P2-9m / z=879.48(C 63 H 65 NOSi=880.30)P2-10m / z=957.48(C 68 H 667 NSSi=958.44)P2-11m / z=855.51(C 62 H 61 D4NSi=856.32)P2-12m / z=865.47(C 62 H 63 NOSi=866.28)P2-13m / z=839.49(C 61 H 65 NSi=840.28)P2-14m / z=963.52(C 71 H 69 NSi=964.42)P2-15m / z=829.41(C 58 H 59 NSSi=830.26)P2-16m / z=638.31(C 45 H 42 N2Si=638.93)P2-17m / z=613.32(C 44 H 43 NSi=613.92)P2-18m / z=613.32(C 44 H 43 NSi=613.92)P2-19m / z=613.32(C 44 H 43 NSi=613.92)P2-20m / z=663.33(C 48 H 45 NSi=663.98)P3-1m / z=653.37(C 48 H 47NO=653.91)P3-2m / z=833.46(C 62 H 59 NO=834.16)P3-3m / z=769.43(C 57 H 55 NO=770.07)P3-4m / z=855.45(C 61 H 61 NOS=856.22)P3-5m / z=617.29(C 41 H 38 F3NO=617.76)P3-6m / z=621.34(C43H 47 NOSi=621.94)P3-7m / z=813.49(C 60 H 63 NO=814.17)P3-8m / z=781.39(C 57 H 52 NO2=782.04)P3-9m / z=612.31(C 44 H 40 N2O=612.82)P3-10m / z=729.36(C 53 H 47 NO2=729.96)P3-11m / z=853.39(C 63 H 51 NO2=854.11)P3-12m / z=867.37(C 63 H 49 NO3=868.09)P3-13m / z=680.38(C 50 H 36 D7NO=680.94)P3-14m / z=763.38(C 57 H 49 NO=764.02)P3-15m / z=775.38(C 58 H 49 NO=776.04)P3-16m / z=793.34(C 57 H 47 NOS=794.07)P3-17m / z=667.38(C 49 H 49 NO=667.94)P3-18m / z=667.38(C 49 H 49 NO=667.94)P3-19m / z=723.35(C 51 H 49 NOS=724.02)P3-20m / z=723.35(C51 H 49 NOS=724.02)P4-1m / z=640.39(C 45 H 40 D7NS=640.98)P4-2m / z=809.41(C 59 H 55 NS=810.16)P4-3m / z=759.39(C 55 H 53 NS=760.10)P4-4m / z=760.10(C 55 H 53 NS=760.10)P4-5m / z=786.40(C 56 H 54 N2S=787.12)P4-6m / z=875.42(C 63 H 57 NOS=876.21)P4-7m / z=737.41(C 53 H 55 NS=738.09)P4-8m / z=605.31(C 43 H 45 NS=605.88)P4-9m / z=1179.40(C 81 H 65 NS4=1180.66)P4-10m / z=861.44(C 63 H 59 NS=862.23)P4-11m / z=875.42(C 63 H 57 NOS=876.21)P4-12m / z=947.45(C 70 H 61 NS=948.33)P4-13m / z=909.35(C 62 H 55 NS3=910.31)P4-14m / z=919.42(C 65 H 61 NS2=920.33)P4-15m / z=813.44(C 59 H 59 NS=814.19)P4-16m / z=929.50(C 68 H 67 NS=930.35)P4-17m / z=671.36(C 48 H 49 NS=671.99)P4-18m / z=671.36(C 48 H 49NS=671.99)P4-19m / z=721.37(C 52 H 51 NS=722.05)P4-20m / z=737.37(C 52 H 51 NOS=738.05)

[0289] Although the above-described exemplary synthetic examples of the present invention represented by Chemical Formula 1 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), it will be readily understood by those skilled in the art that the above-described reaction proceeds even if a substituent other than the substituent specified in the specific synthetic example is combined with another substituent defined in Chemical Formula 1.

[0290] Manufacturing and evaluation of organic electronic devices

[0291] [Example 1] Red organic light-emitting device (luminescent auxiliary layer)

[0292] A hole injection layer was formed by vacuum-depositing 4,4',4"-tris[2-naphthyl(phenyl)amino]triphenylamine (hereinafter abbreviated as 2-TNATA) to a thickness of 60 nm on an ITO layer (anode) formed on a glass substrate, and then N,N'-bis(1-naphthalenyl)-N,N'-bis-phenyl-(1,1'-biphenyl)-4,4'-diamine (hereinafter abbreviated as NPB) was vacuum-deposited to a thickness of 60 nm on the hole injection layer to form a hole transport layer.

[0293] Afterwards, the compound P1-7 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.

[0294] Next, on the light-emitting auxiliary layer, 4,4'-N,N'-dicarbazole-biphenyl (hereinafter, CBP) was used as a host material, and bis-(1-phenylisoquinolyl)iridium(Ⅲ)acetylacetonate (hereinafter, abbreviated as '(piq)2Ir(acac)') was used as a dopant, and the dopant was doped so that the weight ratio of the host and the dopant was 95:5, thereby forming a light-emitting layer having a thickness of 30 nm.

[0295] Next, (1,1'-biphenyl-4-olato)bis(2-methyl-8-quinolinolato)aluminum (hereinafter abbreviated as BAlq) was vacuum-deposited to a thickness of 10 nm on the light-emitting layer to form a hole-blocking layer, and Tris(8-hydroxyquinolinato)aluminum (hereinafter abbreviated as Alq3) was vacuum-deposited to a thickness of 40 nm on the hole-blocking layer to form an electron transport layer.

[0296] Afterwards, 8-quinolinolato lithium (hereinafter abbreviated as Liq) was vacuum-deposited to a thickness of 0.2 nm on the electron transport layer to form an electron injection layer, and Al was deposited to a thickness of 150 nm on the electron injection layer to form a cathode.

[0297] [Example 2] to [Example 19]

[0298] 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 P1-7 of the present invention as a light-emitting auxiliary layer material.

[0299] [Comparative Example 1] to [Comparative Example 3]

[0300] An organic light-emitting device was manufactured in the same manner as Example 1, except that one of the following comparative compounds A to C was used instead of the compound P1-7 of the present invention as the light-emitting auxiliary layer material.

[0301] Comparative Compound A Comparative Compound B Comparative Compound C

[0302]

[0303] The electroluminescence (EL) characteristics were measured by applying a forward bias DC voltage to the organic electroluminescence devices manufactured by the examples and comparative examples of the present invention using a PR-650 from Photoresearch, and 2,500 cd / m 2 The T95 lifespan was measured using a lifespan measuring device manufactured by Maxscience at a reference luminance. The measurement results are shown in Table 4 below.

[0304] 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.

[0305] Compound driving voltage (V) Current density (mA / cm) 2 ) Luminance (cd / m 2)Efficiency (cd / A)Lifetime T (95)Comparative Example (1)Comparative Compound A5.115.72500.015.983.6Comparative Example (2)Comparative Compound B5.313.82500.018.190.3Comparative Example (3)Comparative Compound C5.414.52500.017.391.6Embodiment (1)P1-74.89.92500.025.3119.6Embodiment (2)P1-154.910.82500.023.1116.2Embodiment (3)P1-165.011.02500.022.7108.0Embodiment (4)P1-244.810.02500.024.9118.3Embodiment (5)P1-2 64.910.72500.023.3115.5 Example (6) P1-274.910.42500.024.0113.6 Example (7) P1-284.910.22500.024.5116.4 Example (8) P2-14.911.12500.022.6114.8 Example (9) P2-24.911.02500.022.7114.3 Example (10) P2- 155.011.92500.021.0108.1 Example (11) P2-174.911.22500.022.3113.4 Example (12) P3-45.010.92500.022.9104.3 Example (13) P3-105.011.82500.021.1110.0 Example (14) P3-174.911.82500.021.2112.7 Example ( 15)P3-194.911.02500.022.7109.2Example (16)P4-14.911.12500.022.6107.5Example (17)P4-25.011.42500.022.0106.3Example (18)P4-74.911.12500.022.6105.7Example (19)P4-175.011.82500.021.2104.6

[0306] From the above Table 4, it can be seen that when the compound of the present invention is used as a light-emitting auxiliary layer material, the driving voltage of the organic light-emitting device is lowered and the efficiency and lifespan are significantly improved compared to when one of the comparative compounds A to C is used. Comparative compounds A to C are similar to the compound in which X is C(R1)(R2) in the chemical formula 1 of the present invention in that they are tertiary amine structures in which a 3-condensed ring such as a fluorenyl group is substituted, but comparative compounds B and C are similar to the compound in which X is C(R1)(R2) in the chemical formula 1 of the present invention in that comparative compound A does not contain a substituent corresponding to the chemical formula A of the present invention. 1 It differs in that it does not contain an aliphatic ring group as a corresponding substituent.

[0307] First, we examine the effect of substitution of aliphatic ring groups in the compound.

[0308] In order to confirm the dipole moment of the compound according to the presence or absence of aliphatic ring substitution, the compound of the present invention, which has a high similarity to comparative compounds B and C, was measured using the DFT method (B3LYP / 6-31g(D)) of the Gaussian program. The measurement results are shown in Table 5 below.

[0309] Comparative Compound BP1-27 Comparative Compound CP1-28 Dipole moment (D) 1.1660 1.2649 1.205 11.2955

[0310] From the above Table 5, it can be seen that the dipole moment of the compound of the present invention is much larger than that of the comparative compound B or the comparative compound C. That is, the compound of the present invention containing an aliphatic ring group has a larger dipole moment value than the comparative compound. Therefore, it appears that the intramolecular van der Waals interaction of the compound of the present invention acts stronger than that of the comparative compound, thereby improving hole mobility when applied to an organic electric device, thereby improving charge balance within the light-emitting layer, and thus significantly improving the performance of the device.

[0311] Next, we examine the effect depending on whether the compound contains chemical formula A.

[0312] The compound of the present invention containing a moiety represented by the formula A has a lower Tg value than the comparative compound A that does not contain it, because the compound of the present invention containing the formula A, i.e., the o-biphenyl moiety, is structurally more twisted.

[0313] As a result, in the process of forming a light-emitting auxiliary layer, the compound of the present invention is deposited better than the comparative compound A even at a relatively low temperature, so the lifespan of the device appears to have improved.

[0314] Therefore, it can be seen that the organic light emitting device using the compound of the present invention, which is a tertiary amine structure containing a 3-condensed ring moiety, a moiety represented by chemical formula A, and an aliphatic ring group, as a light emitting auxiliary layer material has a remarkable effect compared to the case where one of comparative compounds A to C is used.

[0315] These results suggest that even for similar compounds, the properties of the compound, such as hole movement and injection characteristics, light efficiency characteristics, energy level, charge balance between holes and electrons, overall density, and intermolecular distance, may differ depending on the type and position of the substituted substituent, and that the properties of the device may differ significantly depending on these complex factors.

[0316] Therefore, in the case of the light-emitting auxiliary layer, the relationship between the hole transport layer and the light-emitting layer (host) must be understood, and even if a similar core is used, it would be very difficult for even a person skilled in the art to infer the remarkable effect exhibited in the light-emitting auxiliary layer using the compound of the present invention.

[0317] In addition, 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 may be applied to both the hole transport layer and the light-emitting auxiliary layer.

[0318] 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, A is chemical formula A, X is O, S, C(R1)(R2) or Si(R3)(R4) Ar 1 Silver C6~C 60 C2~C containing an arylene group or at least one heteroatom among O, N, S, Si and P 60 is a heterocyclic group, Ak 1 is C3~C 60 It is a fatty acid ring, Ak 2 and Ak 3 are independently of each other C1~C 20 Alkyl group or C3~C 60 It is a fatty acid ring, R 1 Inland R 4 are independently hydrogen; deuterium; halogen; cyano group; nitro 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 R 1 R in pairs or neighboring pairs 2 They can combine with each other to form rings, a and d are integers from 0 to 4, b and c are integers from 0 to 3, R1 to R4 are independently 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 combine with each other to form a ring, L 1 Inland L 3 are independently of each other and are single bonds; C6~C 60 C2~C containing an arylene group of; and at least one heteroatom of O, N, S, Si and P 60 is selected from the group consisting of heterocyclic groups, The above aryl group, arylene group, fluorenyl group, heterocyclic group, aliphatic ring group, fused ring group, alkyl group, alkenyl group, alkynyl group, alkoxy group, aryloxy group, and the ring formed by bonding adjacent groups to each other are each 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; nitro group; C1-C 20 Alkylthio group of; C1-C 20 Alkoxy group of; C6-C 30 Aryloxy group of; C6-C 30 Arylthio 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; 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.

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

3. In paragraph 1, The above chemical formula A is a compound characterized by being selected from the group consisting of the following chemical formulas A-1 to A-12: <Chemical Formula A-1> <Chemical Formula A-2> <Chemical Formula A-3> <Chemical Formula A-4> <Chemical Formula A-5> <Chemical Formula A-6> <Chemical Formula A-7> <Chemical Formula A-8> <Chemical Formula A-9> <Chemical Formula A-10> <Chemical Formula A-11> <Chemical Formula A-12> In the above chemical formulas A-1 to A-12, Ak 2 , Ak 3 , R 3 , R 4 , c, d are as defined in paragraph 1.

4. In paragraph 1, Ak 1 A compound characterized by being selected from the group consisting of the following chemical formulas 4-1 to 4-3: <Chemical Formula 4-1> <Chemical Formula 4-2> <Chemical Formula 4-3>.

5. In paragraph 1, Ak 2 and Ak 3 A compound characterized in that at least one of the compounds is selected from the group consisting of the following chemical formulae 5-1 to 5-7: <Chemical Formula 5-1> <Chemical Formula 5-2> <Chemical Formula 5-3> <Chemical Formula 5-4> <Chemical Formula 5-5> <Chemical Formula 5-6> <Chemical Formula 5-7> .

6. In paragraph 1, Ar 1 A compound characterized by being selected from the group consisting of the following chemical formulas Ar-1 to Ar-9: <Chemical formula Ar-1> <Chemical formula Ar-2> <Chemical formula Ar-3> <Chemical formula Ar-4> <Chemical formula Ar-5> <Chemical formula Ar-6> <Chemical formula Ar-7> <Chemical formula Ar-8> <Chemical formula Ar-9> In the above chemical formula, R 5 and R 6 are independently hydrogen, 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; nitro group; C1-C 20 Alkylthio group of; C1-C 20 Alkoxy group of; C6-C 30 Aryloxy group of; C6-C 30 Arylthio 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; 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 is selected from the group consisting of heterocyclic groups, and adjacent groups can combine with each other to form a ring, e and f are integers from 0 to 4, respectively.

7. In paragraph 1, A compound represented by the above chemical formula 1 is characterized in that it is one of the following compounds: .

8. 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 comprising the compound of claim 1, wherein the organic layer comprises:

9. In paragraph 8, An organic electric device wherein the organic layer includes a light-emitting layer between the first electrode and the second electrode and a light-emitting auxiliary layer between the first electrode and the light-emitting layer, and the light-emitting auxiliary layer includes the compound.

10. In paragraph 8, An organic electric device comprising two or more stacks including a hole transport layer, a light emitting layer, and an electron transport layer sequentially formed on the first electrode, wherein the organic layer comprises:

11. In paragraph 8, An organic electric device wherein the organic layer further includes a charge generation layer formed between two or more stacks.

12. In paragraph 8, The organic electric element further includes a light efficiency improvement layer, and the light efficiency improvement layer is formed on one surface of the first electrode or the second electrode that is not in contact with the organic layer.

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

14. In paragraph 13, The above organic electroluminescent device is an electronic device selected from the group consisting of an organic electroluminescent device, an organic solar cell, an organic photoconductor, an organic transistor, a monochrome lighting device, and a quantum dot display device.

15. 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.

16. In paragraph 15, A compound characterized in that the purity of the compound is 99.9% or higher.

17. A step of depositing an organic layer material including a compound represented by the chemical formula 1 of paragraph 1; A step of recovering the organic layer material attached to the deposition equipment; and A method for recovering a compound represented by the above chemical formula 1, characterized in that it comprises a step of purifying the recovered organic layer material to obtain a compound represented by the above chemical formula 1 having a purity of 99.9% or higher.

18. In paragraph 17, A method for recovering a compound represented by the above chemical formula 1, characterized in that the purification of the recovered organic layer material comprises 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.

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