KR20200017727A - Organic electronic element comprising mixture mixed with different compounds as host material and an electronic device thereof - Google Patents

Abstract

Provided are an organic electrical device using a mixture of a compound represented by chemical formula 1, a compound represented by chemical formula 2, and a compound represented by chemical formula 3 as a host material of a phosphorescent layer, and an electronic device thereof. According to the present invention, by using the mixture as a phosphorescent host material, a driving voltage of the organic electrical device can be lowered, and a light emitting efficiency and a lifespan of the organic electrical device can be increased.

Description

ORGANIC ELECTRONIC ELEMENT COMPRISING MIXTURE MIXED WITH DIFFERENT COMPOUNDS AS HOST MATERIAL AND AN ELECTRONIC DEVICE THEREOF}

The present invention relates to an organic electronic device and an electronic device thereof, and more particularly, to an organic electronic device and an electronic device having improved driving voltage, luminous efficiency and lifetime by using a mixture of heterogeneous compounds as a host material.

In general, organic light emitting phenomenon refers to a phenomenon of converting electrical energy into light energy using an organic material. An organic electric device using an organic light emitting phenomenon usually has a structure including an anode, a cathode, and an organic material layer therebetween. The organic layer is often made of a multi-layer structure composed of different materials in order to increase the efficiency and stability of the organic electrical device, for example, it may be made of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer.

Materials used as the organic material layer in the organic electric element may be classified into light emitting materials and charge transport materials such as hole injection materials, hole transport materials, electron transport materials, electron injection materials and the like according to their functions. The light emitting material may be classified into a polymer type and a low molecular type according to molecular weight, and may be classified into a fluorescent material derived from a singlet excited state of electrons and a phosphorescent material derived from a triplet excited state of electrons according to a light emitting mechanism. Can be. In addition, the light emitting materials may be classified into blue, green, and red light emitting materials and yellow and orange light emitting materials required to achieve better natural colors according to light emission colors.

On the other hand, when only one material is used as the light emitting material, the maximum light emission wavelength is shifted to the long wavelength due to the intermolecular interaction, and the color purity decreases or the efficiency of the device decreases due to the light emission attenuation effect. In order to increase the light emitting efficiency through the light emitting material, a host / dopant system may be used. The principle is that when a small amount of dopant having an energy band gap smaller than that of the host forming the light emitting layer is mixed in the light emitting layer, excitons generated in the light emitting layer are transported to the dopant, thereby producing high efficiency light. At this time, since the wavelength of the host is shifted to the wavelength of the dopant, light having a desired wavelength can be obtained according to the type of dopant to be used.

Currently, the portable display market is increasing in size with large-area displays, which requires more power consumption than that required in conventional portable displays. Therefore, power consumption has become a very important factor for a portable display having a limited power supply such as a battery, and a problem of efficiency and lifespan must also be solved.

Efficiency, lifespan, and driving voltage are related to each other.As the efficiency increases, the driving voltage decreases relatively, and the crystallization of organic materials due to Joule heating generated during driving decreases as the driving voltage decreases. It shows a tendency to increase the lifetime. However, simply improving the organic material layer does not maximize the efficiency. This is because a long life and high efficiency can be achieved at the same time when an optimal combination of energy level, T ₁ value, and intrinsic properties (mobility, interfacial properties, etc.) of each organic material layer is achieved. .

Therefore, development of a host material having high thermal stability and capable of achieving an efficient charge balance in the light emitting layer is required, and in particular, development of a phosphorescent host material is required.

Therefore, the present invention facilitates the HOMO level and LUMO level control of the phosphorescent host material by using a mixture containing three or more different compounds as the host material of the phosphorescent organic EL device, and thus charge balance in the light emitting layer. It is an object of the present invention to provide an organic electric element and its electronic device, which can improve) and thereby significantly improve driving voltage, efficiency and lifespan.

In one aspect, the present invention provides an organic electric device using a mixture containing a compound represented by each of the formulas (1) to (3) as a phosphorescent host material of the light emitting layer.

    <Formula 1> <Formula 2>

<Formula 3>

In another aspect, the present invention provides an electronic device including the organic electric element.

According to the present invention, by using a mixture of three or more different compounds as a phosphorescent host material to improve the hole / electronic control between the organic electroluminescent component layer, the driving voltage of the device can be lowered, luminous efficiency and lifetime Can improve.

1 is an exemplary view of an organic electroluminescent device according to the present invention.

As used herein, the terms "aryl group" and "arylene group" each have a carbon number of 6 to 60 unless otherwise stated, it is not limited thereto. In the present invention, the aryl group or arylene group includes monocyclic, ring aggregate, conjugated ring system, spiro compound and the like.

As used herein, the term "heterocyclic group" includes not only aromatic rings, such as "heteroaryl groups" or "heteroarylene groups," but also non-aromatic rings, and each carbon number includes one or more heteroatoms unless otherwise specified. It means a ring of 2 to 60, but is not limited thereto. As used herein, the term “heteroatom” refers to N, O, S, P, or Si unless otherwise indicated, and heterocyclic groups are monocyclic, ring aggregates, conjugated multiple ring systems, spies, including heteroatoms. Means a compound or the like.

As used herein, the term "heterocyclic group" means a ring containing a heteroatom such as N, O, S, P, or Si, instead of the carbon forming the ring, "heteroaryl group" or "heteroarylene group" In addition to the aromatic ring, such as a non-aromatic ring, and may include a compound containing a heteroatom such as SO ₂ , P = O and the like instead of the carbon forming the ring.

As used herein, the term "fluorenyl group" or "fluorenylene group" means a monovalent or divalent functional group in which R, R 'and R "are all hydrogen in the following structures, unless otherwise stated, and" Substituted fluorenyl group "or" substituted fluorenylene group "means that at least one of the substituents R, R ', and R" is a substituent other than hydrogen, and R and R' are bonded to each other to form a carbon It includes the case of forming a compound by spying together.

As used herein, the term "spiro compound" has a "spiro union", and a spiro linkage refers to a linkage formed by two rings sharing only one atom. In this case, the atoms shared by the two rings are called spiro atoms, and according to the number of spiro atoms in one compound, these are respectively referred to as 'monospyro-', 'diespyro-', 'trispyro-' 'Compound.

In the present specification, the 'group name' corresponding to the aryl group, arylene group, heterocyclic group, etc., which are illustrated as examples of each symbol and substituents thereof may describe 'the name of the group reflecting the singer', but may be described as 'the parent compound name'. You may. For example, in the case of phenanthrene, which is an aryl group, the monovalent `` group '' is phenanthryl and the divalent group may be described with the name of the group by dividing the mantissa, such as phenanthryl. Regardless, it may be described as the parent compound name 'phenanthrene'. Similarly, in the case of pyrimidine, it may be described as 'pyrimidine' irrespective of the valence, or as the 'name of the group' of the singer, such as pyrimidinyl group in the case of monovalent and pyrimidinylene in the case of divalent. have.

In addition, unless otherwise stated, the formulas used in the present invention apply equally to the substituent definitions based on the exponential definitions of the following formulas.

Herein, when a is an integer of 0, the substituent R ¹ is absent, when a is an integer of 1, one substituent R ¹ is bonded to any one of carbons forming the benzene ring, and a is an integer of 2 or 3 Each combine as follows, where R ¹ may be the same or different. When a is an integer of 4 to 6, it is bonded to the carbon of the benzene ring in a similar manner. In addition, the indication of the hydrogen couple | bonded with the carbon which forms the benzene ring can be abbreviate | omitted.

Hereinafter, a lamination structure of an organic electric device including the compound of the present invention will be described with reference to FIG. 1.

 In describing the present invention, when it is determined that the detailed description of the related well-known configuration or function may obscure the gist of the present invention, the detailed description thereof will be omitted. In addition, if a component such as a layer, film, region, plate, etc. is said to be "on" or "on" another component, it is not only when the other component is "right on" but also another component in between It is to be understood that this may also include cases. Conversely, if a component is said to be "directly above" another part, it should be understood to mean that there is no other part in the middle.

1 is an exemplary view of an organic electric device according to an embodiment of the present invention.

Referring to FIG. 1, an organic electric device 100 according to an embodiment of the present invention may include a first electrode 120, a second electrode 180, and a first electrode 120 formed on a substrate 110. An organic material layer including the compound according to the present invention is included between the second electrodes 180. In this case, the first electrode 120 may be an anode (anode), the second electrode 180 may be a cathode (cathode), and in the case of an inverted type, the first electrode may be a cathode and the second electrode may be an anode.

The organic layer may include a hole injection layer 130, a hole transport layer 140, a light emitting layer 150, an electron transport layer 160, an electron injection layer 170, etc. sequentially stacked on the first electrode 120. . In this case, at least one of these layers may be omitted, or may further include a hole blocking layer, an electron blocking layer, a light emitting auxiliary layer 151, an electron transport auxiliary layer, a buffer layer 141, and the like. It may also serve as a hole blocking layer.

In addition, although not shown, the organic electronic device according to an embodiment of the present invention may further include a protective layer or a light efficiency improving layer. The light efficiency improving layer may be formed on a surface not in contact with the organic material layer on both surfaces of the first electrode or on a surface not in contact with the organic material layer on both surfaces of the second electrode.

On the other hand, when using a single compound as a host material of the light emitting layer, and when using a mixture of heterogeneous compounds, the band gap, electrical characteristics, interfacial characteristics, etc. may vary. In order to improve the electrical properties such as lifetime, efficiency, etc., it is very important to determine which compound each component of the mixture is composed of.

In the present invention, by using a mixture of the various compounds represented by the formula (1), (2) and (3) as the host material of the light emitting layer, the energy level and T ₁ value between each organic layer, the intrinsic properties (mobility, interface characteristics, etc.) between the organic layer ) To improve the lifespan and efficiency of organic electric devices.

The organic electroluminescent device 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, the anode 120 is formed by depositing a metal or conductive metal oxide or an alloy thereof on a substrate, and the hole injection layer 130 thereon. , By forming an organic material layer including the hole transport layer 140, the light emitting layer 150, the electron transport layer 160 and the electron injection layer 170, and then depositing a material that can be used as the cathode 180 thereon have. In addition, the light emitting auxiliary layer 151 may be further formed between the hole transport layer 140 and the light emitting layer 150, and an electron transport auxiliary layer may be further formed between the light emitting layer 150 and the electron transport layer 160.

In addition, the organic layer may be formed by using various polymer materials, but not by a deposition process or a solvent process 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, and a doctor blade. It can be produced in fewer layers by methods such as ding process, screen printing process, or thermal transfer method. Since the organic material layer according to the present invention can be formed in various ways, the scope of the present invention is not limited by the forming method.

The organic electric element according to an embodiment of the present invention may be a top emission type, a bottom emission type, or a double-sided emission type according to a material used.

In addition, the organic electroluminescent device according to an embodiment of the present invention may be selected from the group consisting of an organic electroluminescent device, an organic solar cell, an organic photosensitive member, an organic transistor, a monochromatic lighting device and a quantum dot display device.

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 a mobile communication terminal such as a mobile phone, a PDA, an electronic dictionary, a PMP, a remote controller, a navigation device, a game machine, various TVs, and various computers.

Hereinafter, an organic electric device according to an aspect of the present invention will be described.

An organic electric device according to an aspect of the present invention includes a first electrode, a second electrode, and an organic material layer formed between the first electrode and the second electrode. In this case, the organic material layer includes a phosphorescent light emitting layer, and the host of the phosphorescent light emitting layer includes a first compound represented by Chemical Formula 1, a second compound represented by Chemical Formula 2, and a third compound represented by Chemical Formula 3 do.

    <Formula 1> <Formula 2>

<Formula 3>

Hereinafter, the symbols used in the respective chemical formulas will be described.

First, each symbol of General formula (1) is demonstrated.

Ring A and Ring B are each independently an aromatic ring of C ₆ -C ₂₀ or a hetero ring of C ₂ -C ₂₀ . However, when one of the A ring and the B ring is a single ring, the other one is a polycyclic ring in which two or more rings are condensed or adjacent R ¹ are bonded to each other to form a ring. Thus, the compound of formula 1 is a polycyclic compound in which at least six rings are fused. For example, when ring A is benzene ring, ring B is a polycyclic ring compound such as naphthalene, phenanthrene or the like, or adjacent R ^{1 is} bonded to each other to form a ring such as benzene or naphthalene, resulting in a total of 6 or more polycyclic rings.

When the ring A and ring B is an aromatic ring, preferably an aromatic ring of C ₆ ~ C ₁₄ , for example, may be benzene, naphthalene, phenanthrene and the like.

The A ring may be substituted with one or more R ² , the B ring with one or more R ³ , and R ² and R ³ may be each independently hydrogen; heavy hydrogen; halogen; Cyano group; C ₆ ~ C ₆₀ aryl group; Fluorenyl groups; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; Aliphatic ring group of C ₃ ~ C ₆₀ ; A fused ring group of an aliphatic ring of C ₃ ~ C ₆₀ and an aromatic ring of C ₆ ~ C ₆₀ ; C ₁ ~ C ₅₀ Alkyl group; C ₂ ~ C ₂₀ Alkenyl group; Alkynyl groups of C ₂ to C ₂₀ ; C ₁ ~ C ₃₀ Alkoxy group; C ₆ -C ₃₀ aryloxy group; And -L'-N (R _a ) (R _b ); and a plurality of R ² and R ³ may be the same as or different from each other.

When R ² and R ³ are aryl groups, they may preferably be C ₆ to C ₃₀ aryl groups, more preferably C ₆ to C ₁₈ aryl groups such as phenyl, naphthyl, biphenyl, terphenyl and the like. .

When R ² and R ³ are alkenyl groups, they may preferably be C ₂ to C ₂₀ alkenyl groups, more preferably C ₂ to C ₂₀ alkenyl groups such as ethene, propene and the like.

X ¹ and X ² are each independently a single bond, N- (L-Ar), O, S or C (R ') (R "), l and m are each an integer of 0 or 1, and l + m Is an integer greater than or equal to 1. If l or m is 0, X ¹ or X ² is absent, which means that the adjacent carbon atoms are bonded directly to each other rather than to X ¹ or X ² . Since m is an integer of 1 or more, it is excluded when X ¹ and X ² are single bonds at the same time.

When both X ¹ and X ² are N- (L-Ar) or C (R ') (R "), each of a plurality of L, each of a plurality of Ar, each of a plurality of R', each of a plurality of R" It can be the same or different.

Ar ¹ and Ar are C ₆ ~ C ₆₀ An aryl group; Fluorenyl groups; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; Aliphatic ring group of C ₃ ~ C ₆₀ ; A fused ring group of an aliphatic ring of C ₃ ~ C ₆₀ and an aromatic ring of C ₆ ~ C ₆₀ ; And -L'-N (R _a ) (R _b ); may be selected from the group consisting of.

When Ar ¹ and Ar are an aryl group, preferably an aryl group of C ₆ to C ₃₀ , more preferably an aryl group of C ₆ to C ₁₈ , such as phenyl, naphthyl, biphenyl, terphenyl, phenanthrene, Triphenylene and the like.

When Ar ¹ and Ar are heterocyclic groups, preferably a heterocyclic group of C ₂ to C ₃₀ , more preferably a heterocyclic group of C ₂ to C ₁₆ , such as pyridine, pyrimidine, triazine, quinoline, quina Sleepy, quinoxaline, benzothienopyrimidine, benzofuropyrimidine, naphthopurypyrimidine, benzoquinazoline, dibenzothiophene, benzimidazole, dibenzoquinazoline and the like.

When Ar ¹ and Ar are fluorenyl groups, they may be 9,9-dimethylfluorene, 9,9-diphenylfluorene, and the like.

L ¹ and L are a single bond; C ₆ ~ C ₆₀ arylene group; Fluorenylene groups; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; Aliphatic ring group of C ₃ ~ C ₆₀ ; And a fused ring group of C ₃ to C ₆₀ aliphatic rings and C ₆ to C ₆₀ aromatic rings.

When L ¹ and L are arylene groups, it may be preferably an arylene group of C ₆ ~ C ₃₀ , more preferably an arylene group of C ₆ ~ C ₁₈ , such as phenyl, naphthyl, biphenyl, terphenyl and the like. .

When L ¹ and L are heterocyclic groups, preferably a heterocyclic group of C ₂ to C ₃₀ , more preferably a heterocyclic group of C ₂ to C ₁₆ , such as pyridine, pyrimidine, triazine, quinoline, quina Sleepy, quinoxaline, benzimidazole, benzothienopyrimidine, naphthopuropyrimidine, benzoquinazolin, dibenzoquinazolin, dibenzothiophene, benzofurypyrimidine and the like.

R 'and R "are hydrogen; deuterium; halogen; C ₆ ~ C ₆₀ aryl group; fluorenyl group; C ₂ ~ C ₆₀ of at least one heteroatom including O, N, S, Si and P Heterocyclic group; C ₃ ~ C ₆₀ aliphatic ring; C ₃ ~ C ₆₀ aliphatic ring and C ₆ ~ C ₆₀ aromatic ring; C ₁ ~ C ₅₀ Alkyl group; C ₂ ~ C ₂₀ Alkenyl group; C ₂ ~ C ₂₀ Alkynyl group; C ₁ ~ C ₃₀ Alkoxy group; C ₆ ~ C ₃₀ An aryloxy group; and -L'-N (R _a ) (R _b ); And R 'and R "may combine with each other to form a ring. When R 'and R "are bonded to each other to form a ring, a spiro compound may be formed together with C to which they are bonded.

When R 'and R "are an aryl group, it may be a C ₆ -C ₃₀ aryl group, more preferably a C ₆ -C ₁₂ aryl group, for example, phenyl, biphenyl, naphthyl and the like.

When R 'and R "are alkyl groups, it may be preferably an alkyl group of C ₁ to C ₁₀ , more preferably an alkyl group of C ₁ to C ₄ , such as methyl, t-butyl and the like.

R ¹ is hydrogen; heavy hydrogen; halogen; Cyano group; C ₆ ~ C ₆₀ aryl group; Fluorenyl groups; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; Aliphatic ring group of C ₃ ~ C ₆₀ ; A fused ring group of an aliphatic ring of C ₃ ~ C ₆₀ and an aromatic ring of C ₆ ~ C ₆₀ ; C ₁ ~ C ₅₀ Alkyl group; C ₂ ~ C ₂₀ Alkenyl group; Alkynyl groups of C ₂ to C ₂₀ ; C ₁ ~ C ₃₀ Alkoxy group; C ₆ -C ₃₀ aryloxy group; And -L'-N (R _a ) (R _b ); It is selected from the group consisting of, neighboring groups may combine with each other to form a ring.

Adjacent R ¹ is a ring formed by bonding to each other C ₆ ~ C ₆₀ An aromatic ring group; Fluorenyl groups; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; Aliphatic ring group of C ₃ ~ C ₆₀ ; Or it may be a fused ring group of an aromatic ring of C ₃ ~ C ₆₀ of aliphatic rings and C ₆ ~ C _60. For example, when adjacent R ^{1 is} bonded to each other, an aromatic ring such as benzene, naphthalene, phenanthrene, or the like may be formed.

a is an integer of 0 to 2, and when a is an integer of 2 or more, each of R ¹ may be the same as or different from each other.

When R ¹ is a heterocyclic group, preferably a heterocyclic group of C ₂ to C ₃₀ , more preferably a heterocyclic group of C ₂ to C ₂₂ , such as carbazole, phenyl-carbazole, naphthyl-carbazole And the like.

L ′ is a single bond independently of each other; C ₆ ~ C ₆₀ arylene group; Fluorenylene groups; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; Aliphatic ring group of C ₃ ~ C ₆₀ ; And a fused ring group of C ₃ to C ₆₀ aliphatic rings and C ₆ to C ₆₀ aromatic rings.

R _a and R _b are each independently a C ₆ ~ C ₆₀ aryl group; Fluorenyl groups; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; Aliphatic ring group of C ₃ ~ C ₆₀ ; And a fused ring group of C ₃ to C ₆₀ aliphatic rings and C ₆ to C ₆₀ aromatic rings.

R ¹ , R ² , R ³ , Ar ¹ , Ar, L ¹ , L ', L, R _a , R _b , R', R ", and the ring formed by combining adjacent groups are each deuterium; halogen; Silane substituted or unsubstituted with a C ₁ -C ₂₀ alkyl group or a C ₆ -C ₂₀ aryl group; siloxane group; boron group; germanium group; cyano group; nitro group; C ₁ -C ₂₀ alkylthio group; C ₁ -C ₂₀ alkoxy group; C ₆ -C ₂₀ aryloxy group; an alkyl group of C ₁ -C _20; alkynyl of _{C 2 -C 20;; C 2} -C 20 alkenyl group of C ₆ -C ₂₀ Aryl group; C ₆ -C ₂₀ aryl group substituted with deuterium; fluorenyl group; C ₂ -C ₂₀ heterocycle including at least one heteroatom selected from the group consisting of O, N, S, Si and P An aliphatic ring group of C ₃ -C ₂₀ , an arylalkyl group of C ₇ -C _20, an arylalkenyl group of C ₈ -C ₂₀ , -L'-N (R _a ) (R _b ); and combinations thereof It may be further substituted with one or more substituents selected from the group consisting of.

Each symbol in Formula 2 may be defined as follows.

X ⁴ to X ⁸ are independently of each other C (R ^c ) or N. Thus, the ring comprising X ⁴ to X ⁸ may be an aromatic ring or a hetero ring containing N.

For example, when the ring containing X ⁴ to X ⁸ is an aromatic ring, it may be preferably an aromatic ring of C ₆ ~ C ₃₀ , more preferably an aromatic ring of C ₆ ~ C ₁₈ , containing N In the case of a heterocyclic group, C ₂ ~ C _{30 It} is preferably a heterocyclic group, more preferably C ₂ ~ C _{18 It} may be a heterocyclic group. For example, a ring comprising X ⁴ to X ⁸ may be selected from phenyl, naphthalene, triphenylene, phenanthrene, triazine, pyrimidine, pyridine, quinoline, quinazoline, quinoxaline, carbazole, phenylcarbazole, benzoquinoxaline, Benzoquinazoline, benzopuroquinazoline and the like.

R ³⁰ and R ³¹ are each independently hydrogen; heavy hydrogen; halogen; C ₆ ~ C ₆₀ aryl group; Fluorenyl groups; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; Aliphatic ring group of C ₃ ~ C ₆₀ ; C ₁ ~ C ₅₀ Alkyl group; C ₂ ~ C ₂₀ Alkenyl group; Alkynyl groups of C ₂ to C ₂₀ ; C ₁ ~ C ₃₀ Alkoxy group; C ₆ -C ₃₀ aryloxy group; And -L'-N (R _a ) (R _b ); It is selected from the group consisting of, neighboring groups may combine with each other to form a ring.

R ^c is hydrogen; heavy hydrogen; halogen; Cyano group; Nitro group; C ₆ -C ₂₀ aryl group; Fluorenyl groups; C ₂ ~ C ₂₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; Aliphatic ring group of C ₃ ~ C ₂₀ ; A fused ring group of an aliphatic ring of C ₃ ~ C ₂₀ and an aromatic ring of C ₆ ~ C ₂₀ ; C ₁ ~ C ₂₀ Alkyl group; C ₂ ~ C ₂₀ Alkenyl group; Alkynyl groups of C ₂ to C ₂₀ ; C ₁ ~ C ₂₀ Alkoxy group; C ₆ -C ₃₀ aryloxy group; And -L ^a -N (R ^a ) (R ^b ); and adjacent groups can be bonded to each other to form a ring.

Ring group between the adjacent R ^30, form a bond to one another between the adjacent R ^31, or adjacent to each other a ring R ^c is C ₆ ~ C _60; Fluorenyl groups; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; Aliphatic ring group of C ₃ ~ C ₆₀ ; Or it may be a fused ring group of an aromatic ring of C ₃ ~ C ₆₀ of aliphatic rings and C ₆ ~ C _60.

When adjacent R ³⁰ or adjacent R ³¹ combine with each other to form an aromatic ring, C ₆ ~ C ₃₀ aromatic ring group, more preferably C ₆ ~ C ₁₂ aromatic ring group, for example, Rings such as benzene and naphthalene may be formed, and in the case of forming heterocycles, C ₂ to C ₃₀ heterocyclic groups, more preferably C ₂ to C ₁₀ heterocyclic groups such as thiophene , Benzothiophene, furan, benzofuran, pyrrole, phenylpyrrole, indole, phenylindole, and the like, when forming an aliphatic ring, C ₃ ~ C ₃₀ aliphatic ring, more preferably C Aliphatic rings of ₃ to C ₁₁ , such as 5,5-dimethylcyclopenta-1,3-diene, dimethylindene and the like can be formed.

In addition, when adjacent R ^c are bonded to each other to form an aromatic ring, C ₆ ~ C ₃₀ aromatic ring group, more preferably C ₆ ~ C ₁₄ aromatic ring group, for example, benzene, naphthalene, When a ring such as phenanthrene can be formed, and a heterocyclic ring is formed, a heterocyclic group of C ₂ to C ₃₀ is preferred, more preferably a heterocyclic group of C ₂ to C ₁₀ such as thiophene, Benzothiophene, furan, benzofuran, pyrrole, phenylpyrrole, indole, phenylindole and the like can be formed.

p is an integer of 0-4, q is an integer of 0-4, and when each of these is an integer of 2 or more, each R <^30> , each R <^31> may be mutually same or different.

When R ³⁰ and R ³¹ are aryl groups, they may preferably be C ₆ to C ₃₀ aryl groups, more preferably C ₆ to C ₁₈ aryl groups such as phenyl, naphthyl, biphenyl, terphenyl and the like. .

When R ³⁰ and R ³¹ are heterocyclic groups, preferably C ₂ to C ₃₀ heterocyclic groups, more preferably C ₂ to C ₂₈ heterocyclic groups such as carbazole, phenylcarbazole, naphthylcarba Sol, terphenylcarbazole, benzocarbazole, benzocarbazole substituted with biphenyl, dibenzothiophene, benzonaphthothiophene, dibenzofuran, benzonaphthofuran, benzothienocarbazole, benzofuro Carbazole and the like.

When R ³⁰ and R ³¹ are alkyl groups, they may preferably be C ₁ to C ₁₀ alkyl groups, more preferably C ₁ to C ₄ alkyl groups such as methyl, t-butyl and the like, and R ³⁰ and R ³¹ may be In the case of a fluorenyl group, it may be 9,9-dimethylfluorene, 9,9-diphenylfluorene, 9,9'-spirofluorene, or the like.

L ′, R _a and R _b are the same as defined in Chemical Formula 1.

The R ³⁰ , R ³¹ , R ^c , L ', R _a , R _b , and a ring formed by combining adjacent groups with each other include deuterium; halogen; A silane group unsubstituted or substituted with a C ₁ -C ₂₀ alkyl group or a C ₆ -C ₂₀ aryl group; Siloxane groups; Boron group; Germanium group; Cyano group; Nitro group; Import alkylthio of C ₁ -C _20; An alkoxy group of C ₁ -C ₂₀ ; C ₆ -C ₂₀ arylalkoxy group; An alkyl group of C ₁ -C ₂₀ ; Alkenyl groups of C ₂ -C ₂₀ ; An alkynyl group of C ₂ -C ₂₀ ; C ₆ -C ₂₀ aryl group; C ₆ -C ₂₀ aryl group substituted with deuterium; Fluorenyl groups; C ₂ -C ₂₀ heterocyclic group including at least one heteroatom selected from the group consisting of O, N, S, Si and P; Aliphatic ring groups of C ₃ -C ₂₀ ; C ₇ -C ₂₀ arylalkyl group; Arylalkenyl group of C ₈ -C ₂₀ ; -L'-N (R _a ) (R _b ); And one or more substituents selected from the group consisting of a combination thereof.

Each symbol in Formula 3 may be defined as follows.

X ₄ to X ₆ are each independently C- (L-Ar ′) or N, and at least one of X ₄ to X ₆ is N. Thus, the ring comprising X ₄ to X ₆ may be a pyridine derivative, pyrimidine derivative or triazine derivative.

Ar ⁶ to Ar ⁸ independently of each other C ₆ ~ C ₆₀ An aryl group; Fluorenyl groups; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; Aliphatic ring group of C ₃ ~ C ₆₀ ; A fused ring group of an aliphatic ring of C ₃ ~ C ₆₀ and an aromatic ring of C ₆ ~ C ₆₀ ; And combinations thereof may be selected from the group.

When Ar ⁶ to Ar ⁸ is an aryl group, preferably an aryl group of C ₆ to C ₃₀ , more preferably an aryl group of C ₆ to C ₁₈ , such as phenyl, biphenyl, naphthyl, terphenyl, anthracene, Pyrene, phenanthrene, triphenylene and the like.

When Ar ⁶ to Ar ⁸ are heterocyclic groups, preferably C ₂ to C ₃₀ heterocyclic groups, more preferably C ₂ to C ₂₁ heterocyclic groups such as pyridine, dibenzothiophene, dibenzofuran , Quinazoline, quinoxaline, quinoline, phenanthroline, imidazole, benzonaphthyridine, benzoquinoline, benzothienopyrimidine, benzofurypyrimidine, benzoacridine, dibenzoacridine and the like.

When Ar ⁶ to Ar ⁸ is a fluorenyl group, it may be 9,9-dimethylfluorene, 9,9-diphenylfluorene, 9,9'-spirofluorene, or the like.

L ⁴ to L ⁶ are each independently a single bond; C ₆ ~ C ₆₀ arylene group; Fluorenylene groups; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; Aliphatic ring group of C ₃ ~ C ₆₀ ; A fused ring group of an aliphatic ring of C ₃ ~ C ₆₀ and an aromatic ring of C ₆ ~ C ₆₀ ; And combinations thereof may be selected from the group.

When L ⁴ to L ⁶ are an arylene group, preferably an arylene group of C ₆ to C ₃₀ , more preferably an arylene group of C ₆ to C ₁₈ , for example, phenyl, biphenyl, naphthyl, terphenyl, etc. have.

When L ⁴ to L ⁶ are heterocyclic groups, preferably C ₂ to C ₃₀ heterocyclic groups, more preferably C ₂ to C ₁₂ heterocyclic groups such as pyridine, quinazoline, benzoquinazolin, quinox Saline, dibenzothiophene, dibenzofuran and the like.

Ar 'is hydrogen; heavy hydrogen; halogen; A silane group unsubstituted or substituted with a C ₁ -C ₂₀ alkyl group or a C ₆ -C ₂₀ aryl group; Cyano group; Nitro group; Import alkylthio of C ₁ -C _20; An alkoxy group of C ₁ -C ₂₀ ; C ₆ -C ₂₀ aryloxy group; An alkyl group of C ₁ -C ₂₀ ; Alkenyl groups of C ₂ -C ₂₀ ; An alkynyl group of C ₂ -C ₂₀ ; C ₆ ~ C ₆₀ aryl group; Fluorenyl groups; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; Aliphatic ring group of C ₃ ~ C ₆₀ ; A fused ring group of an aliphatic ring of C ₃ ~ C ₆₀ and an aromatic ring of C ₆ ~ C ₆₀ ; And -L'-N (R _a ) (R _b ); may be selected from the group consisting of.

L is independently of each other a single bond; C ₆ ~ C ₆₀ arylene group; Fluorenylene groups; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; Aliphatic ring group of C ₃ ~ C ₆₀ ; And a fused ring group of C ₃ to C ₆₀ aliphatic rings and C ₆ to C ₆₀ aromatic rings.

Ar ⁶ to Ar ⁸ , Ar, Ar ', L ⁴ to L ⁶ , L, L', R _a , R _b , R ^a , and R ^b are each deuterium; halogen; A silane group unsubstituted or substituted with a C ₁ -C ₂₀ alkyl group or a C ₆ -C ₂₀ aryl group; Siloxane groups; Boron group; Germanium group; Cyano group; Nitro group; Import alkylthio of C ₁ -C _20; An alkoxy group of C ₁ -C ₂₀ ; C ₆ -C ₂₀ aryloxy group; An alkyl group of C ₁ -C ₂₀ ; Alkenyl groups of C ₂ -C ₂₀ ; An alkynyl group of C ₂ -C ₂₀ ; C ₆ -C ₂₀ aryl group; C ₆ -C ₂₀ aryl group substituted with deuterium; Fluorenyl groups; C ₂ -C ₂₀ heterocyclic group including at least one heteroatom selected from the group consisting of O, N, S, Si and P; Aliphatic ring groups of C ₃ -C ₂₀ ; C ₇ -C ₂₀ arylalkyl group; Arylalkenyl group of C ₈ -C ₂₀ ; -L'-N (R _a ) (R _b ); And one or more substituents selected from the group consisting of a combination thereof.

Preferably, in Formula 1, Ring A and Ring B may be independently selected from the group consisting of the following Formula a-1 to Formula a-7.

<Formula a-1> <Formula a-2> <Formula a-3> <Formula a-4>

<Formula a-5>    <Formula a-6>        <Formula a-7>

In the above chemical formula, each symbol may be defined as follows, and * denotes a binding site.

Z ¹ to Z ⁴⁸ are independently of each other C, C (R ^c ) or N. When Z ¹ to Z ⁴⁸ is C, the substituent R ¹ or R ² may be bonded to C, or may be bonded to L ² or L ³ .

R ^c is the same as defined in Chemical Formula 2. That is, R ^c is hydrogen; heavy hydrogen; halogen; Cyano group; Nitro group; C ₆ -C ₂₀ aryl group; Fluorenyl groups; C ₂ ~ C ₂₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; Aliphatic ring group of C ₃ ~ C ₂₀ ; A fused ring group of an aliphatic ring of C ₃ ~ C ₂₀ and an aromatic ring of C ₆ ~ C ₂₀ ; C ₁ ~ C ₂₀ Alkyl group; C ₂ ~ C ₂₀ Alkenyl group; Alkynyl groups of C ₂ to C ₂₀ ; C ₁ ~ C ₂₀ Alkoxy group; C ₆ -C ₂₀ aryloxy group; And -L ^a -N (R ^a ) (R ^b ); and adjacent R ^c may combine with each other to form a ring.

L ^a , R ^a and R ^b are the same as defined in Formula 2.

Preferably, in Formula 1 to Formula 3, L ¹ to L ⁴ may be independently selected from the group consisting of the following Formulas b-1 to b-13.

<Formula b-1> <Formula b-2> <Formula b-3> <Formula b-4> <Formula b-5> <Formula b-6>

<Formula b-7> <Formula b-8> <Formula b-9> <Formula b-10>

<Formula b-11> <Formula b-12> <Formula b-13>

In the above formula, each symbol may be defined as follows.

R ⁴ to R ⁶ are each independently hydrogen; heavy hydrogen; halogen; Cyano group; Nitro group; C ₆ -C ₂₀ aryl group; Fluorenyl groups; C ₂ ~ C ₂₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; Aliphatic ring group of C ₃ ~ C ₂₀ ; A fused ring group of an aliphatic ring of C ₃ ~ C ₂₀ and an aromatic ring of C ₆ ~ C ₂₀ ; C ₁ ~ C ₂₀ Alkyl group; C ₂ ~ C ₂₀ Alkenyl group; Alkynyl groups of C ₂ to C ₂₀ ; C ₁ ~ C ₂₀ Alkoxy group; C ₆ -C ₂₀ aryloxy group; And -L ^a -N (R ^a ) (R ^b ); and adjacent groups can be bonded to each other to form a ring.

Y is independently of each other N- (L ^a -Ar ^a ), O, S or C (R ^d ) (R ^e ), Z ⁴⁹ to Z ⁵¹ are independently of each other C, C (R ^c ) or N, At least one of Z ⁴⁹ to Z ⁵¹ is N.

f, h, i and j are each an integer of 0 to 4, g is an integer of 0 to 6, k and l 'are each an integer of 0 to 3, m' is an integer of 0 to 2, n is An integer from 0 to 3, each of which is an integer of 2 or more, wherein each R ⁴ , each R ⁵ , and each R ⁶ is the same or different from each other,

R ^c , R ^d and R ^e are each independently hydrogen; heavy hydrogen; halogen; Cyano group; Nitro group; C ₆ -C ₂₀ aryl group; Fluorenyl groups; C ₂ ~ C ₂₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; Aliphatic ring group of C ₃ ~ C ₂₀ ; A fused ring group of an aliphatic ring of C ₃ ~ C ₂₀ and an aromatic ring of C ₆ ~ C ₂₀ ; C ₁ ~ C ₂₀ Alkyl group; C ₂ ~ C ₂₀ Alkenyl group; Alkynyl groups of C ₂ to C ₂₀ ; C ₁ ~ C ₂₀ Alkoxy group; C ₆ -C ₂₀ aryloxy group; And -L ^a -N (R ^a ) (R ^b ); and R ^d and R ^e may be bonded to each other or adjacent R ^c may be bonded to each other to form a ring. When R ^d and R ^e are bonded to each other to form a ring, a spiro compound is formed.

Ar ^a is a C ₆ ~ C ₂₀ aryl group; Fluorenyl groups; C ₂ ~ C ₂₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; Aliphatic ring group of C ₃ ~ C ₂₀ ; And combinations thereof may be selected from the group.

L ^a , R ^a and R ^b are the same as defined in Formula 2.

Preferably, Formula 1 may be represented by the following Formula 1-A or 1-B.

   <Formula 1-A> <Formula 1-B>

In the above formula, A ring, B ring, R ¹ , L ¹ , Ar ¹ , X ¹ , X ² and a are the same as defined in formula (1).

Preferably, Formula 1 may be represented by one of Formula 1-1 to Formula 1-44.

<Formula 1-1> <Formula 1-2> <Formula 1-3>

<Formula 1-4> <Formula 1-5> <Formula 1-6> <Formula 1-7>

<Formula 1-8> <Formula 1-9> <Formula 1-10> <Formula 1-11>

<Formula 1-12> <Formula 1-13> <Formula 1-14> <Formula 1-15>

<Formula 1-16> <Formula 1-17> <Formula 1-18> <Formula 1-19>

<Formula 1-20> <Formula 1-21> <Formula 1-22> <Formula 1-23>

<Formula 1-24> <Formula 1-25> <Formula 1-26>

<Formula 1-27> <Formula 1-28> <Formula 1-29> <Formula 1-30>

<Formula 1-31> <Formula 1-32> <Formula 1-33> <Formula 1-34>

<Formula 1-35> <Formula 1-36> <Formula 1-37> <Formula 1-38>

<Formula 1-39> <Formula 1-40> <Formula 1-41> <Formula 1-42>

Each symbol in the formula may be defined as follows.

R ¹¹ is independently of each other hydrogen; heavy hydrogen; halogen; C ₆ -C ₂₀ aryl group; Fluorenyl groups; C ₂ ~ C ₂₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; Aliphatic ring group of C ₃ ~ C ₂₀ ; A fused ring group of an aliphatic ring of C ₃ ~ C ₂₀ and an aromatic ring of C ₆ ~ C ₂₀ ; C ₁ ~ C ₂₀ Alkyl group; C ₂ ~ C ₂₀ Alkenyl group; Alkynyl groups of C ₂ to C ₂₀ ; C ₁ ~ C ₂₀ Alkoxy group; C ₆ -C ₂₀ aryloxy group; And -L ^a -N (R ^a ) (R ^b ); and adjacent groups can be bonded to each other to form a ring.

b, c and a 'are each an integer from 0 to 4, b' and c 'are each an integer from 0 to 6, b "and c" are each an integer from 0 to 8, and each of them is an integer of 2 or more. , Each R ¹ , each R ² , each R ³ , each R ¹¹ are the same or different from each other.

X ¹ , X ² , Ar ¹ , L ¹ , R ¹ , R ² , R ³ and a are as defined in Formula 1, and L ^a , R ^a and R ^b are as defined in Formula 2.

Preferably, Formula 1 may be represented by one of the following Formula 1-C to Formula 1-J.

<Formula 1-C> <Formula 1-D> <Formula 1-E> <Formula 1-F>

<Formula 1-G> <Formula 1-H> <Formula 1-I> <Formula 1-J>

In the above formula, A ring, B ring, R ¹ , R ', R ", L ¹ , L, Ar ¹ , Ar and a are the same as defined in the formula (1).

Preferably, Formula 2 may be represented by the following Formula 2-A or 2-B.

<Formula 2-A>        <Formula 2-B>

In the above formula, each symbol may be defined as follows.

L ₄ is a single bond; C ₆ ~ C ₆₀ arylene group; Fluorenylene groups; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; Aliphatic ring group of C ₃ ~ C ₆₀ ; And a fused ring group of C ₃ to C ₆₀ aliphatic rings and C ₆ to C ₆₀ aromatic rings.

When L ₄ is an arylene group, it may be preferably an arylene group of C ₆ to C ₃₀ , more preferably an arylene group of C ₆ to C ₁₈ , such as phenyl, biphenyl, naphthalene, terphenyl and the like.

When L ₄ is a heterocyclic group, it may be preferably a C ₂ ~ C ₃₀ heterocyclic group, more preferably a C ₂ ~ C ₁₂ heterocyclic group, such as dibenzofuran, dibenzothiophene and the like.

R ³² to R ³⁴ are each independently hydrogen; heavy hydrogen; halogen; Cyano group; Nitro group; C ₆ -C ₂₀ aryl group; Fluorenyl groups; C ₂ ~ C ₂₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; Aliphatic ring group of C ₃ ~ C ₂₀ ; A fused ring group of an aliphatic ring of C ₃ ~ C ₂₀ and an aromatic ring of C ₆ ~ C ₂₀ ; C ₁ ~ C ₂₀ Alkyl group; C ₂ ~ C ₂₀ Alkenyl group; Alkynyl groups of C ₂ to C ₂₀ ; C ₁ ~ C ₂₀ Alkoxy group; C ₆ -C ₂₀ aryloxy group; And -L ^a -N (R ^a ) (R ^b ); It can be selected from the group consisting of, neighboring groups can combine with each other to form a ring.

When each of R ³² to R ³⁴ is an aryl group, preferably, a C ₆ to C ₁₈ aryl group such as phenyl, naphthyl, biphenyl, terphenyl and the like.

r is an integer from 0 to 3, s is an integer from 0 to 5, t is an integer from 0 to 4, u is an integer from 0 to 4, each of R ³² , each of which is an integer of 2 or more, each R ³³ , each R ³⁴ may be the same as or different from each other.

X ⁹ is N- (L ^a -Ar ^a ), O, S, C (R ^c ), C (R ^d ) (R ^e ) or N.

R ^c , R ^d and R ^e are each independently hydrogen; heavy hydrogen; halogen; Cyano group; Nitro group; C ₆ -C ₂₀ aryl group; Fluorenyl groups; C ₂ ~ C ₂₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; Aliphatic ring group of C ₃ ~ C ₂₀ ; A fused ring group of an aliphatic ring of C ₃ ~ C ₂₀ and an aromatic ring of C ₆ ~ C ₂₀ ; C ₁ ~ C ₂₀ Alkyl group; C ₂ ~ C ₂₀ Alkenyl group; Alkynyl groups of C ₂ to C ₂₀ ; C ₁ ~ C ₂₀ Alkoxy group; C ₆ -C ₂₀ aryloxy group; And -L ^a -N (R ^a ) (R ^b ); may be selected from the group consisting of. R ^d and R ^e may be bonded to each other to form a ring, in which case a spiro compound is formed. In addition, adjacent R ^c may be bonded to each other to form a ring.

Ar ^a is a C ₆ ~ C ₂₀ aryl group; Fluorenyl groups; C ₂ ~ C ₂₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; Aliphatic ring group of C ₃ ~ C ₂₀ ; And combinations thereof may be selected from the group.

R ³⁰ , R ³¹ , X ⁴ to X ⁸ , L ^a , R ^a , R ^b , p are as defined in formula (2).

Preferably, Formula 2 may be represented by one of the following Formula 2-C to Formula 2-F.

<Formula 2-C> <Formula 2-D> <Formula 2-E> <Formula 2-F>

Wherein p 'is an integer from 0 to 6, p "is an integer from 0 to 8, and each of them is an integer of 2 or more, each R ³⁰ , each R ³¹ is the same as or different from each other, X ⁴ To X ⁸ , R ³⁰ , R ³¹ and q are as defined in formula (2).

Also, preferably, Chemical Formula 2 may be represented by the following Chemical Formula 2-G.

<Formula 2-G>

In the above formula, v and w are each an integer of 0 to 2, v + w is an integer of 1 or more, and X ⁴ to X ⁸ are as defined in formula (2).

Preferably, Chemical Formula 3 may be represented by one of the following Chemical Formulas 3-A to 3-C.

   <Formula 3-A> <Formula 3-B> <Formula 3-C>

In the above formula, L ⁴ to L ⁶ , Ar ⁶ to Ar ⁸ are the same as defined in the formula (3).

In addition, Chemical Formula 3 may be represented by one of the following Chemical Formulas 3-1 to 3-8.

<Formula 3-1> <Formula 3-2>

<Formula 3-3> <Formula 3-4>

<Formula 3-5> <Formula 3-6>

<Formula 3-7> <Formula 3-8>

In the above formula, each symbol may be defined as follows.

X ₄ to X ₆ , L ⁴ to L ⁶ , Ar ⁷ , Ar ⁸ are the same as defined in Chemical Formula 3.

X ₇ and X ₈ are independently of each other a single bond, N- (L ^a -Ar ^a ), O, S or C (R ^d ) (R ^e ), at least one of which is not a single bond.

Y ¹ to Y ³⁸ are independently of each other C, C (R _c ) or N. It is C connected with the linking group L ⁴ among Y ¹ to Y ³⁸ . For example, when associated with a 3-1 in formula, Y ¹ to Y ⁴ in Y ¹ is L ^4, Y ¹ is a C, and the other Y ² to Y ⁴ are independently C (R _c) or N with each other.

R _c , R ^d and R ^e are each independently hydrogen; heavy hydrogen; halogen; Cyano group; An alkyl group of C ₁ -C ₂₀ ; Alkenyl groups of C ₂ -C ₂₀ ; An alkynyl group of C ₂ -C ₂₀ ; C ₆ -C ₂₀ aryl group; Fluorenyl groups; C ₂ -C ₂₀ heterocyclic group including at least one heteroatom selected from the group consisting of O, N, S, Si and P; Aliphatic ring groups of C ₃ -C ₂₀ ; -L ^a -N (R ^a ) (R ^b ); And it may be selected from the group consisting of a combination thereof, adjacent R _c or R ^d and R ^e may be bonded to each other to form a ring. At this time, the ring is C ₆ ~ C ₆₀ Aromatic ring group; Fluorenyl groups; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; Aliphatic ring group of C ₃ ~ C ₆₀ ; Or it may be a fused ring group of an aromatic ring of C ₃ ~ C ₆₀ of aliphatic rings and C ₆ ~ C _60.

R ¹³ is independently of each other hydrogen; heavy hydrogen; halogen; A silane group unsubstituted or substituted with a C ₁ -C ₂₀ alkyl group or a C ₆ -C ₂₀ aryl group; Siloxane groups; Boron group; Germanium group; Cyano group; Nitro group; Import alkylthio of C ₁ -C _20; An alkoxy group of C ₁ -C ₂₀ ; C ₆ -C ₂₀ aryloxy group; An alkyl group of C ₁ -C ₂₀ ; Alkenyl groups of C ₂ -C ₂₀ ; An alkynyl group of C ₂ -C ₂₀ ; C ₆ -C ₂₀ aryl group; C ₆ -C ₂₀ aryl group substituted with deuterium; Fluorenyl groups; C ₂ -C ₂₀ heterocyclic group including at least one heteroatom selected from the group consisting of O, N, S, Si and P; Aliphatic ring groups of C ₃ -C ₂₀ ; C ₇ -C ₂₀ arylalkyl group; Arylalkenyl group of C ₈ -C ₂₀ ; -L ^a -N (R ^a ) (R ^b ); And combinations thereof may be selected from the group, and adjacent groups may combine with each other to form a ring. At this time, the ring is C ₆ ~ C ₆₀ Aromatic ring group; Fluorenyl groups; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; Aliphatic ring group of C ₃ ~ C ₆₀ ; Or it may be a fused ring group of an aromatic ring of C ₃ ~ C ₆₀ of aliphatic rings and C ₆ ~ C _60.

e 'is an integer of 0-4, f' = an integer of 0-2, g 'is an integer of 0-9, h' is an integer of 0-5, and when each of these is an integer of 2 or more, each of several R <^13> is respectively Are the same or different from each other.

Ar ^a is a C ₆ ~ C ₂₀ aryl group; Fluorenyl groups; C ₂ ~ C ₂₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; Aliphatic ring group of C ₃ ~ C ₂₀ ; And combinations thereof may be selected from the group.

L ^a , R ^a , R ^b are the same as defined in Formula 2.

Specifically, the compound represented by Formula 1 may be one of the following compounds, but is not limited thereto.

Specifically, the compound represented by Formula 2 may be one of the following compounds, but is not limited thereto.

Specifically, the compound represented by Formula 3 may be one of the following compounds, but is not limited thereto.

Preferably, the host is 40 to 80% by weight of the first compound represented by Formula 1, 10 to 30% by weight of the second compound represented by Formula 2 and 10 to 40% by weight of the third compound represented by Formula 3 Is done.

Hereinafter, the synthesis examples of the compounds represented by the formulas (1) to (3) according to the present invention and the production examples of the organic electric device will be described in detail with reference to Examples, but the present invention is not limited to the following Examples.

Synthesis Example

[ Synthesis Example  One]

The compound represented by Chemical Formula 1 according to the present invention may be prepared by reacting Sub 1 and Sub 2 as in Scheme 1 below.

<Scheme 1>

I of Sub 1 Synthesis Example

Sub 1 of Scheme 1 may be synthesized by the reaction route of Scheme 2, but is not limited thereto.

<Scheme 2>

Sub 1-16 Synthesis Example

(1) Synthesis of Sub 1-16a

5-bromobenzo [b] naphtha [1,2-d] thiophene (50 g, 159.64 mmol), bis (pinacolato) diboron (44.59 g, 175.60 mmol), KOAc (47 g, 478.91 mmol), PdCl ₂ (dppf) (3.50 g, 4.79 mmol) was dissolved in DMF (1 L) solvent and then refluxed at 120 ° C. for 12 hours. After the reaction was completed, the temperature of the reactant was cooled to room temperature, extracted with CH ₂ Cl ₂ , and washed with water. The organic layer was dried over MgSO ₄ , concentrated and recrystallized with CH ₂ Cl ₂ and methanol solvent to give the product (46.01 g, 80%).

(2) Sub 1-16b Synthesis

Sub 1-16a (45.94g, 156.17mmol), 1-bromo-2-nitrobenzene (38.90g, 156.17mmol), K ₂ CO ₃ (64.75g, 468.51mmol), Pd (PPh ₃ ) ₄ (5.41g, 4.69 mmol), THF (680mL) and water (340mL) were put into a round bottom flask, THF (600 mL) and water (300 mL) were dissolved and refluxed at 80 ° C. for 12 hours. After the reaction was completed, the temperature of the reactant was cooled to room temperature, extracted with CH ₂ Cl ₂ , and washed with water. The organic layer was dried over MgSO ₄ and concentrated. The concentrate was then separated by silica gel column to give the product (38.85 g, 70%).

(3) Sub 1-16 Synthesis

Sub 1-16b (38.85g, 109.31mmol) and triphenylphosphine (71.68g, 273.28mmol) were dissolved in o -dichlorobenzene (547mL) and refluxed at 200 ° C for 24 hours. After the reaction was completed, the solvent was removed by distillation under reduced pressure, and the concentrated product was separated by silica gel column and recrystallized to obtain the desired product (25.81 g, 73%).

2.Sub 1-17 Synthesis Example

(1) Sub 1-17 Synthesis

5-bromobenzo [b] naphtho [2,1-d] thiophene (55 g, 175.60 mmol), bis (pinacolato) diboron (49.05 g, 193.16 mmol), KOAc (51.7 g, 526.80 mmol), PdCl ₂ (dppf) ( 3.86 g, 5.27 mmol) and DMF (1.11 L) were used to carry out the same method as the synthesis method of Sub 1-16a, to obtain a product (49.35 g, 78%).

(2) Sub 1-17b Synthesis

Sub 1-17a (49.22g, 136.63mmol), 1-bromo-2-nitrobenzene (27.60g, 136.63mmol), K ₂ CO ₃ (56.65g, 409.88mmol), Pd (PPh ₃ ) ₄ (4.74g, 4.1 mmol), THF (601 mL) and water (301 mL) were used in the same manner as the Synthesis Method of Sub 1-16b to obtain a product (26.16 g, 67%).

(3) Sub 1-17 Synthesis

Sub 1-17b (26.16g, 73.61mmol), triphenylphosphine (48.26g, 184.01mmol) and o -dichlorobenzene (368mL) were used to proceed in the same manner as the synthesis method of Sub 1-16 (15.95g, 67 %) Was obtained.

3.Sub 1-22 Synthesis Example

(1) Sub 1-22a Synthesis

9-bromo-11-phenyl-11H-benzo [a] carbazole (55g, 147.74mmol), bis (pinacolato) diboron (41.27g, 162.52mmol), KOAc (43.5g, 443.23mmol), PdCl ₂ (dppf) ( 3.24 g, 4.43 mmol) was used in the same manner as the Synthesis Method of Sub 1-16a, to obtain a product (51.42 g, 83%).

(2) Sub 1-22b Synthesis

Sub 1-22a (51.42g, 122.62mmol), 1-bromo-2-nitrobenzene (24.77g, 122.62mmol), K ₂ CO ₃ (50.84g, 367.87mmol), Pd (PPh ₃ ) ₄ (4.25g, 3.68 mmol)), THF (540mL) and water (270mL) were used to perform the same method as the synthesis of Sub 1-16b, to obtain a product (38.63g, 76%).

(3) Sub 1-22 synthesis

Sub 1-22b (38.63g, 93.21mmol), triphenylphosphine (61.12g, 233.01mmol) using o -dichlorobenzene (466 mL) in the same manner as the synthesis method of Sub 1-16, the product (14.97g, 42%).

4.Sub 1-28 Synthesis Example

(1) Sub 1-28a Synthesis

11-bromophenanthro [9,10-b] benzofuran (60 g, 172.81 mmol), bis (pinacolato) diboron (48.27 g, 190.09 mmol), KOAc (50.88 g, 518.42 mmol), PdCl ₂ (dppf) (3.79 g, 5.18 mmol) was used to perform the same method as the synthesis method of Sub 1-16a, to obtain a product (52.46 g, 77%).

(2) Sub 1-28b Synthesis

Sub 1-28a (52.46g, 133.05mmol), 1-bromo-2-nitrobenzene (26.88g, 133.05mmol), K ₂ CO ₃ (55.17g, 399.16mmol), Pd (PPh ₃ ) ₄ (4.61g, 3.99 mmol), THF (574 mL) and water (287 mL) were used in the same manner as the Synthesis of Sub 1-16b to obtain a product (40.93 g, 79%).

(3) Sub 1-28 synthesis

Sub 1-28b (40.93g, 105.11mmol), triphenylphosphine (68.92g, 262.77mmol), o -dichlorobenzene (526mL) was carried out in the same manner as the experimental method of Sub 1-1 to the product Sub 1-28 (15.03g, 40%).

5.Sub 1-41 Synthesis Example

(1) Sub 1-41a synthesis

2-bromo-11,11-dimethyl-11H-benzo [b] fluorene (60g, 185.63mmol), bis (pinacolato) diboron (51.85g, 204.19mmol), KOAc (54.65g, 556.88mmol), PdCl ₂ (dppf ) (4.08g, 5.57mmol) was used in the same manner as the Synthesis Method of Sub 1-16a to obtain a product (50.87g, 74%).

(2) Sub 1-41b Synthesis

Sub 1-41a (50.87 g, 137.38 mmol), 2-bromo-1-nitronaphthalene (34.63 g, 137.38 mmol), K ₂ CO ₃ (56.96 g, 412.13 mmol), Pd (PPh ₃ ) ₄ (4.76 g, 4.12 mmol), THF (568 mL) and water (284 mL) were used in the same manner as the Synthesis of Sub 1-16b to obtain a product (45.09 g, 79%).

(3) Sub 1-41 Synthesis

Sub 1-41b (45.09g, 108.52mmol) and triphenylphosphine (71.16g, 271.31mmol) were proceeded in the same manner as the synthesis method of Sub 1-16 using o -dichlorobenzene (543mL) to give a product (15.81g, 38 %) Was obtained.

6.Sub 1-50 Synthesis Example

(1) Synthesis of Sub 1-50a

9-bromo-7-phenyl-7H-benzo [c] carbazole (60g, 161.17mmol), bis (pinacolato) diboron (45.02g, 177.29mmol), KOAc (47.45g, 483.52mmol), PdCl ₂ (dppf) ( 3.54 g, 4.84 mmol) was used in the same manner as the Synthesis Method of Sub 1-16a, to obtain a product (52.04 g, 77%).

(2) Sub 1-50b Synthesis

Sub 1-50a (52.04g, 124.10mmol), 2-bromo-3-nitronaphthalene (31.28g, 124.10mmol), K ₂ CO ₃ (51.46g, 372.31mmol), Pd (PPh ₃ ) ₄ (4.30g, 3.72 mmol), THF (546 mL) and water (273 mL) were used in the same manner as the Synthesis of Sub 1-16b, to obtain a product (45.54 g, 79%).

(3) Sub 1-50 synthesis

Sub 1-50b (45.54g, 98.04mmol), triphenylphosphine (64.29g, 245.09mmol), o -dichlorobenzene (490mL) was carried out by the same method as the synthesis method of Sub 1-16 (16.96g, 40 %) Was obtained.

7.Sub 1-56 Synthesis Example

(1) Synthesis of Sub 1-56a

2-bromonaphtho [2,3-b] benzofuran (60 g, 201.92 mmol), bis (pinacolato) diboron (56.40 g, 222.11 mmol), KOAc (59.45 g, 605.75 mmol), PdCl ₂ (dppf) (4.43 g, 6.06 mmol) to proceed to the same method as the synthesis of Sub 1-16a, to obtain a product (55.60g, 80%).

(2) Sub 1-56b Synthesis

Sub 1-56a (55.60g, 161.52mmol), 1-bromo-2-nitronaphthalene (40.72g, 161.52mmol), K ₂ CO ₃ (66.97g, 484.57mmol), Pd (PPh ₃ ) ₄ (5.60g, 4.85 mmol), THF (711 mL) and water (355 mL) were used in the same manner as the Synthesis of Sub 1-16b to obtain a product (45.55 g, 74%).

(3) Sub 1-56 Synthesis

Sub 1-56b (45.55g, 116.97mmol), triphenylphosphine (76.7g, 292.43mmol), o -dichlorobenzene (585 mL) was carried out in the same manner as the synthesis method of Sub 1-16 to give a product (15.89g, 38%).

8.Sub 1-81 Synthesis Example

(1) Sub 1-76a synthesis

5-bromodinaphtho [1,2-b: 2 ', 1'-d] furan (60 g, 172.81 mmol), bis (pinacolato) diboron (48.27 g, 190.09 mmol), KOAc (50.88 g, 518.42 mmol), PdCl ₂ (dppf) (3.79 g, 5.18 mmol) was used in the same manner as the Synthesis Method of Sub 1-16a, to obtain a product (52.46 g, 77%).

(2) Sub 1-76b Synthesis

Sub 1-76a (52.46 g, 133.05 mmol), 1-bromo-2-nitronaphthalene (33.54 g, 133.05 mmol), K ₂ CO ₃ (55.17 g, 399.16 mmol), Pd (PPh ₃ ) ₄ (4.61 g, 3.99 mmol), THF (585mL) and water (293mL) were used to perform the same method as the synthesis method of Sub 1-16b to obtain a product (40.93g, 70%).

(3) Sub 1-76 Synthesis

Sub 1-76b (40.93g, 93.13mmol), triphenylphosphine (61.07g, 232.84mmol), o -dichlorobenzene (466mL) using the same method as the synthesis method of Sub 1-16 The product (23.15g, 61 %) Was obtained.

9.Sub 1-82 Synthesis Example

(1) Synthesis of Sub 1-82a

11-bromo-13,13-dimethyl-13H-indeno [1,2-l] phenanthrene (60 g, 219.64 mmol), bis (pinacolato) diboron (61.35 g, 241.61 mmol), KOAc (64.67 g, 658.93 mmol), PdCl ₂ (dppf) (4.82 g, 6.59 mmol) was used in the same manner as the synthesis of Sub 1-16a to obtain (52.05 g, 74%).

(2) Sub 1-82b Synthesis

Sub 1-82a (52.05g, 162.53mmol), 1-bromo-2-nitrobenzene (49.11g, 162.53mmol), K ₂ CO ₃ (67.39g, 487.60mmol), Pd (PPh ₃ ) ₄ (5.63g, 4.88 mmol), THF (715ml) and water (358ml) were used in the same manner as the Synthesis of Sub 1-16b to obtain a product (47.95, 71%).

(3) Sub 1-82 Synthesis

Sub 1-82b (47.95g, 115.41mmol), triphenylphosphine (75.67g, 288.51mmol) and o -dichlorobenzene (577mL) were used to proceed in the same manner as the synthesis method of Sub 1-16 (18.59g, 42 %) Was obtained.

10.Sub 1-93 Synthesis Example

(1) Sub 1-93a synthesis

3-bromo-9,9-dimethyl-9H-fluorene (60g, 219.64mmol), bis (pinacolato) diboron (61.35g, 241.61mmol), KOAc (64.67g, 658.93mmol), PdCl ₂ (dppf) (4.82g , 6.59 mmol) was obtained in the same manner as the synthesis method of Sub 1-16a to obtain (52.05 g, 74%).

(2) Sub 1-93b Synthesis

Sub 1-93a (52.05g, 162.53mmol), 9-bromo-10-nitrophenanthrene (49.11g, 162.53mmol), K ₂ CO ₃ (67.39g, 487.60mmol), Pd (PPh ₃ ) ₄ (5.63g, 4.88 mmol), THF (715ml) and water (358ml) were used in the same manner as the Synthesis of Sub 1-16b to obtain a product (47.95, 71%).

(3) Sub 1-93 Synthesis

Sub 1-93b (47.95g, 115.41mmol), triphenylphosphine (75.67g, 288.51mmol) and o -dichlorobenzene (577mL) were used to proceed in the same manner as the synthesis method of Sub 1-16 (18.59g, 42 %) Was obtained.

11.Sub 1-94 Synthesis Example

(1) Sub 1-94b Synthesis

Sub 1-94a (40g, 111.02mmol), 3-bromo-4-nitro-1,1'-biphenyl (30.88g, 111.02mmol), K ₂ CO ₃ (46.03g, 333.07mmol), Pd (PPh ₃ ) ₄ (3.85g, 3.33mmol), THF (489ml) and water (244ml) were used in the same manner as the synthesis of Sub 1-16b to obtain the product (34.97, 73%).

(2) Sub 1-94 Synthesis

Sub 1-94b (34.97g, 81.04mmol), triphenylphosphine (53.14g, 202.60mmol) and o -dichlorobenzene (405mL) were used to proceed in the same manner as the synthesis method of Sub 1-16 (21.69g, 67 %) Was obtained.

12.Sub 1-97 Synthesis Example

(1) Sub 1-97b Synthesis

Sub 1-97a (40 g, 111.02 mmol), 3- (4-bromo-3-nitrophenyl) -9-phenyl-9H-carbazole (49.22 g, 111.02 mmol), K ₂ CO ₃ (46.03 g, 333.07 mmol), Pd (PPh ₃ ) ₄ (3.85g, 3.33mmol), THF (489ml) and water (244ml) were used to carry out the same method as the synthesis of Sub 1-16b, to obtain a product (42.40, 64%).

(2) Sub 1-97 Synthesis

Sub 1-97b (42.40g, 71.06mmol), triphenylphosphine (46.59g, 177.64mmol) and o -dichlorobenzene (355mL) were used in the same manner as the synthesis method of Sub 1-16 to obtain the product (24.48g, 61 %) Was obtained.

13.Sub 1-103 Synthesis Example

(1) Sub 1-103b Synthesis

Sub 1-103a (57.17g, 158.69mmol), 2-bromo-1-nitronaphthalene (40g, 158.69mmol), K ₂ CO ₃ (65.80g, 476.06mmol), Pd (PPh ₃ ) ₄ (5.50g, 4.76mmol ), THF (698ml) and water (349ml) were used in the same manner as the Synthesis of Sub 1-16b to obtain a product (47.61, 74%).

(2) Sub 1-103 Synthesis

Sub 1-103b (47.61g, 117.42mmol), triphenylphosphine (76.99g, 293.55mmol), o -dichlorobenzene (587mL) was used to proceed in the same manner as the synthesis method of Sub 1-16 (28.07g, 64 %) Was obtained.

Compounds belonging to Sub 1 are the same as the following compounds, but are not limited thereto, and Table 1 shows FD-MS (Field Desorption-Mass Spectrometry) values of these compounds.

TABLE 1

Ⅱ. Of Sub 2 Synthesis Example

Sub 2 of Scheme 1 may be synthesized by the reaction route of Scheme 3, but is not limited thereto.

Scheme 3 (Hal ¹ is I, Br or Cl, Hal ² is Br or Cl)

Sub 2-35 Synthesis Example

(1) Sub 2-35a Synthesis

1-amino-2-naphthoic acid (CAS Registry Number: 4919-43-1) (75.11 g, 401.25 mmol) was added to a urea (CAS Registry Number: 57-13-6) (168.69 g, 2808.75 mmol) in a round bottom flask. Was added together and stirred at 160 ° C. After confirming the reaction by TLC, it was cooled to 100 ℃ and water (200ml) was added and stirred for 1 hour. When the reaction was completed, the resulting solid was filtered under reduced pressure, washed with water and dried to give 63.86 g (yield: 75%) of the product.

(2) Sub 2-35b Synthesis

Sub 2-35a (63.86 g, 300.94 mmol) was dissolved in POCl ₃ (200 ml) at room temperature, and N , N- Diisopropylethylamine (97.23 g, 752.36 mmol) was slowly added dropwise and stirred at 90 ° C. When the reaction was completed, the product was concentrated, ice water (500ml) was added and stirred at room temperature for 1 hour. The resulting solid was filtered under reduced pressure and dried to give 67.47 g (yield: 90%) of product.

(3) Sub 2-35 synthesis

Sub 2-35b (67.47 g, 270.86 mmol) was added to a round-bottomed flask and dissolved in THF (950 ml). 4,4,5,5-tetramethyl-2-phenyl-1,3,2-dioxaborolane (CAS Registry Number) : 24388-23-6) (60.80 g, 297.94 mmol), Pd (PPh ₃ ) ₄ (12.52 g, 10.83 mmol), K ₂ CO ₃ (112.30 g, 812.57 mmol), water (475 ml) were added and stirred at 90 ° C. After completion of the reaction, the mixture was extracted with CH ₂ Cl ₂ and water, and the organic layer was dried over MgSO ₄ and concentrated. The concentrate was then separated by silica gel column and recrystallized to give 44.89 g (yield: 57%) of product.

2.Sub 2-40 Synthesis Example

Sub 2-40b (19g, 76.28mmol), 2- (dibenzo [b, d] furan-2-yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane (CAS Registry Number: 947770-80-1) (22.44 g, 76.28 mmol), Pd (PPh ₃ ) ₄ (1.32 g, 1.14 mmol), K ₂ CO ₃ (15.81 g, 114.42 mmol), THF (336 ml), and water (168 ml) were added, followed by the same method as the synthesis method of Sub 2-35, to obtain 15.69 g of the product. (Yield 54%) was obtained.

3.Sub 2-43 Synthesis Example

2,4-dichlorobenzo [4,5] thieno [3,2- d ] pyrimidine (CAS Registry Number: 160199-05-3) (32.01 g, 125.47 mmol) to 4,4,5,5-tetramethyl-2- (naphthalen-1-yl) -1,3,2-dioxaborolane (CAS Registry Number: 68716-52-9) (35.07 g, 138.02 mmol), Pd (PPh ₃ ) ₄ (5.80 g, 5.02 mmol), K ₂ CO ₃ (52.02 g, 376.41 mmol), THF (440 ml), water (220 ml) were added and the procedure was carried out in the same manner as in the above Sub 2-35 synthesis to yield 19.58 g of the product (yield: 45%).

Compounds belonging to Sub 2 may be, but are not limited to, the following compounds. Table 2 shows FD-MS values of the following compounds.

TABLE 2

III. Compound of Formula 1 Synthesis Example

1.2-1 Synthesis Example

Sub 1-22 (11g, 28.76mmol), Toluene (300 mL), Sub 2-1 (4.52g, 28.76mmol), Pd ₂ (dba) ₃ (0.79g, 0.86mmol), P ( t -Bu) ₃ (0.35 g, 1.73 mmol) and NaO t -Bu (8.29 g, 86.28 mmol) were reacted in the same manner as in the synthesis of 1-1 to obtain 9.50 g (yield: 72%) of the product.

2. 1-26 Synthesis Example

Sub 1-16 (15.3 g, 47.3 mmol), Toluene (500 mL), Sub 2-28 (14.8 g, 52.0 mmol), Pd ₂ (dba) ₃ (1.3 g, 1.42 mmol), P ( t -Bu) ₃ (0.57 g, 2.84 mmol) and NaO t -Bu (13.64 g, 141.93 mmol) were reacted in the same manner as in the synthesis of 1-1, to obtain 18.97 g (yield: 72%) of product.

3. 1-27 Synthesis Example

Sub 1-16 (10 g, 30.92 mmol), Toluene (325 mL), Sub 2-42 (10.0 g, 34.01 mmol), Pd ₂ (dba) ₃ (0.85 g, 0.93 mmol), P ( t -Bu) ₃ ( 0.38 g, 1.86 mmol) and NaO t -Bu (8.91 g, 92.76 mmol) were reacted in the same manner as in the synthesis of 1-1 to obtain 12.81 g (yield: 71%) of the product.

4. 1-28 Synthesis Example

Sub 1-16 (10 g, 30.92 mmol), Toluene (325 mL), Sub 2-35 (9.89 g, 34.01 mmol), Pd ₂ (dba) ₃ (0.85 g, 0.93 mmol), P ( t -Bu) ₃ (0.38 g, 1.86 mmol) and NaO t -Bu (8.91 g, 92.76 mmol) were reacted in the same manner as in the synthesis of 1-1 to obtain 13.04 g (yield: 73%) of the product.

5. 1-31 Synthesis Example

Sub 1-28 (10g, 27.98mmol), Toluene (294mL), Sub 2-6 (9.52g, 30.78mmol), Pd ₂ (dba) ₃ (0.77g, 0.84mmol), P ( t -Bu) ₃ ( 0.34 g, 1.68 mmol) and NaO t -Bu (8.07 g, 83.94 mmol) were reacted in the same manner as in the synthesis of 1-1 to obtain 12.45 g (yield: 76%) of the product.

6. 1-36 Synthesis Example

Sub 1-32 (10g, 26.08mmol), Toluene (274mL), Sub 2-10 (9.24g, 28.68mmol), Pd ₂ (dba) ₃ (0.72g, 0.78mmol), P ( t -Bu) ₃ ( 0.32 g, 1.56 mmol) and NaO t -Bu (7.52 g, 78.23 mmol) were reacted in the same manner as in the synthesis of 1-1 to obtain 11.08 g (yield: 68%) of the product.

7. 1-67 Synthesis Example

Sub 1-56 (10 g, 27.98 mmol), Toluene (294 mL), Sub 2-47 (8.64 g, 30.78 mmol), Pd ₂ (dba) ₃ (0.77 g, 0.84 mmol), P ( t -Bu) ₃ ( 0.34 g, 1.68 mmol) and NaO t -Bu (8.07 g, 83.94 mmol) were reacted in the same manner as in the synthesis of 1-1 to obtain 11.45 g (yield: 68%) of the product.

8. 1-72 Synthesis Example

Sub 1-56 (10 g, 29.99 mmol), Toluene (500 mL), Sub 2-24 (12.78 g, 32.99 mmol), Pd ₂ (dba) ₃ (0.82 g, 0.90 mmol), P ( t -Bu) ₃ (0.36 g, 1.80 mmol) and NaO t -Bu (8.65 g, 89.97 mmol) were reacted in the same manner as in the synthesis method 1-1, to obtain 13.82 g (yield: 72%) of the product.

9. Synthesis Example 1-90

Sub 1-91 (10 g, 26.78 mmol), Toluene (281 mL), Sub 2-36 (10.04 g, 29.45 mmol), Pd ₂ (dba) ₃ (0.74 g, 0.80 mmol), P ( t -Bu) ₃ ( 0.33 g, 1.61 mmol) and NaO t -Bu (7.72 g, 80.33 mmol) were reacted in the same manner as in the synthesis of 1-1 to obtain 12.16 g (yield: 67%) of the product.

10. 1-112 Synthesis Example

Sub 1-103 (10 g, 26.78 mmol), Toluene (281 mL), Sub 2-55 (9.67 g, 26.78 mmol), Pd ₂ (dba) ₃ (0.37 g, 0.40 mmol), P ( t -Bu) ₃ ( 0.16 g, 0.80 mmol) and NaO t -Bu (3.86 g, 40.16 mmol) were reacted in the same manner as in the synthesis of 1-1 to obtain 12.25 g (yield: 70%) of the product.

The FD-MS values of the compounds 1-1 to 1-120 synthesized by the above synthesis method are shown in Table 3 below.

TABLE 3

[ Synthesis Example  2]

The compound represented by Chemical Formula 2 is synthesized by reacting Sub 3 and Sub 4 as in Scheme 4, but is not limited thereto.

Scheme 4 (Hal ³ is Br or Cl)

I. Synthesis of Sub 3

Sub 3 of Scheme 4 is synthesized by the reaction route of Scheme 5, but is not limited thereto.

Scheme 5 (Hal ⁴ is Br or Cl, Hal ⁵ is I, Br or Cl)

1.Synthesis Example of Sub 3-7

(1) Synthesis of Sub3-a-1

3-bromo-9-phenyl-9H-Carbazole (50.0 g, 155 mmol) was added to a round bottom flask and dissolved in DMF, Bis (pinacolato) diboron (43.3 g, 171 mmol), PdCl ₂ (dppf) (3.40 g , 4.65 mmol) and KOAc (64.3 g, 465 mmol) were added followed by stirring at 90 ° C. When the reaction was completed, the DMF was removed by distillation, and extracted with CH ₂ Cl ₂ and water. The organic layer was dried over MgSO ₄ , concentrated, and the concentrate was separated with silica gel column and recrystallized to give 41.8 g (yield: 73%) of product.

(2) Synthesis of Sub3-7

Sub3-a-1 (41.8 g, 113 mmol) was added to a round-bottom flask and dissolved in THF, followed by 3-bromo-9H-carbazole (27.8 g, 113 mmol), Pd (PPh ₃ ) ₄ (7.83 g, 6.78 mmol ), K ₂ CO ₃ (2.74 g, 13.6 mmol), water were added and stirred at 80 ° C. After completion of the reaction, the mixture was extracted with CH ₂ Cl ₂ and water, and the organic layer was dried over MgSO ₄ and concentrated. Thereafter, the silica gel column was separated and recrystallized to obtain 37.9 g (yield: 82%) of the product.

2.Sub 3-16 Synthesis Example

(1) Synthesis of Sub3-a-2

Naphthalen-1-ylboronic acid (30.0 g, 174 mmol), 4-bromo-2-iodo-1-nitrobenzene (57.2 g, 174 mmol), Pd (PPh ₃ ) ₄ (12.1 g, 10.5 mmol), K ₂ CO ₃ (72.3 g, 523 mmol) was used to proceed in the same manner as the synthesis of Sub3-7 to obtain 44.6 g (yield: 78%) of product.

(2) Synthesis of Sub3-a-3

Sub3-a-2 (44.6 g, 136 mmol) was dissolved in o -dichlorobenzene (350mL), triphenylphosphine (89.2 g, 340 mmol) was added and stirred at 200 ^° C. After the reaction was completed, o -dichlorobenzene was removed by distillation and extracted with CH ₂ Cl ₂ and water. The organic layer was dried over MgSO ₄ , concentrated, separated by silica gel column and recrystallized to give 33.4 g (yield: 83%) of product.

(3) Synthesis of Sub3-16

Sub3-a-3 (33.4 g, 113 mmol), Sub3-a-1 (41.7 g, 113 mmol), Pd (PPh ₃ ) ₄ (7.83 g, 6.78 mmol), K ₂ CO ₃ (46.8 g, 339 mmol In the same manner as in the synthesis of Sub3-7, the product 40.9 g (yield: 79%) was obtained.

3. Sub 3-26 Synthesis Example

(1) Synthesis of Sub3-a-4

2-bromodibenzo [b, d] thiophene (50.0 g, 190 mmol), Bis (pinacolato) diboron (53.7 g, 209 mmol), PdCl ₂ (dppf) (4.17 g, 5.70 mmol), KOAc (55.9 g, 570 mmol In the same manner as in the synthesis of Sub3-a-1, the product 41.8 g (yield: 71%) was obtained.

(2) Synthesis of Sub3-26

Sub3-a-4 (41.8 g, 135 mmol), Sub3-a-3 (40.0 g, 135 mmol), Pd (PPh ₃ ) ₄ (9.36 g, 8.10 mmol), K ₂ CO ₃ (56.0 g, 405 mmol ) In the same manner as in the synthesis of Sub3-7 to give 44.2 g (yield: 82%) of the product.

4.Sub 3-33 Synthesis Example

(1) Synthesis of Sub3-a-5

2-bromodibenzo [b, d] thiophene (60.0 g, 228 mmol), (2-nitrophenyl) boronic acid (38.1 g, 228 mmol), Pd (PPh ₃ ) ₄ (15.8 g, 13.7 mmol), K ₂ CO ₃ (94.5 g, 684 mmol) was used in the same manner as the Synthesis of Sub3-7 to obtain 58.5 g (yield: 84%) of product.

(2) Synthesis of Sub3-a-6

Sub3-a-5 (58.5 g, 192 mmol) and triphenylphosphine (126 g, 479 mmol) were used in the same manner as in the synthesis of Sub3-a-3, to obtain 45.0 g (yield: 86%) of the product.

(3) Synthesis of Sub3-a-7

Sub3-a-6 (45.0 g, 165 mmol), N-Bromosuccinimide (29.3 g, 165mmol) and Methylene chloride (350mL) were added to a round bottom flask and stirred at room temperature for 4 hours. After the reaction is completed, distilled water is added and extracted with Methylene chloride and water. The organic layer was dried over MgSO ₄ , concentrated, and the concentrate was recrystallized with Methylene chloride and Hexane to give the product 41.8 g (72% yield).

(4) Synthesis of Sub3-33

Sub3-a-1 (43.8 g, 119 mmol), Sub3-a-7 (41.8 g, 119 mmol), Pd (PPh ₃ ) ₄ (8.22 g, 7.12 mmol), K ₂ CO ₃ (49.2 g, 356 mmol In the same manner as in the synthesis of Sub3-7, the product 50.0 g (yield: 82%) was obtained.

5. Sub 3-36 Synthesis Example

(1) Synthesis of Sub3-a-8

1,4-dibromo-9-phenyl-9H-carbazole (50.0 g, 125 mmol) was added to a round bottom flask and dissolved with toluene (500 mL), 2-chloroaniline (15.9 g, 125 mmol), Pd ₂ (dba ) ₃ (3.42 g, 3.74 mmol), P ( t -Bu) ₃ (1.51 g, 7.48 mmol), NaO t -Bu (24.0 g, 249 mmol) were added and stirred at 120 ° C. After completion of the reaction, the mixture was extracted with CH ₂ Cl ₂ and water, and the organic layer was dried over MgSO ₄ and concentrated. The concentrate was then separated by silica gel column and recrystallized to give 43.0 g (yield: 77%) of product.

(2) Synthesis of Sub3-a-9

Sub3-a-8 (43.0 g, 96.0 mmol) and triphenylphosphine (62.9 g, 240 mmol) were used in the same manner as the synthesis of Sub3-a-3, to obtain 32.0 g (yield: 81%) of the product.

(3) Synthesis of Sub3-36

Sub3-a-9 (32.0 g, 77.7 mmol), Sub3-a-10 (28.7 g, 77.7 mmol), Pd (PPh ₃ ) ₄ (5.39 g, 4.66 mmol), K ₂ CO ₃ (32.2 g, 233 mmol ) Was proceeded in the same manner as in the synthesis of Sub3-7 to obtain 33.4 g (yield: 75%) of product.

6.Sub 3-40 Synthesis Example

(1) Synthesis of Sub3-a-11

Dibenzo [b, d] thiophen-3-ylboronic acid (50.0 g, 219 mmol), 4-bromo-2-iodo-1-nitrobenzene (71.9 g, 219 mmol), Pd (PPh ₃ ) ₄ (15.2g, 13.2 mmol), K ₂ CO ₃ (90.8 g, 657 mmol) was used in the same manner as the synthesis of Sub3-7 to obtain 64.0 g (yield: 76%) of product.

(2) Synthesis of Sub3-a-12

Sub3-a-11 (64.0 g, 166 mmol) and triphenylphosphine (10.9 g, 416 mmol) were used in the same manner as the synthesis of Sub3-a-3, to obtain 46.9 g (yield: 80%) of the product.

(3) Synthesis of Sub3-40

Sub3-a-12 (46.9 g, 133 mmol), Sub3-a-10 (49.3 g, 133 mmol), Pd (PPh ₃ ) ₄ (9.25 g, 8.01 mmol), K ₂ CO ₃ (55.3 g, 400 mmol ), The process was carried out in the same manner as the synthesis of Sub3-7 to obtain 58.4 g (yield 85%) of the product.

7.Sub 3-74 Synthesis Example

(1) Synthesis of Sub3-a-14

Naphthalene-1-ylboronic acid (34.0 g, 198 mmol), 1-bromo-2-nitronaphthalene (49.8g, 198 mmol), Pd (PPh ₃ ) ₄ (1.37 g, 11.9 mmol), K ₂ CO ₃ (82.0 g , 593 mmol) was used in the same manner as the Synthesis of Sub3-7 to obtain 51.0 g (yield: 86%) of the product.

(2) Synthesis of Sub3-74

Sub3-a-13 (51.0 g, 170 mmol) and triphenylphosphine (111 g, 425 mmol) were used in the same manner as the synthesis of Sub3-a-3, to obtain 31.8 g (yield: 70%) of the product.

Compounds belonging to Sub 3 may be, but are not limited to, the following compounds. Table 4 shows FD-MS values of the following compounds.

TABLE 4

II. Synthesis of Sub 4

Compounds belonging to Sub 4 may be the following compounds, but are not limited thereto, and Table 5 shows FD-MS values of the following compounds.

TABLE 5

III. Synthesis of Compound of Formula 2

1.2-30 Synthesis Example

Sub 3-7 (37.9 g, 92.8 mmol ) were placed in a round bottom flask was dissolved in Toluene (400ml), Sub 2-4 ( 21.6 g, 92.8 mmol), Pd 2 (dba) 3 (2.55 g, 2.78 mmol) , P ( t -Bu) ₃ (1.13 g, 5.57 mmol), NaO t -Bu (17.8 g, 186 mmol) was added and stirred at 100 ° C. After completion of the reaction, the mixture was extracted with CH ₂ Cl ₂ and water, and the organic layer was dried over MgSO ₄ and concentrated. Thereafter, the concentrate was separated with a silica gel column and recrystallized to obtain 45.8 g (yield: 88%) of the product.

2. 2-49 Synthesis Example

Sub 3-16 (40.9 g, 89.2 mmol), Sub 2-4 (20.8 g, 89.2 mmol), Pd ₂ (dba) ₃ (2.45 g, 2.68 mmol), P ( t -Bu) ₃ (1.08 g, 5.35 mmol), NaO t -Bu (17.1 g, 178 mmol) was used in the same manner as in the synthesis of 2-30, to obtain 45.8 g (yield: 84%) of the product.

3. 2-59 Synthesis Example

Sub 3-26 (44.2 g, 111 mmol), Sub 2-5 (25.8 g, 111 mmol), Pd ₂ (dba) ₃ (3.04 g, 3.32 mmol), P ( t -Bu) ₃ (1.34 g, 6.64 mmol), NaO t -Bu (21.3 g, 221 mmol) was used in the same manner as in the synthesis method of 2-30, to obtain 52.5 g (yield: 86%) of the product.

4. 2-66 Synthesis Example

Sub 3-33 (50.0 g, 97.2 mmol), Sub 6-92 (37.7 g, 97.2 mmol), Pd ₂ (dba) ₃ (2.67 g, 2.92 mmol), P ( t -Bu) ₃ (1.18 g, 5.83 mmol), NaO t -Bu (18.7 g, 194 mmol) was used in the same manner as the synthesis method of 2-30 to obtain 62.3 g (yield: 78%) of the product.

5. 2-69 Synthesis Example

Sub 3-36 (33.4 g, 58.2 mmol), Sub 2-5 (13.6 g, 58.2 mmol), Pd ₂ (dba) ₃ (1.60 g, 1.75 mmol), P ( t -Bu) ₃ (0.71 g, 3.49 mmol), NaO t -Bu (11.2 g, 116 mmol) was used in the same manner as the synthesis method of 2-30 to obtain 37.2 g (yield 88%) of product.

6. 2-73 Synthesis Example

Sub 3-40 (58.4 g, 113 mmol), Sub 6-88 (32.2 g, 113 mmol), Pd ₂ (dba) ₃ (3.12 g, 3.40 mmol), P ( t -Bu) ₃ (13.8 g, 6.81 mmol), NaO t -Bu (21.8 g, 227 mmol) was carried out in the same manner as the synthesis method of 2-30 to obtain 66.0 g (yield 81%) of the product.

7. 3-108 Synthesis Example

Sub 3-74 (31.8 g, 119 mmol), Sub 2-6 (36.8 g, 119 mmol), Pd ₂ (dba) ₃ (3.27 g, 3.57 mmol), P ( t -Bu) ₃ (1.44 g, 7.14 mmol) and NaO t -Bu (22.9 g, 238 mmol) were used in the same manner as in the synthesis of 2-30, to obtain 53.1 g (yield 90%) of product.

The FD-MS values of the compounds 2-1 to 2-160 prepared according to the synthesis example described above are shown in Table 6 below.

TABLE 6

[ Synthesis Example  3]

The compound represented by Formula 3 may be synthesized as in Scheme 6, but is not limited thereto.

Scheme 6 (Hal ¹ and Hal ² are I, Br or Cl)

I. of Sub 5 Synthesis Example

Synthesis examples of the compound belonging to Sub 5 of Scheme 6 are as follows.

1.Sub 5-1 Synthesis Example

2-([1,1'-biphenyl] -4-yl) -4,6-dichloro-1,3,5-triazine (CAS Registry Number: 10202-45-6) (20 g, 66.19 mmol) and 4 -Biphenylboronic acid (CAS Registry Number: 5122-94-1) (13.1 g, 66.19 mmol) is added to a round bottom flask and dissolved in THF (370 ml). Then Pd (PPh ₃ ) ₄ (3.8 g, 3.31 mmol), K ₂ CO ₃ (27.4 g, 198.57 mmol), and water (165 ml) are added and stirred to reflux. When the reaction is complete, the mixture is extracted with ether and water, and then the organic layer is concentrated. The concentrated organic layer was dried over MgSO ₄ , concentrated once more, separated with silica gel column and recrystallized to give 20.8 g of product. (75% yield)

2. Sub 5-8 Synthesis Example

2,4-dichloro-6- (naphthalen-2-yl) -1,3,5-triazine (20 g, 72.43 mmol), (3- (pyridin-2-yl) phenyl) boronic acid (14.3 g, 72.43 mmol), Pd (PPh ₃ ) ₄ (0.05 equiv), K ₂ CO ₃ (3 equiv), anhydrous THF and water were carried out in the same manner as in the Sub 5-1 synthesis to obtain 20.3 g of the product. (71% yield)

3. Synthesis Example of Sub 5-19

2-([1,1'-biphenyl] -4-yl) -4,6-dichloro-1,3,5-triazine (15 g, 49.64 mmol), (9,9-dimethyl-9H-fluoren-3 -yl) boronic acid (11.8 g, 49.64 mmol), Pd (PPh ₃ ) ₄ (0.05 equiv), K ₂ CO ₃ (3 equiv), anhydrous THF and water in the same manner as in Sub 5-1 It progressed and obtained 15.7 g of products. (Yield 69%)

4.Sub 5-19 Synthesis Example

2,4-dichloro-6-phenyl-1,3,5-triazine (30 g, 132.71 mmol), dibenzo [b, d] furan-2-ylboronic acid (28.1 g, 132.71 mmol), Pd (PPh ₃ ) ₄ (0.05 equiv), K ₂ CO ₃ (3 equiv), anhydrous THF and water were used in the same manner as in the Sub 5-1 synthesis to obtain 30.8 g of product. (Yield 65%)

Compounds belonging to Sub 5 may be the following compounds, but are not limited thereto, and Table 7 shows FD-MS values of the following compounds.

 TABLE 7

II. Of Sub 6 Synthesis Example

Sub 6 of Scheme 6 may be synthesized by the following Scheme 7, but is not limited thereto.

Scheme 7 (Hal ³ is I, Br or Cl, L is L ⁵ or L ⁶ and Ar is Ar ⁷ or Ar ⁸ )

1.Sub 6-2 Synthesis Example

4-bromo-1,1'-biphenyl (5 g, 21.45 mmol) was dissolved in DMF (270 ml), followed by bis (pinacolato) diboron (7.1 g, 27.89 mmol), PdCl ₂ (dppf) _, (0.78 g, 1.07 mmol), KOAc (6.3 g, 64.35 mmol) and DMF (270 ml) were added thereto, and the mixture was stirred and refluxed at 120 ° C. After the reaction is completed, the temperature of the reactant is cooled to room temperature, extracted with MC and wiped with water. The organic layer is dried over MgSO ₄ and concentrated. The concentrate was then separated by silica gel column to give 3.4 g (80%) of product.

2. Synthesis Example of Sub 6-37

2-bromodibenzo [b, d] furan (10 g, 40.47 mmol) was dissolved in anhydrous DMF, followed by bis (pinacolato) diboron (13.3 g, 52.61 mmol), PdCl ₂ (dppf) _, (0.05 equiv), KOAc (3 Equivalent)) and stirred at reflux at 120 ° C. After the reaction is completed, the temperature of the reactant is cooled to room temperature, extracted with MC and wiped with water. The organic layer is dried over MgSO ₄ and concentrated. The concentrate was then separated by silica gel column to synthesize 7 g of product product. (Yield 82%)

Compounds belonging to Sub 6 may be the following compounds, but are not limited thereto, and Table 8 shows FD-MS values of the following compounds.

TABLE 8

III. Synthesis of Compound of Formula 3

1. Synthesis Example of 3-15

Sub 5-1 (5 g, 11.91 mmol) and Sub 6-44 (4 g, 13.1 mmol) are added to a round bottom flask and dissolved in THF (70 ml). Then Pd (PPh ₃ ) ₄ (0.7 g, 0.6 mmol), K ₂ CO ₃ (5 g, 35.73 mmol) and water (30 ml) are added and stirred to reflux. When the reaction is complete, the mixture is extracted with ether and water, and then the organic layer is concentrated. The concentrated organic layer is dried over MgSO ₄ and concentrated once more. The final concentrate was separated using silica gel column and then recrystallized to give 5.4 g of product. (71% yield)

2. Synthesis Example of 3-55

Using Sub 5-29 (4 g, 14.94 mmol), Sub 6-45 (9.5 g, 16.43 mmol), Pd (PPh ₃ ) ₄ (0.05 equiv), K ₂ CO ₃ (3 equiv), anhydrous THF and water 8.8 g of the product was synthesized in the same manner as in the 3-15 synthesis method. (Yield 77%)

3. Synthesis Example of 3-96

Using Sub 5-29 (4 g, 14.94 mmol), Sub 6-47 (7 g, 16.43 mmol), Pd (PPh ₃ ) ₄ (0.05 equiv), K ₂ CO ₃ (3 equiv), anhydrous THF and water 6 g of the product was synthesized by the same method as in the above 3-15 synthesis method. (66% yield)

4. Synthesis Example of 3-106

2,4-dichloro-6-phenyl-1,3,5-triazine (7 g, 30.97 mmol), Sub 6-47 (13.1 g, 61.94 mmol), Pd (PPh ₃ ) ₄ (0.1 equiv), K ₂ 9.7 g of product was synthesized using CO ₃ (6 equiv), anhydrous THF and water in the same manner as in the above 3-15 synthesis. (64% yield)

5. Synthesis Example of 3-111

Using Sub 5-29 (4 g, 14.94 mmol), Sub 6-41 (7.3 g, 16.43 mmol), Pd (PPh ₃ ) ₄ (0.05 equiv), K ₂ CO ₃ (3 equiv), anhydrous THF and water 7 g of the product was synthesized by the same method as in the above 3-15 synthesis method. (75% yield)

The FD-MS values of the compounds 3-1 to 3-116 synthesized by the above synthesis method are shown in Table 9 below.

TABLE 9

Manufacturing Evaluation of Organic Electrical Device

Example 1 Red Organic Light Emitting Diode (Mixed Phosphorescent Host)

A 4,4 ', 4 "-Tris [2-naphthyl (phenyl) amino] triphenylamine (hereinafter abbreviated as 2-TNATA) film is vacuum deposited on the ITO layer (anode) formed on the glass substrate, and the hole injection layer is 60 nm thick. Then, N, N'-Bis (1-naphthalenyl) -N, N'-bis-phenyl- (1,1'-biphenyl) -4,4'-diamine (hereinafter abbreviated as NPB) Vacuum deposition to a thickness of 60 nm to form a hole transport layer.

Next, a light emitting layer having a thickness of 30 nm was formed on the hole transport layer, wherein compound 1-21 (first host), compound 2-43 (second host) and compound 3-90 (third host) were 5: 3: A mixture of the weight ratio of 2 was used as a host, and bis- (1-phenylisoquinolyl) iridium (III) (abbreviated as (piq) ₂ Ir (acac)) was used as a dopant, but the host and dopant were 95: 5 weight ratio was used.

Next, (1,1'-bisphenyl) -4-oleito) bis (2-methyl-8-quinolinoleito) aluminum (hereinafter abbreviated as BAlq) was vacuum-deposited on the light emitting layer to a thickness of 10 nm. A hole blocking layer was formed, and Bis (10-hydroxybenzo [h] quinolinato) beryllium (hereinafter abbreviated as BeBq ₂ ) was deposited to a thickness of 50 nm to form an electron transport layer. Thereafter, LiF was deposited to a thickness of 0.2 nm on the electron transport layer to form an electron injection layer, and then an Al was deposited to a thickness of 150 nm to form a cathode, thereby manufacturing an organic electroluminescent device.

[Example 2] to [Example 12]

An organic electroluminescent device was manufactured in the same manner as in Example 1, except that a mixture of compounds shown in Table 10 was used as a host material for the light emitting layer.

[Comparative Example 1] and [Comparative Example 2]

An organic electroluminescent device was manufactured in the same manner as in Example 1, except that Compound 1-101 was used alone (Comparative Example 1) or ref 4 compound was used alone (Comparative Example 2) as the host material of the emission layer. Produced.

Comparative Example 3

An organic electroluminescent device was manufactured in the same manner as in Example 1, except for using a mixture of Compound 1-101 and ref 4 as a host material of the emission layer.

[Comparative Example 4]

An organic electroluminescent device was manufactured in the same manner as in Example 1, except that the following ref 1 compound, ref 3 compound and compound 2-34 were used as a host material of the light emitting layer.

[Comparative Example 5]

An organic light emitting diode was manufactured according to the same method as Example 1 except for using a mixture of ref 3 compound, compound 2-34, and compound 3-99 as a host material of the emission layer.

Comparative Example 6

An organic light emitting diode was manufactured according to the same method as Example 1 except for using a mixture of ref 5 compound, compound 2-34 and compound 3-99 as a host material of the emission layer.

The electroluminescence (EL) characteristics of the organic electroluminescent devices prepared according to Examples 1 to 12 and Comparative Examples 1 to 6 were measured by applying a forward bias DC voltage to PR-650 of photoresearch. The T95 lifetime was measured using McScience's life measurement equipment at 2500 cd / m ² standard brightness. The measurement results are shown in Table 10 below.

<ref 1> <ref 2> <ref 3> <ref 4> <ref 5>

TABLE 10

From the results of Table 10, as in Examples 1 to 12 of the present invention, when a compound represented by the formula (1), (2) and (3) is used as a phosphorescent host, the device using a single material (Comparative Example 1 , Comparative Example 2), a device used by mixing only two compounds (Comparative Example 3), a device using a mixture of Comparative Compounds (refs. 1-4) (Comparative Example 4), and each compound belonging to It can be seen that the driving voltage, efficiency and lifespan are remarkably improved compared to the devices (Comparative Example 5, Comparative Example 6) used by mixing the comparative compounds.

In detail, Comparative Examples 3 to 6, in which two or more compounds were mixed and used as a host rather than Comparative Example 1 and Comparative Example 2 using the compound of the present invention represented by Formula 1 and Comparative Compound ref 4 as a single host, respectively In the case of the device characteristics are improved. In addition, compared to the case where two kinds of the compound of the present invention and one of the comparative compounds were used (Comparative Example 5, Comparative Example 6), the compounds belonging to the formulas (1), (2) and (3) of the present invention were mixed and used as a host. It can be seen that the devices of Examples 1 to 12 of the present invention significantly improve the efficiency and lifespan and lower the driving voltage.

The inventors of the present invention determine that each of the substances of Formula 1, Formula 2, and Formula 3, and mixtures thereof, have novel properties other than those of the substances on the basis of the above experimental results, The PL lifetime for these compounds was measured. As a result, in the case of the mixture of the present invention Formula 1, Formula 2, and Formula 3, it was confirmed that a new PL wavelength was formed, unlike when it was a single compound. It was confirmed that the decrease and disappearance time of each single substance represented by Formula 3 increased from about 60 times to as much as about 360 times.

This means that not only electrons and holes move through the energy levels of each material when the compounds of the present invention are mixed, but also electrons, hole movements or energy due to exciplexes having new energy levels formed by mixing. It is believed that this is because the transmission path increases efficiency and lifespan. This, in turn, is an important example of the mixed thin film showing exciplex energy transfer and luminescence processes when using the inventive mixture.

In addition, the reason why the compound combinations such as the present invention is excellent is that due to the polycyclic compound represented by Formula 1 or more, it is possible to improve not only electrons but also stability for holes, T1, etc. When the compound represented by the formula (3) having a suitable energy band and high T1 is mixed, electron injection and transport ability is improved and stability is increased at the interface between the light emitting layer and the electron transport layer, and more holes move quickly and easily in the light emitting layer. Because it is. As a result, the charge balance in the light emitting layer of holes and electrons is increased, so that light emission is well achieved in the light emitting layer instead of the hole transport layer interface, and thus deterioration of the HTL interface is also reduced, thereby maximizing driving voltage, efficiency and lifetime of the device. will be.

Therefore, the combination of the compounds represented by the formulas (1), (2) and (3), respectively, is electrochemically synergistic to improve the performance of the entire device.

The above description is merely illustrative of the present invention, and those skilled in the art will appreciate that various modifications may be made without departing from the essential features of the present invention. Accordingly, the embodiments disclosed herein are not intended to limit the present invention but to describe the present invention, and the spirit and scope of the present invention are not limited by these embodiments. The scope of protection of the present invention should be interpreted by the following claims, and all descriptions within the scope equivalent thereto should be construed as being included in the scope of the present invention.

100: organic electric element 110: substrate
120: first electrode 130: hole injection layer
140: hole transport layer 141: buffer layer
150: light emitting layer 151: light emitting auxiliary layer
160: electron transport layer 170: electron injection layer
180: second electrode

Claims (17)

In an organic electric device comprising a first electrode, a second electrode and an organic material layer formed between the first electrode and the second electrode,
The organic material layer includes a phosphorescent light emitting layer, and the host of the phosphorescent light emitting layer includes a first compound represented by the following Chemical Formula 1, a second compound represented by the following Chemical Formula 2, and a third compound represented by the following Chemical Formula 3. An organic electric element characterized by:
<Formula 1><Formula2>

<Formula 3>

In the above formula,
Ring A and ring B are independently of each other an aromatic ring of C ₆ ~ C ₂₀ or hetero ring of C ₂ ~ C ₂₀ , provided that when one of ring A and ring B is a monocyclic ring, the other ring is a polycyclic ring or adjacent R ¹ They combine with each other to form a ring,
X ¹ and X ² are each independently a single bond, N- (L-Ar), O, S or C (R ') (R "), and m are each an integer of 0 or 1, and l + m is Is an integer of 1 or more,
X ⁴ to X ⁸ are independently of each other C (R ^c ) or N,
X ₄ to X ₆ are each independently C- (L-Ar ') or N, at least one of X ⁴ to X ⁶ is N,
Ar ¹ is independently of each other C ₆ ~ C ₆₀ An aryl group; Fluorenyl groups; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; Aliphatic ring group of C ₃ ~ C ₆₀ ; A fused ring group of an aliphatic ring of C ₃ ~ C ₆₀ and an aromatic ring of C ₆ ~ C ₆₀ ; And -L'-N (R _a ) (R _b );
Ar ⁶ to Ar ⁸ independently of each other C ₆ ~ C ₆₀ An aryl group; Fluorenyl groups; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; Aliphatic ring group of C ₃ ~ C ₆₀ ; And C ₃ ~ fused ring group of an aromatic ring of C ₆₀ of aliphatic rings and C ₆ ~ C _60; And combinations thereof.
L ¹ , and L ⁴ to L ⁶ are each independently a single bond; C ₆ ~ C ₆₀ arylene group; Fluorenylene groups; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; Aliphatic ring group of C ₃ ~ C ₆₀ ; And C ₃ ~ fused ring group of an aromatic ring of C ₆₀ of aliphatic rings and C ₆ ~ C _60; And combinations thereof.
R ¹ , R ³⁰ , R ³¹ , R 'and R "are independently of each other hydrogen; deuterium; halogen; cyano group; C ₆ ~ C ₆₀ aryl group; fluorenyl group; O, N, S, Si and P C ₂ ~ C ₆₀ Heterocyclic group containing at least one heteroatom, C ₃ ~ C ₆₀ Aliphatic ring group, C ₃ ~ C ₆₀ Aliphatic ring and C ₆ ~ C ₆₀ Aromatic ring fused ring group; C ₁ ~ C ₅₀ Alkyl group; C ₂ ~ C ₂₀ Alkenyl group; C ₂ ~ C ₂₀ Alkynyl group; C ₁ ~ C ₃₀ Alkoxy group; C ₆ ~ C ₂₀ Aryloxy group; -L'-N (R _a ) (R _b ); and combinations thereof, and adjacent groups may combine with each other to form a ring, and R ′ and R ″ may combine with each other to form a ring, a is an integer of 0 to 2, p and q are each an integer of 0 to 4, and when each of them is an integer of 2 or more, each of R ¹ , each R ³⁰ , and each R ³¹ are the same as or different from each other,
The A ring may be substituted with one or more R ² , the B ring may be substituted with one or more R ³ , R ² and R ³ are independently of each other hydrogen; heavy hydrogen; halogen; Cyano group; C ₆ ~ C ₆₀ aryl group; Fluorenyl groups; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; Aliphatic ring group of C ₃ ~ C ₆₀ ; A fused ring group of an aliphatic ring of C ₃ ~ C ₆₀ and an aromatic ring of C ₆ ~ C ₆₀ ; C ₁ ~ C ₅₀ Alkyl group; C ₂ ~ C ₂₀ Alkenyl group; Alkynyl groups of C ₂ to C ₂₀ ; C ₁ ~ C ₃₀ Alkoxy group; C ₆ -C ₃₀ aryloxy group; And -L'-N (R _a ) (R _b ); each of the plurality of R ^{2 and} each of the plurality of R ³ may be the same as or different from each other,
Ar is C ₆ ~ C ₆₀ An aryl group; Fluorenyl groups; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; Aliphatic ring group of C ₃ ~ C ₆₀ ; A fused ring group of an aliphatic ring of C ₃ ~ C ₆₀ and an aromatic ring of C ₆ ~ C ₆₀ ; And -L'-N (R _a ) (R _b );
Ar 'is hydrogen; heavy hydrogen; halogen; A silane group unsubstituted or substituted with a C ₁ -C ₂₀ alkyl group or a C ₆ -C ₂₀ aryl group; Cyano group; Nitro group; Import alkylthio of C ₁ -C _20; An alkoxy group of C ₁ -C ₂₀ ; C ₆ -C ₂₀ aryloxy group; An alkyl group of C ₁ -C ₂₀ ; Alkenyl groups of C ₂ -C ₂₀ ; An alkynyl group of C ₂ -C ₂₀ ; C ₆ ~ C ₆₀ aryl group; Fluorenyl groups; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; Aliphatic ring group of C ₃ ~ C ₆₀ ; A fused ring group of an aliphatic ring of C ₃ ~ C ₆₀ and an aromatic ring of C ₆ ~ C ₆₀ ; And -L'-N (R _a ) (R _b );
R ^c is hydrogen; heavy hydrogen; halogen; Cyano group; Nitro group; C ₆ -C ₂₀ aryl group; Fluorenyl groups; C ₂ ~ C ₂₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; Aliphatic ring group of C ₃ ~ C ₂₀ ; A fused ring group of an aliphatic ring of C ₃ ~ C ₂₀ and an aromatic ring of C ₆ ~ C ₂₀ ; C ₁ ~ C ₂₀ Alkyl group; C ₂ ~ C ₂₀ Alkenyl group; Alkynyl groups of C ₂ to C ₂₀ ; C ₁ ~ C ₂₀ Alkoxy group; C ₆ -C ₃₀ aryloxy group; And -L ^a -N (R ^a ) (R ^b ); It is selected from the group consisting of, adjacent R ^c may combine with each other to form a ring,
R ^a and R ^b are each independently a C ₆ ~ C ₂₀ aryl group; Fluorenyl groups; C ₂ ~ C ₂₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; Aliphatic ring group of C ₃ ~ C ₂₀ ; And it can be selected from the group consisting of a combination thereof,
L, L ', L ^a are each independently a single bond; C ₆ ~ C ₆₀ arylene group; Fluorenylene groups; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; Aliphatic ring group of C ₃ ~ C ₆₀ ; And C ₃ ~ C ₆₀ Aliphatic ring and C ₆ ~ C ₆₀ Aromatic ring fused ring group; It is selected from the group consisting of,
R _a and R _b are each independently hydrogen; C ₆ ~ C ₆₀ aryl group; Fluorenyl groups; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; Aliphatic ring group of C ₃ ~ C ₆₀ ; And a fused ring group of C ₃ to C ₆₀ aliphatic rings and C ₆ to C ₆₀ aromatic rings. The method of claim 1,
The ring A and ring B is an organic electric device, characterized in that independently selected from the group consisting of the formula a-1 to formula a-7:
<Formula a-1><Formulaa-2><Formulaa-3><Formulaa-4>

<Formula a-5><Formulaa-6><Formulaa-7>

In the above formula,
Z ¹ to Z ⁴⁸ are independently of each other C, C (R ^c ) or N, and R ^c is as defined in claim 1. The method of claim 1,
The L ¹ , L ^{4 To} L ^{6 It} is independently an organic electroluminescent device, characterized in that selected from the group consisting of the formula b-1 to b-13:
<Formula b-1><Formulab-2><Formulab-3><Formulab-4><Formulab-5><Formulab-6>

<Formula b-7><Formulab-8><Formulab-9><Formulab-10>

<Formula b-11><Formulab-12><Formulab-13>

In the above formula,
R ⁴ to R ⁶ are each independently hydrogen; heavy hydrogen; halogen; Cyano group; Nitro group; C ₆ -C ₂₀ aryl group; Fluorenyl groups; C ₂ ~ C ₂₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; Aliphatic ring group of C ₃ ~ C ₂₀ ; A fused ring group of an aliphatic ring of C ₃ ~ C ₂₀ and an aromatic ring of C ₆ ~ C ₂₀ ; C ₁ ~ C ₂₀ Alkyl group; C ₂ ~ C ₂₀ Alkenyl group; Alkynyl groups of C ₂ to C ₂₀ ; C ₁ ~ C ₂₀ Alkoxy group; C ₆ -C ₃₀ aryloxy group; And -L ^a -N (R ^a ) (R ^b ); It is selected from the group consisting of, adjacent groups can combine with each other to form a ring,
Y is independently of each other N- (L ^a -Ar ^a ), O, S or C (R ^d ) (R ^e ),
Z ⁴⁹ to Z ⁵¹ are independently of each other C, C (R ^c ) or N, and at least one of Z ⁴⁹ to Z ⁵¹ is N,
f, h, i and j are each an integer of 0 to 4, g is an integer of 0 to 6, k and l 'are each an integer of 0 to 3, m' is an integer of 0 to 2, n is Are an integer from 0 to 3, and when each of them is an integer of 2 or more, each of R ⁴ , each R ⁵ , and each R ⁶ is the same as or different from each other,
R ^c , R ^d and R ^e are each independently hydrogen; heavy hydrogen; halogen; Cyano group; Nitro group; C ₆ -C ₂₀ aryl group; Fluorenyl groups; C ₂ ~ C ₂₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; Aliphatic ring group of C ₃ ~ C ₂₀ ; A fused ring group of an aliphatic ring of C ₃ ~ C ₂₀ and an aromatic ring of C ₆ ~ C ₂₀ ; C ₁ ~ C ₂₀ Alkyl group; C ₂ ~ C ₂₀ Alkenyl group; Alkynyl groups of C ₂ to C ₂₀ ; C ₁ ~ C ₂₀ Alkoxy group; C ₆ -C ₃₀ aryloxy group; And -L ^a -N (R ^a ) (R ^b ); R ^d and R ^e may be bonded to each other or adjacent R ^c may be bonded to each other to form a ring.
Ar ^a is a C ₆ ~ C ₂₀ aryl group; Fluorenyl groups; C ₂ ~ C ₂₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; Aliphatic ring group of C ₃ ~ C ₂₀ ; And combinations thereof.
L ^a , R ^a and R ^b are as defined in claim 1. The method of claim 1,
Formula 1 is an organic electric device, characterized in that represented by the formula 1-A or 1-B:
<Formula 1-A><Formula1-B>

In the above formula, A ring, B ring, R ¹ , L ¹ , Ar ¹ , X ¹ , X ² and a are the same as defined in claim 1. The method of claim 1,
Formula 1 is an organic electric device, characterized in that represented by one of the following formula 1-1 to formula 1-44:
<Formula 1-1><Formula1-2><Formula1-3>

<Formula 1-4><Formula1-5><Formula1-6><Formula1-7>

<Formula 1-8><Formula1-9><Formula1-10><Formula1-11>

<Formula 1-12><Formula1-13><Formula1-14><Formula1-15>

<Formula 1-16><Formula1-17><Formula1-18><Formula1-19>

<Formula 1-20><Formula1-21><Formula1-22><Formula1-23>

<Formula 1-24><Formula1-25><Formula1-26>

<Formula 1-27><Formula1-28><Formula1-29><Formula1-30>

<Formula 1-31><Formula1-32><Formula1-33><Formula1-34>

<Formula 1-35><Formula1-36><Formula1-37><Formula1-38>

<Formula 1-39><Formula1-40><Formula1-41><Formula1-42>

In the above formula,
R ¹¹ is independently of each other hydrogen; heavy hydrogen; halogen; C ₆ -C ₂₀ aryl group; Fluorenyl groups; C ₂ ~ C ₂₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; Aliphatic ring group of C ₃ ~ C ₂₀ ; A fused ring group of an aliphatic ring of C ₃ ~ C ₂₀ and an aromatic ring of C ₆ ~ C ₂₀ ; C ₁ ~ C ₂₀ Alkyl group; C ₂ ~ C ₂₀ Alkenyl group; Alkynyl groups of C ₂ to C ₂₀ ; C ₁ ~ C ₂₀ Alkoxy group; C ₆ -C ₂₀ aryloxy group; And -L ^a -N (R ^a ) (R ^b ); It is selected from the group consisting of, adjacent groups can combine with each other to form a ring,
b, c and a 'are each an integer from 0 to 4, b' and c 'are each an integer from 0 to 6, b "and c" are each an integer from 0 to 8, and each of them is an integer of 2 or more. , Each R ¹ , each R ² , each R ³ , each R ¹¹ are the same as or different from each other,
X ¹ , X ² , Ar ¹ , L ¹ , R ¹ , R ² , R ³ L ^a , R ^a , R ^b and a are as defined in claim 1. The method of claim 1,
Formula 1 is an organic electric device, characterized in that represented by one of the formula 1-C to Formula 1-J:
<Formula 1-C><Formula1-D><Formula1-E><Formula1-F>

<Formula 1-G><Formula1-H><Formula1-I><Formula1-J>

In the above formula, A ring, B ring, R ¹ , L ¹ , Ar ¹ , L, Ar, R ', R "and a are as defined in claim 1. The method of claim 1,
Formula 2 is an organic electric device, characterized in that represented by the following formula 2-A or 2-B:
<Formula 2-A><Formula2-B>

In the above formula,
L ₄ is a single bond; C ₆ ~ C ₆₀ arylene group; Fluorenylene groups; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; Aliphatic ring group of C ₃ ~ C ₆₀ ; And C ₃ ~ C ₆₀ Aliphatic ring and C ₆ ~ C ₆₀ Aromatic ring fused ring group; It is selected from the group consisting of,
R ³² to R ³⁴ are each independently hydrogen; heavy hydrogen; halogen; Cyano group; Nitro group; C ₆ -C ₂₀ aryl group; Fluorenyl groups; C ₂ ~ C ₂₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; Aliphatic ring group of C ₃ ~ C ₂₀ ; A fused ring group of an aliphatic ring of C ₃ ~ C ₂₀ and an aromatic ring of C ₆ ~ C ₂₀ ; C ₁ ~ C ₂₀ Alkyl group; C ₂ ~ C ₂₀ Alkenyl group; Alkynyl groups of C ₂ to C ₂₀ ; C ₁ ~ C ₂₀ Alkoxy group; C ₆ -C ₃₀ aryloxy group; And -L ^a -N (R ^a ) (R ^b ); It is selected from the group consisting of, adjacent groups can combine with each other to form a ring,
r is an integer from 0 to 3, s is an integer from 0 to 5, t is an integer from 0 to 4, u is an integer from 0 to 4, each of R ³² , each of which is an integer of 2 or more, each R ³³ , each R ³⁴ are the same as or different from each other,
X ⁹ is N- (L ^a -Ar ^a ), O, S, C (R ^c ), C (R ^d ) (R ^e ) or N,
R ^d and R ^e are each independently hydrogen; heavy hydrogen; halogen; Cyano group; Nitro group; C ₆ -C ₂₀ aryl group; Fluorenyl groups; C ₂ ~ C ₂₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; Aliphatic ring group of C ₃ ~ C ₂₀ ; A fused ring group of an aliphatic ring of C ₃ ~ C ₂₀ and an aromatic ring of C ₆ ~ C ₂₀ ; C ₁ ~ C ₂₀ Alkyl group; C ₂ ~ C ₂₀ Alkenyl group; Alkynyl groups of C ₂ to C ₂₀ ; C ₁ ~ C ₂₀ Alkoxy group; C ₆ -C ₃₀ aryloxy group; And -L ^a -N (R ^a ) (R ^b ); and R ^d and R ^e may be bonded to each other to form a ring.
Ar ^a is a C ₆ ~ C ₂₀ aryl group; Fluorenyl groups; C ₂ ~ C ₂₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; Aliphatic ring group of C ₃ ~ C ₂₀ ; And combinations thereof.
R ³⁰ , R ³¹ , X ⁴ to X ⁸ , R ^c , L ^a , R ^a , R ^b and p are as defined in claim 1. The method of claim 1,
Formula 2 is an organic electric device, characterized in that represented by one of the formula 2-C to Formula 2-F:
<Formula 2-C><Formula2-D><Formula2-E><Formula2-F>

In the above formula, p 'is an integer from 0 to 6, p "is an integer from 0 to 8, and when each of them is an integer of 2 or more, each R ³⁰ , each R ³¹ is the same as or different from each other, X ⁴ To X ⁸ , R ³⁰ , R ³¹ and q are as defined in claim 1. The method of claim 1,
Formula 2 is an organic electric device, characterized in that represented by the formula 2-G:
<Formula 2-G>

In the above formula, v and w are each an integer of 0 to 2, v + w is an integer of 1 or more, and X ⁴ to X ⁸ are as defined in claim 1. The method of claim 1,
Formula 3 is an organic electric device, characterized in that represented by one of the formula 3-A to 3-C:
<Formula 3-A><Formula3-B><Formula3-C>

In the above formula, L ⁴ to L ⁶ , Ar ⁶ to Ar ⁸ are the same as defined in claim 1. The method of claim 1,
Formula 3 is an organic electric device, characterized in that represented by one of the formula 3-1 to 3-8:
<Formula 3-1><Formula3-2>

<Formula 3-3><Formula3-4>

<Formula 3-5><Formula3-6>

<Formula 3-7><Formula3-8>

In the above formula,
X ₇ and X ₈ are independently of each other a single bond, N- (L ^a -Ar ^a ), O, S or C (R ^d ) (R ^e ), at least one of them is not a single bond,
Y ¹ to Y ³⁸ are independently of each other C, C (R _c ) or N,
R _c , R ^d and R ^e are each independently hydrogen; heavy hydrogen; halogen; Cyano group; Nitro group; C ₆ -C ₂₀ aryl group; Fluorenyl groups; C ₂ ~ C ₂₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; Aliphatic ring group of C ₃ ~ C ₂₀ ; A fused ring group of an aliphatic ring of C ₃ ~ C ₂₀ and an aromatic ring of C ₆ ~ C ₂₀ ; C ₁ ~ C ₂₀ Alkyl group; C ₂ ~ C ₂₀ Alkenyl group; Alkynyl groups of C ₂ to C ₂₀ ; C ₁ ~ C ₂₀ Alkoxy group; C ₆ -C ₂₀ aryloxy group; And -L ^a -N (R ^a ) (R ^b ); R ^d and R ^e may be bonded to each other or adjacent R _c may be bonded to each other to form a ring.
R ¹³ is independently of each other hydrogen; heavy hydrogen; halogen; A silane group unsubstituted or substituted with a C ₁ -C ₂₀ alkyl group or a C ₆ -C ₂₀ aryl group; Siloxane groups; Boron group; Germanium group; Cyano group; Nitro group; Import alkylthio of C ₁ -C _20; An alkoxy group of C ₁ -C ₂₀ ; C ₆ -C ₂₀ aryloxy group; An alkyl group of C ₁ -C ₂₀ ; Alkenyl groups of C ₂ -C ₂₀ ; An alkynyl group of C ₂ -C ₂₀ ; C ₆ -C ₂₀ aryl group; C ₆ -C ₂₀ aryl group substituted with deuterium; Fluorenyl groups; C ₂ -C ₂₀ heterocyclic group including at least one heteroatom selected from the group consisting of O, N, S, Si and P; Aliphatic ring groups of C ₃ -C ₂₀ ; C ₇ -C ₂₀ arylalkyl group; Arylalkenyl group of C ₈ -C ₂₀ ; -L ^a -N (R ^a ) (R ^b ); And it may be selected from the group consisting of a combination thereof, adjacent groups may combine with each other to form a ring,
e 'is an integer of 0-4, f' = an integer of 0-2, g 'is an integer of 0-9, h' is an integer of 0-5, and when each of these is an integer of 2 or more, a plurality of R ¹³ are each Are the same as or different from each other,
Ar ^a is a C ₆ ~ C ₂₀ aryl group; Fluorenyl groups; C ₂ ~ C ₂₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; Aliphatic ring group of C ₃ ~ C ₂₀ ; And combinations thereof.
X ₄ to X ₆ , L ⁴ to L ⁶ , Ar ⁷ , Ar ⁸ , L ^a , R ^a and R ^b are as defined in claim 1. The method of claim 1,
Compound represented by the formula (1) is an organic electric device, characterized in that one of the following compounds:

. The method of claim 1,
Compound represented by the formula (2) is an organic electric device, characterized in that one of the following compounds:

. The method of claim 1,
Compound represented by the formula (3) is an organic electric device, characterized in that one of the following compounds:

. The method of claim 1,
The first compound is 40 to 80% by weight, the second compound is 10 to 30% by weight, the third compound is an organic electric device, characterized in that 10 to 40% by weight. A display device comprising the organic electroluminescent element of claim 1; And
And a controller for driving the display device. The method of claim 16,
The organic electroluminescent device is selected from the group consisting of an organic electroluminescent device, an organic solar cell, an organic photoconductor, an organic transistor, a monochromatic lighting device and a quantum dot display device.

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