WO2018034443A1

WO2018034443A1 - Compound for organic electric element, organic electric element using same, and electronic device thereof

Info

Publication number: WO2018034443A1
Application number: PCT/KR2017/008088
Authority: WO
Inventors: 장재완; 김원삼; 박보람; 최승원; 하종진; 박정환; 이선희; 이문재
Original assignee: 덕산네오룩스 주식회사
Priority date: 2016-08-17
Filing date: 2017-07-27
Publication date: 2018-02-22
Also published as: KR20180019879A; KR102574912B1

Abstract

Disclosed are a compound represented by chemical formula 1, an organic electric element including a first electrode, a second electrode, and an organic layer disposed between the first and the second electrode, and an electronic device comprising the same organic electric element. Including the compound represented by chemical formula 1 in an organic layer thereof, an organic electric element can be reduced in operating voltage and improved in light emission efficiency and life span.

Description

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

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

In general, organic light emitting phenomenon refers to a phenomenon of converting electrical energy into light energy using an organic material. An organic electric element 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 electric 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.

The material used as the organic material layer in the organic electric element may be classified into a light emitting material and a charge transport material such as a hole injection material, a hole transport material, an electron transport material, an electron injection material and the like according to a function.

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 material may be classified into blue, green, and red light emitting materials and yellow and orange light emitting materials required to achieve a better natural color according to the light emitting color.

On the other hand, when only one material is used as the light emitting material, the maximum emission wavelength is shifted to a long wavelength due to the intermolecular interaction, and the color purity decreases or the efficiency of the device decreases due to the 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 is required for 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 the problem of efficiency and lifespan must also be solved.

Efficiency, lifespan, and driving voltage are related to each other, and as the efficiency increases, the driving voltage is relatively decreased, and as the result, 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 life. However, simply improving the organic material layer does not maximize the efficiency. This is because a long lifetime and high efficiency can be simultaneously achieved when an optimal combination of energy level and T ₁ value between each organic material layer, intrinsic properties (mobility, interfacial properties, etc.) of the material is achieved. Therefore, there is a need for development of a light emitting material having high thermal stability and efficiently achieving a charge balance in the light emitting layer.

That is, in order to fully exhibit the excellent characteristics of the organic electric device, a material forming the organic material layer in the device, such as a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, etc., is supported by a stable and efficient material. It should be preceded, but the development of a stable and efficient organic material layer for an organic electric device has not been made enough. Therefore, the development of new materials is continuously required, and in particular, the development of the host material of the light emitting layer is urgently required.

An object of the present invention is to provide a compound capable of lowering the driving voltage of the device and improving the luminous efficiency, color purity and lifetime of the device, an organic electric device using the same, and an electronic device thereof.

In one aspect, the present invention provides a compound represented by the following formula (1).

In another aspect, the present invention provides an organic electronic device using the compound represented by the above formula and an electronic device thereof.

By using the compound according to the embodiment of the present invention, not only can the driving voltage of the device be lowered, but the luminous efficiency, color purity, and lifetime of the device can be greatly improved.

[Description of the code]

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

In describing the components of the present invention, terms such as first, second, A, B, (a), and (b) can be used. These terms are only for distinguishing the components from other components, and the nature, order or order of the components are not limited by the terms. If a component is described as being "connected", "coupled" or "connected" to another component, that component may be directly connected to or connected to that other component, but there may be another configuration between each component. It is to be understood that the elements may be "connected", "coupled" or "connected".

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 "on top of" but also another component in between. It is to be understood that this may also include cases. On the contrary, when 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.

As used in this specification and the appended claims, unless otherwise indicated, the meanings of the following terms are as follows.

The term "halo" or "halogen" as used herein is fluorine (F), bromine (Br), chlorine (Cl) or iodine (I) unless otherwise indicated.

As used herein, the term "alkyl" or "alkyl group" has a single bond of 1 to 60 carbon atoms, unless otherwise indicated, and is a straight chain alkyl group, branched chain alkyl group, cycloalkyl (alicyclic) group, alkyl-substituted cyclo Radicals of saturated aliphatic functional groups, including alkyl groups, cycloalkyl-substituted alkyl groups.

As used herein, the term "haloalkyl group" or "halogenalkyl group" means an alkyl group substituted with halogen unless otherwise specified.

As used herein, the term "alkenyl group" or "alkynyl group", unless stated otherwise, has a double or triple bond of 2 to 60 carbon atoms, and includes a straight or branched chain group, and is not limited thereto. It is not.

The term "cycloalkyl" as used herein, unless otherwise stated, refers to alkyl forming a ring having 3 to 60 carbon atoms, without being limited thereto.

As used herein, the term "alkoxyl group", "alkoxy group", or "alkyloxy group" means an alkyl group to which an oxygen radical is attached, and unless otherwise specified, has a carbon number of 1 to 60, and is limited herein. It is not.

As used herein, the term "aryloxyl group" or "aryloxy group" means an aryl group to which an oxygen radical is attached, and unless otherwise specified, has a carbon number of 6 to 60, but is not limited thereto.

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 terms "aryl group" and "arylene group" have a carbon number of 6 to 60 unless otherwise stated, but 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.

"Heterocyclic groups" may also include rings comprising SO ₂ in place of the carbon forming the ring. For example, a "heterocyclic group" includes the following compounds.

As used herein, the term “ring” includes monocyclic and polycyclic rings, includes hydrocarbon rings as well as heterocycles including at least one heteroatom, and includes aromatic and nonaromatic rings.

As used herein, the term "polycyclic" includes ring assemblies, fused multiple ring systems and spiro compounds, such as biphenyl, terphenyl, and the like, including aromatics as well as nonaromatics, hydrocarbons The ring as well includes heterocycles comprising at least one heteroatom.

As used herein, the term "ring assemblies" means that two or more ring systems (single or conjugated ring systems) are directly connected to each other through a single bond or a double bond and directly between such rings. It means that the number of linkages is one less than the total number of ring systems in this compound. Ring aggregates may have the same or different ring systems directly connected to each other via a single bond or a double bond.

As used herein, the term "conjugated multiple ring systems" refers to a covalently fused ring form of at least two atoms, including a ring system in which two or more hydrocarbons are fused together and at least one heteroatom. And heterocyclic systems having at least one conjugated form. These conjugated several ring systems can be aromatic rings, heteroaromatic rings, aliphatic rings or combinations of these rings.

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

Also, when prefixes are named consecutively, it means that the substituents are listed in the order described first. For example, an arylalkoxy group means an alkoxy group substituted with an aryl group, an alkoxycarbonyl group means a carbonyl group substituted with an alkoxy group, and in the case of an arylcarbonylalkenyl group, an alkenyl group substituted with an arylcarbonyl group is used herein. The arylcarbonyl group is a carbonyl group substituted with an aryl group.

Also, unless expressly stated, the term "substituted" in the term "substituted or unsubstituted" refers to deuterium, halogen, amino groups, nitrile groups, nitro groups, C ₁ -C ₂₀ alkyl groups, C ₁ -C ₂₀ alkoxy group, C ₁ -C ₂₀ alkylamine group, C ₁ -C ₂₀ alkylthiophene group, C ₆ -C ₂₀ arylthiophene group, C ₂ -C ₂₀ alkenyl group, C ₂ -C ₂₀ alkynyl, C ₃ -C ₂₀ cycloalkyl group, C ₆ -C ₂₀ aryl group, of a C ₆ -C ₂₀ aryl group substituted with a heavy hydrogen, C ₈ -C ₂₀ aryl alkenyl group, a silane group, a boron Substituted by at least one substituent selected from the group consisting of a group, a germanium group, and a C ₂ -C ₂₀ heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P It is not limited to these substituents.

The group name corresponding to the aryl group, arylene group, heterocyclic group, etc. exemplified in each symbol and examples of the substituents in this specification may describe 'the name of the group reflecting the singer', but is described as 'the parent compound name'. You may. For example, in the case of phenanthrene, which is a kind of aryl group, the monovalent group is phenanthryl and the divalent group may be grouped with a singer, such as phenanthryl, to describe the group name. 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 Are each bonded as follows, where R ¹ may be the same or different from each other, and when a is an integer from 4 to 6, it is bonded to the carbon of the benzene ring in a similar manner, while the indication of hydrogen bonded to the carbon forming the benzene ring Is omitted.

Hereinafter, exemplary embodiments of the present invention will be described in detail with reference to the accompanying drawings.

In adding reference numerals to the components of each drawing, it should be noted that the same reference numerals are assigned to the same components as much as possible even though they are shown in different drawings. In addition, 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.

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 provided between the two 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, and an electron injection layer 170 on the first electrode 120 in sequence. 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 electric element according to an embodiment of the present invention is a protective layer formed on one surface of the both sides of the first electrode opposite to the organic material layer and / or one surface of the both sides of the second electrode opposite to the organic material layer or A light efficiency improvement layer may further include a capping layer.

Compound according to an embodiment of the present invention applied to the organic layer is a hole injection layer 130, a hole transport layer 140, a light emitting auxiliary layer 151, an electron transport auxiliary layer, an electron transport layer 160, an electron injection layer ( 170, a host or dopant material of the light emitting layer 150, or a material of the light efficiency improving layer. For example, the compound of the present invention may be used as the light emitting layer 150, the hole transport layer 140 and / or the light emitting auxiliary layer 151 material, preferably may be used as the light emitting layer 150 material.

Meanwhile, even in the same core, band gaps, electrical characteristics, and interface characteristics may vary depending on which substituents are bonded at which positions. Therefore, the selection of the cores and the combination of sub-substituents bonded thereto may be performed. In particular, long life and high efficiency can be simultaneously achieved when an optimal combination of energy level and T ₁ value and intrinsic properties (mobility, interfacial properties, etc.) between organic layers is achieved.

Therefore, in the present invention, by forming the light emitting layer 150 using the compound represented by the formula (1) by optimizing the energy level and T ₁ value between each organic material layer, the intrinsic properties (mobility, interfacial characteristics, etc.) of the organic organic device Can improve the service life and efficiency at the same time.

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 a hole transport layer 140, a light emitting layer 150, an electron transport layer 160 and an 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 material layer is a solution or solvent process (e.g., spin coating process, nozzle printing process, inkjet printing process, slot coating process, dip coating process, roll-to-roll process, doctor blading) using various polymer materials. 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 may 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 the material used.

WOLED (White Organic Light Emitting Device) has the advantage that can be manufactured using the color filter technology of the existing LCD while being easy to realize high resolution and excellent processability. Various structures for white organic light emitting devices mainly used as backlight devices have been proposed and patented. Representatively, a side-by-side method in which R (Red), G (Green), and B (Blue) light emitting parts are mutually planarized, and a stacking method in which R, G, and B light emitting layers are stacked up and down. And a color conversion material (CCM) method using photo-luminescence of an inorganic phosphor by using electroluminescence by a blue (B) organic light emitting layer and light therefrom. May also be applied to these WOLEDs.

In addition, the organic electroluminescent device according to an embodiment of the present invention may be one of an organic electroluminescent device, an organic solar cell, an organic photosensitive member, an organic transistor, a monochromatic or white illumination 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, the compound which concerns on one aspect of this invention is demonstrated.

Compound according to an aspect of the present invention is represented by the following formula (1).

In Formula 1, each symbol is defined as follows.

Ring A is one of the following Chemical Formulas 1-1 to 1-3.

R ¹ -R ⁹ of Formula 1 and R ¹⁰ -R ¹⁷ of Formulas 1-1 to 1-3 are each independently hydrogen; heavy hydrogen; halogen; C ₆ ~ C ₆₀ Aryl group; Fluorenyl group; C ₂ -C ₆₀ heterocyclic group containing at least one hetero atom of O, N, S, Si and P; A fused ring group of an aromatic ring of C ₆ ~ C ₆₀ and an aliphatic ring 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 alkoxyl group; C ₆ -C ₃₀ aryloxy group; And -L'-N (R _a ) (R _b ); It is selected from the group consisting of. In addition, R ¹ -R ¹⁷ may be bonded to each other adjacent groups to form a ring, wherein the ring formed is an aromatic ring of C ₆ -C ₆₀ ; Fluorene; C ₂ -C ₆₀ heterocycle comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P; Or a fused ring group of an aromatic ring of C ₆ -C ₆₀ and an aliphatic ring of C ₃ -C ₆₀ .

When R ¹ -R ¹⁷ is aryl, preferably an aryl group of C ₆ to C ₃₀ , more preferably an aryl group of C ₆ to C ₁₈ , and exemplarily phenyl, biphenyl, terphenyl, naphthyl, Phenanthrene, pyrene and the like. When R ¹ -R ¹⁷ is a heterocyclic group, it is preferably a heterocyclic group of C ₂ ~ C ₃₀ , more preferably a heterocyclic group of C ₂ ~ C ₁₂ , for example pyridyl, quinazoline, triazine , Benzoquinazolin, pyrimidine, benzothiophenpyrimidine and the like.

X is N (-L ¹ -Ar ¹ ), O, S or C (R ') (R ").

In N (-L ¹ -Ar ¹ ), L ¹ 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; And a fused ring group of a C ₃ ~ C ₆₀ aliphatic ring and a C ₆ ~ C ₆₀ aromatic ring; Ar ¹ is an C ₆ ~ C ₆₀ aryl group; Fluorenyl group; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; Fused ring group of an aromatic ring of C ₃ ~ C ₆₀ of aliphatic rings and C ₆ ~ C _60; And -L'-N (R _a ) (R _b ); It is selected from the group consisting of.

When Ar ¹ is an aryl group, preferably an C ₆ -C ₃₀ aryl group, more preferably a C ₆ -C ₁₈ aryl group, for example phenyl, biphenyl, terphenyl, naphthyl, phenanthrene, pi Lene, triphenylene and the like. When Ar ¹ is a heterocyclic group, it is preferably a heterocyclic group of C ₂ ~ C ₃₀ , more preferably a heterocyclic group of C ₂ ~ C ₁₃ , illustratively pyridyl, pyrimidine, triazine, quinazoline , Benzoquinazolin, benzothiophenpyrimidine, phenanthridine, carbazole, benzopuropyrimidine and the like.

In C (R ′) (R ″), R ′ and R ″ are each independently of the alkyl group of C ₁ to C ₅₀ ; C ₆ ~ C ₆₀ Aryl group; Fluorenyl group; C ₂ -C ₆₀ heterocyclic group containing at least one hetero atom of O, N, S, Si and P; And it is selected from the group consisting of a fused ring of C ₆ ~ C ₆₀ aromatic ring and C ₃ ~ C ₆₀ Aliphatic ring, R 'and R "may be bonded to each other to form a ring.

In -L'-N (R _a ) (R _b ), L '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; And a fused ring group of C ₃ to C ₆₀ aliphatic ring and C ₆ to C ₆₀ aromatic ring; R _a and R _b are each independently of the C ₆ to C ₆₀ aryl group; Fluorenyl group; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; And a fused ring group of C ₃ to C ₆₀ aliphatic ring and C ₆ to C ₆₀ aromatic ring; R _a and R _b may be bonded to each other to form a ring.

When L ¹ and L 'are an aryl group, it is preferably an arylene group of C ₆ ~ C ₃₀ , more preferably an arylene group of C ₆ ~ C ₁₂ , may be phenyl, biphenyl, naphthalene and the like. When L ¹ and L 'are heterocyclic groups, preferably a C ₂ ~ C ₃₀ heterocyclic group, more preferably a C ₂ ~ C ₁₃ heterocyclic group, for example pyridine, pyrimidine, triazine, Quinazoline, benzoquinazolin, benzothiophenpyrimidine, phenanthridine, carbazole, benzofuropyrimidine and the like.

When R ′, R ″, R _a and R _b are aryl groups, preferably an aryl group of C ₆ to C ₃₀ , more preferably an aryl group of C ₆ to C ₁₈ , for example phenyl, biphenyl, ter Phenyl, naphthyl and the like, when R ', R "is an alkyl group, preferably may be an alkyl group of C ₁ ~ C ₁₀ and may be a methyl group, and when R _a and R _b is a fluorenyl group 9,9-dimethyl-9 H -fluorene.

R ¹ to R ¹⁷ , Ar ¹ , R ′, R ″, R _a , R _b , L ′ and L ¹ are an aryl group, fluorenyl group, heterocyclic group, fused ring group, alkyl group, alkenyl group, alkynyl group , An alkoxyl group, an aryloxy group, an arylene group or a fluorenylene group, each of which is deuterium; halogen; a silane group unsubstituted or substituted with an alkyl group of C ₁ -C ₂₀ or an aryl group of C ₆ -C ₂₀ ; ; boron group; germanium group; cyano group; nitro group; C ₁ -C ₂₀ alkylthio Sy of; an alkoxy group of _{_{_{C 1 -C 20; C 1 -C}}} 20 alkyl group; an alkenyl group of C ₂ -C _20; C alkynyl of ₂ -C _20; an aryl group of C ₆ -C ₂₀ substituted with heavy hydrogen;; an aryl group of C ₆ -C ₂₀ fluorenyl group; O, N, S, at least one selected from the group consisting of Si and P C ₂ -C ₂₀ heterocyclic group containing a hetero atom of; C ₃ -C ₂₀ cycloalkyl group; C ₇ -C ₂₀ arylalkyl group; and C ₈ -C ₂₀ arylalkenyl group selected from the group consisting of More than one substitution May be further substituted with a group.

Formula 1 may be represented by any one of the following Formula 2 to Formula 7.

In Chemical Formulas 1 to 7, R ¹ to R ¹⁷ and X are the same as defined in Chemical Formula 1.

Preferably, Chemical Formula 1 may be represented by any one of the following Chemical Formulas 8-1 to 11-6. In Formulas 8-1 to 8-6, X is N (-L ¹ -Ar ¹ ), and in Formulas 9-1 to 10-6, X is C (R ′) (R ″), and in Formulas 10-1 to 10- 6 is the case where X is O, and Formulas 11-1 to 11-6 are X is S.

In Chemical Formulas 8-1 to 11-6, R ¹ to R ¹⁷ are the same as defined in Chemical Formula 1.

Specifically, Formula 1 is one of the following compounds.

In another embodiment, the present invention comprises a first electrode; Second electrode; And an organic material layer disposed between the first electrode and the second electrode and containing the compound represented by Chemical Formula 1 or formed by Chemical Formula 1. In this case, the compound represented by Formula 1 may be included in at least one layer of a hole injection layer, a hole transport layer, a light emitting auxiliary layer, a light emitting layer, an electron transport auxiliary layer, an electron transport layer and an electron injection layer of the organic material layer, or a single compound or It may be contained as a component of two or more mixtures. That is, the compound represented by Formula 1 may be used as a material of a hole injection layer, a hole transport layer, a light emitting auxiliary layer, a light emitting layer, an electron transport auxiliary layer, an electron transport layer or an electron injection layer. Preferably, the compound represented by Formula 1 may be used as a phosphorescent host material of the light emitting layer, more preferably, a red phosphorescent host material.

In still another embodiment of the present invention, the present invention provides a light efficiency improving layer formed on at least one side of the one side of the first electrode opposite to the organic material layer or one side of the second electrode opposite to the organic material layer. It provides an organic electric element further comprising.

Hereinafter, the synthesis examples of the compound represented by the formula (1) according to the present invention and the production examples of the organic electric device will be described in detail by way of examples, but the present invention is not limited to the following examples.

합성예Synthesis Example

By way of example, the compounds according to the present invention may be synthesized by the following Schemes 1 and 2, but is not limited thereto.

Where X is N (-L'-Ar ¹ ) and X = Br, I or Cl

Where X is S, O or CR'R ”

I. Core의 합성I. Synthesis of Core

1. Core 1의 1.Core 1 합성예Synthesis Example

Synthesis of Core 1-a

2,6-Dibromonaphthalene (30 g, 104.91 mmol) to (2-nitrophenyl) boronic acid (17.51 g, 104.91 mmol), Pd (PPh ₃ ) ₄ (3.64 g, 3.15 mmol), K ₂ CO ₃ (43.50 g, 314.72 mmol), THF (300 ml), H ₂ O (150 ml) were added and refluxed at 90 ° C. for 12 hours. At the end of the reaction, the reaction was cooled to room temperature, extracted with MC, and washed with water. The organic layer was dried over MgSO ₄ , concentrated, and the resulting organic was separated using a silicagel column to give 17.9 g (52%) of product.

Synthesis of Core 1-b

Add triphenylphosphine (35.77 g, 136.36 mmol) and o-dichlorobenzene (o-DCB) (150 ml) to Core 1-a (17.9 g, 54.54 mmol) and reflux for 6 hours. After the reaction is completed, the temperature of the reactant is cooled to room temperature, and o-DCB is removed. The resulting organics were separated using a silicagel column to give 12.6 g (78%) of the product.

Synthesis of Core 1-c

Core 1-b (12.5 g, 42.21 mmol) in 1-chloro-2-iodobenzene (15.10 g, 63.31 mmol), Cu powder (0.27 g, 4.22 mmol), K ₂ CO ₃ (17.50 g, 126.62 mmol), 18 -Crown-6 (2.23 g, 8.44 mmol) and nitrobenzene (150 ml) are added and refluxed for 12 hours. At the end of the reaction, the reactant is cooled to room temperature and nitrobenzene is removed. Extracted with MC and washed with water. The organic layer was dried over MgSO ₄ , concentrated, and the resulting organic was separated using a silicagel column to give 11.5 g (67%) of product.

Synthesis of Core 1-d

Core 1-c (11.5 g, 28.28 mmol) in 2-chloroaniline (4.33 g, 33.93 mmol), Pd 2 (dba) 3 (0.78 g, 0.85 mmol), tri- tert -butylphosphine (P (t-bu) 3 ) (0.57 g, 2.83 mmol), sodium tert-butoxide (t-BuONa) (8.15 g, 84.83 mmol) and toluene (150 mL) were added and stirred at 50 ° C for 6 hours. At the end of the reaction, the reaction was cooled to room temperature, extracted with EA and washed with water. The organic layer was dried over MgSO ₄ , concentrated and the resulting organic was separated using a silicagel column to give 9.9 g (77%) of product.

Synthesis of Core 1

Core 1-d (6.0 g, 13.23 mmol) in Pd (OAc) ₂ (0.30 g, 1.32 mmol), P (t-Bu) ₃ (0.77 g, 2.65 mmol), K ₂ CO ₃ (10.97 g, 79.41 mmol ), DMA (100 ml) was added and refluxed at 170 ℃ for 12 hours. 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 was dried over MgSO ₄ , concentrated and the resulting organic was separated using a silicagel column to give 2.11 g (42%) of the product.

2. Core 2의 2. Core 2 합성예Synthesis Example

Synthesis of Core 2-a

2,7-Dibromonaphthalene (33 g, 115.40 mmol) to (2-nitrophenyl) boronic acid (19.26 g, 115.40 mmol), Pd (PPh ₃ ) ₄ (4.00 g, 3.45 mmol), K ₂ CO ₃ (47.85 g, 346.19 mmol), THF (300 ml), H ₂ O (150 ml) were obtained using 18.9 g (50%) of the product using the synthesis method of Core 1-a.

Synthesis of Core 2-b

Core 2-a (18.9 g, 57.59 mmol), triphenylphosphine (37.76 g, 143.98 mmol) and o-dichlorobenzene (o-DCB) (150 ml) were synthesized using the synthesis method of Core 1-b to obtain 13.8 g (81%) of the product. )

Synthesis of Core 2-c

Core 2-b (13.8 g, 46.59 mmol), 1-chloro-2-iodobenzene (16.67 g, 69.89 mmol), Cu powder (0.30 g, 4.66 mmol), K ₂ CO ₃ (19.32 g, 139.78 mmol), 18 -Crown-6 (2.46 g, 9.32 mmol) and nitrobenzene (150 ml) were obtained using the synthesis method of Core 1-c to obtain 13.4 g (71%) of the product.

Synthesis of Core 2-d

Core 2-c (13.4 g, 32.95 mmol), 2-chloroaniline (5.04 g, 39.54 mmol), Pd ₂ (dba) ₃ (0.91 g, 0.99 mmol), P (t-bu) ₃ ) (0.67 g, 3.29 mmol), t-BuONa (9.50 g, 98.84 mmol) and toluene (150 mL) were obtained using the synthesis method of Core 1-d to give 10.1 g (73%) of the product.

Synthesis of Core 2

Core 2-d (10.0 g, 13.23 mmol), Pd (OAc) ₂ (0.50 g, 2.21 mmol), P (t-Bu) ₃ (1.28 g, 4.41 mmol), K ₂ CO ₃ (18.29 g, 132.34 mmol ), DMA (150 ml) was obtained using the synthesis method of Core 1 to obtain 4.28 g (51%) of the product.

3. Core 3의 3.Core 3 합성예Synthesis Example

Synthesis of Core 3

Core 2-d (15.0 g, 33.09 mmol), Pd (OAc) ₂ (0.74 g, 3.31 mmol), P (t-Bu) ₃ (1.92 g, 6.62 mmol), K ₂ CO ₃ (27.44 g, 198.51 mmol ), DMA (200 ml) was obtained 1.5 g (12%) of the product using the synthesis method of Core 1

4. Core 4의 4.Core 4 합성예Synthesis Example

Synthesis of Core 4

Core 1-d (20.0 g, 44.11 mmol), Pd (OAc) ₂ (0.99 g, 4.41 mmol), P (t-Bu) ₃ (2.56 g, 8.82 mmol), K ₂ CO ₃ (36.58 g, 264.68 mmol ), DMA (300 ml) was obtained 1.5 g (9%) of the product using the synthesis method of Core 1 above.

5. Core 5의 5. Core 5 합성예Synthesis Example

Synthesis of Core 5-a

2,7-Dibromonaphthalene (25 g, 87.42 mmol) to (2-nitrophenyl) boronic acid (32.11 g, 192.33 mmol), Pd (PPh ₃ ) ₄ (5.05 g, 9.62 mmol), K ₂ CO ₃ (48.33 g, 349.69 mmol), THF (300 ml), H ₂ O (150 ml) were obtained using the synthesis method of Core 1-a to give 27.2 g (84%) of the product.

Synthesis of Core 5-b

Core 5-a (27.2 g, 73.44 mmol), triphenylphosphine (96.32 g, 367.21 mmol), o-dichlorobenzene (o-DCB) (250 ml) was obtained using 16.6 g (74%) of the product using the synthesis method of Core 1-b. )

Synthesis of Core 5-c

Core 5-b (16.6 g, 54.18 mmol), 1-chloro-2-iodobenzene (14.21 g, 59.60 mmol), Cu powder (0.34 g, 5.42 mmol), K ₂ CO ₃ (22.47 g, 162.55 mmol), 18 -Crown-6 (2.86 g, 10.84 mmol) and nitrobenzene (150 ml) were obtained using the synthesis method of Core 1-c to obtain 10.4 g (46%) of the product.

Synthesis of Core 5

Core 5-c (8.0 g, 19.19 mmol), Pd (OAc) ₂ (0.22 g, 0.96 mmol), P (t-Bu) ₃ (0.56 g, 1.92 mmol), K ₂ CO ₃ (7.96 g, 57.57 mmol ), DMA (100 ml) was obtained 6.0 g (82%) of the product using the synthesis method of Core 1 above.

6. Core 6의 6.Core 6 합성예Synthesis Example

Synthesis of Core 6-a

2,6-Dibromonaphthalene (30 g, 104.91 mmol) to (2-nitrophenyl) boronic acid (38.53 g, 230.79 mmol), Pd (PPh ₃ ) ₄ (6.06 g, 11.54 mmol), K ₂ CO ₃ (58.00 g, 419.62 mmol), THF (300 ml), H ₂ O (150 ml) were obtained using the synthesis method of Core 1-a to give 34.2 g (88%) of the product.

Synthesis of Core 6-b

Core 6-a (34 g, 91.80 mmol), triphenylphosphine (120.39 g, 459.01 mmol), o-dichlorobenzene (o-DCB) (300 ml) was purified using 19.1 g (68%) of the product using the synthesis method of Core 1-b. )

Synthesis of Core 6-c

Core 6-b (19.1 g, 62.34 mmol), 1-chloro-2-iodobenzene (16.35 g, 68.58 mmol), Cu powder (0.40 g, 6.23 mmol), K ₂ CO ₃ (25.85 g, 187.03 mmol), 18 -Crown-6 (3.30 g, 12.47 mmol) and nitrobenzene (200 ml) were obtained using the synthesis method of Core 1-c to obtain 10.4 g (40%) of the product.

Synthesis of Core 6

Core 6-c (9.4 g, 22.55 mmol), Pd (OAc) ₂ (0.25 g, 1.13 mmol), P (t-Bu) ₃ (0.65 g, 2.25 mmol), K ₂ CO ₃ (9.35 g, 67.64 mmol ), DMA (150 ml) was obtained 7.2 g (84%) of the product using the synthesis method of Core 1 above.

7. Core 7의 7. Core 7 합성예Synthesis Example

Synthesis of Core 7-a

2,6-Dibromonaphthalene (42 g, 146.87 mmol) to (2-nitrophenyl) boronic acid (24.52 g, 146.87 mmol), Pd (PPh ₃ ) ₄ (5.09 g, 4.41 mmol), K ₂ CO ₃ (60.90 g, 440.61 mmol), THF (500 ml), H ₂ O (200 ml) were obtained using the synthesis method of Core 1-a to give 23.6 g (49%) of the product.

Synthesis of Core 7-b

Core 7-a (22 g, 64.04 mmol), triphenylphosphine (43.96 g, 167.60 mmol), o-dichlorobenzene (o-DCB) (200 ml) was obtained using 17.67 g (89%) of the product using the synthesis method of Core 1-b. )

Synthesis of Core 7-c

Core 7-b (15.0 g, 50.65 mmol), 1,2-diiodobenzene (15.04 g, 45.58 mmol), Cu powder (0.32 g, 5.06 mmol), K ₂ CO ₃ (21.00 g, 151.94 mmol), 18-Crown -6 (2.68 g, 10.13 mmol) and nitrobenzene (200 ml) were obtained using the synthesis method of Core 1-c to obtain 10.6 g (42%) of the product.

Synthesis of Core 7-d

Core 7-c (10.5 g, 21.08 mmol), Pd (OAc) ₂ (0.24 g, 1.05 mmol), P (t-Bu) ₃ (0.61 g, 2.11 mmol), K ₂ CO ₃ (8.74 g, 63.23 mmol ), DMA (100 ml) was obtained using the synthesis method of Core 1 to give the product 5.7 g (73%).

Synthesis of Core 7-e

Core 7-d (9.0 g, 24.31 mmol) in bis (pinacolato) diboron (8.85 g, 31.60 mmol), PdCl ₂ (dppf) ₂ (0.99 g, 1.22 mmol), KOAc (7.16 g, 72.92 mmol), DMF ( 100 ml) was added and refluxed at 120 ° C. for 6 hours. 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 was dried over MgSO ₄ , concentrated and the resulting organic was separated using a silicagel column to give 7.8 g (77%) of the product.

Synthesis of Core 7-f

Core 7-e (9.0 g, 21.57 mmol), (5-bromo-2-iodophenyl) (methyl) sulfane (8.51 g, 25.88 mmol), Pd (PPh ₃ ) ₄ (0.75 g, 0.65 mmol), K ₂ CO ₃ (8.94 g, 64.70 mmol), THF (100 ml), H ₂ O (40 ml) were obtained using the synthesis method of Core 1-a to obtain 6.8 g (64%) of the product.

Synthesis of Core 7-g

Add hydrogen peroxide (0.86 g, 25.15 mmol) and acetic acid (50 ml) to Core 7-f (7.2 g, 16.77 mmol) and stir at room temperature for 3 hours. After the reaction was completed, neutralized by adding an aqueous NaOH solution, and filtered to obtain 6.8 g (80%) of the product.

Synthesis of Core 7-h

Add sulfuric acid (10 mL) to Core 7-g (6.0 g, 11.80 mmol) and stir at room temperature for 5 hours. After the reaction was completed, neutralized with NaOH aqueous solution, and filtered to obtain 3.5 g (62%) of the product.

Synthesis of Core 7

Core 7-h (4.0 g, 8.40 mmol), bis (pinacolato) diboron (3.06 g, 10.92 mmol), PdCl ₂ (dppf) ₂ (0.34 g, 0.42 mmol), KOAc (2.47 g, 25.19 mmol), DMF ( 80 ml) was obtained using the synthesis method of Core 7-e to obtain 3.2 g (73%) of the product.

8. Core 8의 8. Core 8 합성예Synthesis Example

Synthesis of Core 8-a

Core 7-e (13 g, 31.15 mmol) in 2,4-dibromophenol (9.42 g, 37.38 mmol), Pd (PPh ₃ ) ₄ (1.08 g, 0.93 mmol), K ₂ CO ₃ (12.92 g, 93.45 mmol) , THF (150 ml), EtOH (80 ml), H ₂ O (80 ml) were obtained using the synthesis method of Core 1-a to obtain 7.9 g (55%) of the product.

Synthesis of Core 8-b

Core 8-b (7 g, 15.14 mmol), Pd (OAc) ₂ (0.17 g, 0.76 mmol), 3-nitropyridine (0.09 g, 0.76 mmol), BzOOtBu (tert-butyl peroxybenzoate) (5.88 g, 30.28 mmol) , C ₆ F ₆ (hexafluorobenzene) (100 ml) and DMI (N, N'-dimethylimidazolidinone) (70 ml) were added and refluxed at 90 ° C for 3 hours. After the reaction is completed, the temperature of the reactant is cooled to room temperature, extracted with EA, and washed with water. The organic layer was dried over MgSO ₄ , concentrated and the resulting organic was separated using a silicagel column to give 2.7 g (39%) of the product.

Synthesis of Core 8

Core 8-b (2.2 g, 4.78 mmol), bis (pinacolato) diboron (1.74 g, 6.21 mmol), PdCl ₂ (dppf) ₂ (0.20 g, 0.24 mmol), KOAc (1.41 g, 14.34 mmol), DMF ( 50 ml) was used to synthesize 1.7 g (71%) of the product.

9. Core 9의 9.Core 9 합성예Synthesis Example

Synthesis of Core 9-a

Core 7-e (11 g, 26.36 mmol) in methyl 5-bromo-2-iodobenzoate (8.99 g, 26.36 mmol), Pd (PPh ₃ ) ₄ (0.91 g, 0.79 mmol), K ₂ CO ₃ (10.93 g, 79.08 mmol), THF (150 ml), H ₂ O (70 ml) were synthesized using the synthesis method of Core 1-a to obtain 9.1 g (68%) of the product.

Synthesis of Core 9-b

Add Core 9-a (9 g, 17.84 mmol) and THF (200 ml), add 1.6M methylmagnesium bromide (1.34 ml) at 0 ° C, and stir 24 h at room temperature. After the reaction was completed, 1N HCl was added, stirred for 10 minutes, extracted with EA, and washed with water. The organic layer was dried over MgSO ₄ , concentrated, and the resulting organic was separated using a silicagel column to give 6.4 g (71%) of product.

Synthesis of Core 9-c

Core 9-b (8 g, 15.86 mmol) is dissolved in THF (200 ml), and slowly added 5 ml of methanesulfonic acid at 0 ° C. and stirred at room temperature for 1 hour. After the reaction was completed, add sodium carbonate aqueous solution (100 ml), stir for 10 minutes, extract with MC and wipe with water. The organic layer was dried over MgSO ₄ , concentrated, and the resulting organic was separated using a silicagel column to give 6.1 g (79%) of the product.

Synthesis of Core 9

Core 9-c (3.8 g, 7.81 mmol), bis (pinacolato) diboron (2.85 g, 10.16 mmol), PdCl ₂ (dppf) ₂ (0.32 g, 0.39 mmol), KOAc (2.30 g, 23.44 mmol), DMF ( 50 ml) was used for the synthesis of Core 7-e to obtain 3.6 g (86%) of the product.

Ⅱ. Sub 1 및 Sub 2의 예시II. Example of Sub 1 and Sub 2

Compounds belonging to Sub 1 and Sub 2 may be the following compounds, but are not limited thereto, and MASS DATA (FD-MS) of compounds belonging to Sub 1 and Sub 2 are shown in Table 1.

[표 1]TABLE 1

III. Product 합성III. Product Synthesis

1. Product 1 합성1.Product 1 Synthesis

P-1-5 P-1-5 합성예Synthesis Example

Core 1 (2.0 g, 5.26 mmol) in Sub 1-6 (1.68 g, 6.31 mmol), Pd ₂ (dba) ₃ (0.14 g, 0.16 mmol), t-BuONa (1.52 g, 15.77 mmol), P (t -bu) ₃ (0.11 g, 0.53 mmol) and toluene (60 ml) were added and refluxed for 12 hours. At the end of the reaction, the reaction was cooled to room temperature, extracted with MC, and washed with water. The organic layer was dried over MgSO ₄ , concentrated, and the resulting organic was separated using a silicagel filter to give 2.34 g (73%) of product.

P-2-14 P-2-14 합성예Synthesis Example

Core 2 (1.50 g, 3.94 mmol), Sub 1-39 (1.50 g, 4.73 mmol), Pd ₂ (dba) ₃ (0.11 g, 0.12 mmol), t-BuONa (1.14 g, 11.83 mmol), P (t -bu) ₃ (0.08 g, 0.39 mmol) and toluene (50 ml) were obtained using the synthesis method of P-1-5 to obtain 2.16 g (83%) of the product.

P-3-12 P-3-12 합성예Synthesis Example

Core 3 (1.40 g, 3.68 mmol), Sub 1-61 (1.24 g, 4.42 mmol), Pd ₂ (dba) ₃ (0.10 g, 0.11 mmol), t-BuONa (1.06 g, 11.04 mmol), P (t -bu) ₃ (0.07 g, 0.37 mmol) and toluene (50 ml) were obtained using the synthesis method of P-1-5 to obtain 1.82 g (79%) of the product.

P-4-18 P-4-18 합성예Synthesis Example

Core 4 (1.20 g, 3.15 mmol), Sub 1-1 (1.01 g, 3.78 mmol), Pd ₂ (dba) ₃ (0.09 g, 0.09 mmol), t-BuONa (0.91 g, 9.46 mmol), P (t -bu) ₃ (0.06 g, 0.32 mmol) and toluene (40 ml) were obtained using 1.43 g (74%) of the product using the above synthesis method of P-1-5.

P-5-12 P-5-12 합성예Synthesis Example

Core 5 (2.50 g, 6.57 mmol), Sub 1-27 (1.90 g, 7.89 mmol), Pd ₂ (dba) ₃ (0.18 g, 0.20 mmol), t-BuONa (1.89 g, 19.71 mmol), P (t -bu) ₃ (0.13 g, 0.66 mmol) and toluene (50 ml) were obtained using the synthesis method of P-1-5 to give 3.10 g (77%) of the product.

P-6-6 P-6-6 합성예Synthesis Example

Core 6 (2.40 g, 6.31 mmol), Sub 1-25 (2.63 g, 7.57 mmol), Pd ₂ (dba) ₃ (0.17 g, 0.19 mmol), t-BuONa (1.82 g, 18.92 mmol), P (t -bu) ₃ (0.13 g, 0.63 mmol) and toluene (50 ml) were obtained using 3.70 g (85%) of the product using the synthesis method of P-1-5.

2. Product 2 합성2.Product 2 Synthesis

P-6-25 P-6-25 합성예Synthesis Example

Core 7 (3.0 g, 5.73 mmol), Sub 1-6 (1.83 g, 6.88 mmol), Pd (PPh ₃ ) ₄ (0.20 g, 0.17 mmol), K ₂ CO ₃ (2.38 g, 17.20 mmol), THF ( 80 ml), H ₂ O (20 ml) were used to synthesize 2.5 g (69%) of the product using the synthesis method of Core 1-a.

P-6-23 P-6-23 합성예Synthesis Example

Core 8 (2.2 g, 4.43 mmol), Sub 1-50 (1.28 g, 4.43 mmol), Pd (PPh ₃ ) ₄ (0.15 g, 0.13 mmol), K ₂ CO ₃ (1.80 g, 13.01 mmol), THF ( 60 ml), H ₂ O (20 ml) was used to synthesize 2.3 g (83%) of the product using the synthesis method of Core 1-a.

P-6-21 P-6-21 합성예Synthesis Example

Core 9 (2.9 g, 5.44 mmol), Sub 1-1 (1.45 g, 5.44 mmol), Pd (PPh ₃ ) ₄ (0.19 g, 0.16 mmol), K ₂ CO ₃ (2.25 g, 16.32 mmol), THF ( 70 ml), H ₂ O (25 ml) using the synthesis method of Core 1-a to give 2.7 g (79%) of the product.

FD-MS values of the compounds P-1-1 to P-6-25 of the present invention prepared according to the synthesis examples as described above are shown in Table 2 below.

[표 2]TABLE 2

유기전기소자의 제조평가Manufacturing Evaluation of Organic Electrical Device

[[ 실시예Example 1] One] 레드유기전기발광소자Red organic electroluminescent device (인광호스트)Phosphorescent Host

First, on the ITO layer (anode) formed on the glass substrate, N ^1- (naphthalen-2-yl) -N ⁴ , N ⁴ -bis (4- (naphthalen-2-yl (phenyl) amino) phenyl) -N ^1- A phenylbenzene-1,4-diamine (hereinafter abbreviated as 2-TNATA) film was vacuum deposited to form a hole injection layer having a thickness of 60 nm. Subsequently, a hole transporting material of 4,4-bis [ N- (1-naphthyl) -N -phenylamino] biphenyl (hereinafter abbreviated as -NPB) was vacuum deposited to a thickness of 60 nm on the hole injection layer. A transport layer was formed. 95: 5 using compound P-1-1 of the present invention as a host material on the hole transport layer and (piq) ₂ Ir (acac) [bis- (1-phenylisoquinolyl) iridium (III) acetylacetonate] as a dopant material Doping by weight to form a light emitting layer of 30nm thickness. On the light emitting layer, (1,1'-bisphenyl) -4-oleito) bis (2-methyl-8-quinoline oleito) aluminum (hereinafter abbreviated as BAlq) was vacuum-deposited to a thickness of 10 nm. A blocking layer was formed, and tris (8-quinolinol) aluminum (hereinafter abbreviated as Alq ₃ ) was deposited to a thickness of 40 nm on the hold layer 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 an organic electroluminescent device.

[[ 실시예Example 2] 내지 [ 2] to [ 실시예Example 31] 31] 레드유기전기발광소자Red organic electroluminescent device

An organic electroluminescent device was manufactured according to the same method as Example 1 except for using the compound of the present invention shown in Table 3 instead of the compound P-1-1 according to the embodiment of the present invention as a red host material of the emission layer. It was.

[[ 비교예Comparative example 1] 내지 [ 1] to [ 비교예Comparative example 5] 5]

An organic electroluminescent device was manufactured in the same manner as in Example 1, except that one of Comparative Compounds A to E was used instead of Compound P-1-1 according to the embodiment of the present invention as a host material of the emission layer. It was.

The electroluminescence (EL) characteristics of the photoresearch company PR-650 were applied by applying a forward bias DC voltage to each of the organic electroluminescent devices of Examples 1-31 and Comparative Examples 1-5 prepared as described above. The T95 life was measured using a lifespan measuring instrument manufactured by McScience Inc. at 2500 cd / m ² reference brightness, as shown in Table 3 below.

[표 3]TABLE 3

As can be seen from the results of Table 3, the organic electroluminescent device using the organic electroluminescent device material of the present invention as a phosphorescent host significantly improved luminous efficiency and lifespan, and exhibited low driving voltage.

In more detail, when the comparative compounds B to E having indolocarbazole as the main skeleton as the host skeleton were used as host materials, the device characteristics were superior to those of the comparative compounds B to E. When the compound of the present invention was used as a host material, it showed better results in terms of driving voltage, efficiency and lifetime.

Comparing Comparative Examples 2-5 using Comparative Compounds B to E, Comparative Compounds B and C in which indole was fused to an indolocarbazole skeleton were benzothiophen or benzofuran. It was confirmed that (benzofuran) showed better device characteristics than fused comparative compounds D and E, but rather carbazole and dibenzothiophene in indolocarbazole skeletons. It can be seen that the compound of the present invention, which is fused with dibenzofuran or fluorene, shows remarkably excellent device characteristics.

This is because the physical properties of the compound are significantly changed as phenyl is further fused into the core as shown in Table 4 below. Comparing the physical properties of the compound of Comparative Compound C and the compound P-1-5 of the present invention, the difference in the energy level of the compound, in particular HOMO level, T1 level can be confirmed, and the compound of the present invention is more red than It can be seen that the physical properties suitable for the host. Therefore, the difference in physical properties of such compounds acts as a major factor (eg, energy balance) in improving device performance during device deposition, resulting in different device results.

[표 4]TABLE 4

The above description is merely illustrative of the present invention, and those skilled in the art will appreciate that various modifications can 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.

CROSS-REFERENCE TO RELATED APPLICATIONCROSS-REFERENCE TO RELATED APPLICATION

This patent application is filed with the U.S. Patent No. 10-2016-0104136 filed in Korea on August 17, 2016, Articles 119-121, 365 (35 USC §19-§121, §365 ), The contents of which are hereby incorporated by reference in their entirety. In addition, if this patent application claims priority for the same reason for countries other than the United States, all its contents are incorporated into this patent application by reference.

Claims

Compound represented by the following formula (1):

<Formula 1>

In Chemical Formula 1,

Ring A is one of the following Chemical Formulas 1-1 to 1-3,

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

R 1 -R 17 are, independently from each other, hydrogen; heavy hydrogen; halogen; C 6 ~ C 60 Aryl group; Fluorenyl group; C 2 -C 60 heterocyclic group containing at least one hetero atom of O, N, S, Si and P; A fused ring group of an aromatic ring of C 6 ~ C 60 and an aliphatic ring 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 alkoxyl group; C 6 -C 30 aryloxy group; And -L'-N (R a ) (R b ); selected from the group consisting of, adjacent groups can combine with each other to form a ring,

X is N (-L 1 -Ar 1 ), O, S or C (R ') (R "),

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; And C 3 ~ fused ring group of an aromatic ring of C 60 of aliphatic rings and C 6 ~ C 60; is selected from the group consisting of,

Ar 1 is a C 6 ~ C 60 An aryl group; Fluorenyl group; C 2 ~ C 60 heterocyclic group containing at least one heteroatom of O, N, S, Si and P; Fused ring group of an aromatic ring of C 3 ~ C 60 of aliphatic rings and C 6 ~ C 60; And -L'-N (R a ) (R b );

R ′ and R ″ are each independently of the C 1 to C 50 alkyl group; C 6 to C 60 aryl group; fluorenyl group; C 2 containing at least one hetero atom of O, N, S, Si and P A heterocyclic group of ~ C 60 ; and a fused ring group of an aromatic ring of C 6 ~ C 60 and an aliphatic ring of C 3 ~ C 60 , R 'and R "may be bonded to each other to form a ring And

R a and R b are each independently a C 6 ~ C 60 aryl group; Fluorenyl group; C 2 ~ C 60 heterocyclic group containing at least one heteroatom of O, N, S, Si and P; And a fused ring group of C 3 ~ C 60 aliphatic ring and C 6 ~ C 60 aromatic ring, R a and R b may be bonded to each other to form a ring,

R 1 to R 17 , Ar 1 , R ′, R ″, R a , R b , L ′ and L 1 are an aryl group, fluorenyl group, heterocyclic group, fused ring group, alkyl group, alkenyl group, alkynyl group , An alkoxyl group, an aryloxy group, an arylene group or a fluorenylene group, each of which is deuterium; halogen; a silane group unsubstituted or substituted with an alkyl group of C 1 -C 20 or an aryl group of C 6 -C 20 ; ; boron group; germanium group; cyano group; nitro group; C 1 -C 20 alkylthio Sy of; an alkoxy group of C 1 -C 20; C 1 -C 20 alkyl group; an alkenyl group of C 2 -C 20; C alkynyl of 2 -C 20; an aryl group of C 6 -C 20 substituted with heavy hydrogen;; an aryl group of C 6 -C 20 fluorenyl group; O, N, S, at least one selected from the group consisting of Si and P C 2 -C 20 heterocyclic group containing a hetero atom of; C 3 -C 20 cycloalkyl group; C 7 -C 20 arylalkyl group; and C 8 -C 20 arylalkenyl group selected from the group consisting of More than one substitution May be further substituted with a group.
The method of claim 1,

Formula 1 is a compound, characterized in that represented by any one of the following formula (2):

<Formula 2> <Formula 3> <Formula 4>

<Formula 5> <Formula 6> <Formula 7>

In Formulas 2 to 7, R 1 to R 17 and X are the same as defined in claim 1.
The method of claim 1,

Formula 1 is a compound, characterized in that represented by any one of the following formula 8-1 to formula 11-6:

<Formula 8-1> <Formula 8-2> <Formula 8-3>

<Formula 8-4> <Formula 8-5> <Formula 8-6>

  <Formula 9-1> <Formula 9-2> <Formula 9-3>

<Formula 9-4> <Formula 9-5> <Formula 9-6>

      <Formula 10-1> <Formula 10-2> <Formula 10-3>

<Formula 10-4> <Formula 10-5> <Formula 10-6>

    <Formula 11-1> <Formula 11-2> <Formula 11-3>

  <Formula 11-4> <Formula 11-5> <Formula 11-6>

In Chemical Formulas 8-1 to 11-6, R 1 to R 17 are the same as defined in claim 1.
The method of claim 1,

Formula 1 is a compound characterized in that one of the following compounds:

.
A first electrode; Second electrode; And an organic material layer formed between the first electrode and the second electrode.

The organic material layer is an organic electroluminescent device comprising the compound of claim 1.
The method of claim 5,

The compound is included in at least one of a hole injection layer, a hole transport layer, a light emitting auxiliary layer, a light emitting layer, an electron transport auxiliary layer, an electron transport layer and an electron injection layer of the organic material layer,

The compound is an organic electric device, characterized in that used as a single compound or a mixture of two or more.
The method of claim 6,

The compound of claim 1, wherein the compound is included in the light emitting layer.
The method of claim 5,

The organic material layer is formed by a spin coating process, a nozzle printing process, an inkjet printing process, a slot coating process, a dip coating process or a roll-to-roll process.
The method of claim 5,

And an optical efficiency improvement layer formed on a surface opposite to the organic material layer on both surfaces of the first electrode or on a surface opposite to the organic material layer on both surfaces of the second electrode.
A display device comprising the organic electroluminescent device of claim 5; And

And a controller for driving the display device.
The method of claim 10,

The organic electronic device is an electronic device, characterized in that one of an organic electroluminescent device, an organic solar cell, an organic photoconductor, an organic transistor, and a device for monochrome or white illumination.