KR20200082086A - Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof - Google Patents

Abstract

The present invention provides: an organic electric element comprising a compound represented by chemical formula 1, a first electrode, a second electrode, and an organic material layer disposed between the first electrode and the second electrode; and an electronic device comprising the organic electric element. By comprising the compound represented by chemical formula 1 in the organic material layer, it is possible to lower a driving voltage, and improve luminous efficiency and a lifespan of the organic electric element.

Description

Compounds for organic electrical devices, organic electrical devices using the same, and electronic devices thereof {COMPOUND FOR ORGANIC ELECTRONIC ELEMENT, ORGANIC ELECTRONIC ELEMENT USING THE SAME, AND AN ELECTRONIC DEVICE THEREOF}

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

In general, the organic light emitting phenomenon refers to a phenomenon that converts 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 and a cathode and an organic material layer therebetween. Here, the organic material layer is often composed of a multi-layer structure composed of different materials in order to increase the efficiency and stability of the organic electric device, and may be formed of, for example, 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 electrical device may be classified into light emitting materials and charge transport materials, such as hole injection materials, hole transport materials, electron transport materials, and electron injection materials, depending on their function. In addition, the light-emitting material may be classified into a polymer type and a low-molecular type according to the molecular weight, and a fluorescent material derived from the singlet excited state of the electron and a phosphorescent material derived from the triplet excited state of the electron according to the light emission mechanism. have. In addition, the luminescent material may be divided into blue, green, and red luminescent materials and yellow and orange luminescent materials necessary for realizing a better natural color according to the luminous color.

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

Currently, the size of the portable display market is increasing as a large-area display, and accordingly, power consumption greater than that required in the existing portable display is required. Therefore, power consumption has become a very important factor for a portable display that has a limited power supply, such as a battery, and the efficiency and lifespan problems must also be solved.

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

Therefore, there is a need to develop a light emitting material that has high thermal stability and can efficiently achieve charge balance in the light emitting layer. That is, in order to sufficiently exhibit the excellent characteristics of the organic electric device, materials constituting an 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, are supported by stable and efficient materials It should be preceded, but the development of a stable and efficient organic material layer material for an organic electric device has not been sufficiently made, and among them, development of a host material of a light emitting layer is urgently required.

An object of the present invention is to provide a compound capable of lowering the driving voltage of a device and improving the luminous efficiency and life of the device, an organic electrical device using the same, and its electronic device.

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

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

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

1 is an exemplary view of an organic electroluminescent device according to the present invention.
2 is a chemical formula according to an embodiment of the present invention.

The terms "aryl group" and "arylene group" used in the present invention have 6 to 60 carbon atoms, respectively, and are not limited thereto unless otherwise specified. In the present invention, an aryl group or an arylene group may include a monocyclic, ring aggregate, several conjugated ring systems, spiro compounds, and the like. In addition, unless otherwise specified herein, the aryl group may include a fluorenyl group and the arylene group may include a fluorenylene group.

The term "fluorenyl group" or "fluorenylene group" used in the present invention means a monovalent or divalent functional group in which R, R'and R" are both hydrogen in the following structures, unless otherwise specified. Substituted fluorenyl group" or "substituted fluorenylene group" means that at least one of the substituents R, R', R" is a substituent other than hydrogen, and R and R'are bonded to each other to form a bonded carbon. It includes the case where a compound was formed as a spy together.

The term "spyro compound" as used in the present invention has a'spyro linkage', and a spiro linkage refers to a linkage formed by two rings sharing only one atom. At this time, the atoms shared by the two rings are called'spyro atoms', and these are'monospyro-','dispiro-', and'trispyro' depending on the number of spy atoms in a compound. It is called a compound.

The term "heterocyclic group" used in the present invention includes aromatic rings such as "heteroaryl group" or "heteroarylene group" as well as non-aromatic rings, and carbon atoms each containing one or more heteroatoms unless otherwise specified. It means a ring of 2 to 60, but is not limited thereto. The term "heteroatom" as used herein refers to N, O, S, P or Si unless otherwise specified, and the heterocyclic group is a monocyclic, ring aggregate, heterozygous multiple ring system, spy containing heteroatoms. Means a compound and the like.

The term "heterocyclic group" used in the present invention means a ring containing a heteroatom such as N, O, S, P or Si instead of carbon forming a ring, and "heteroaryl group" or "heteroarylene group" In addition to the aromatic ring as well as non-aromatic ring, a compound containing a heteroatom group such as SO ₂ , P=O, etc. may be included instead of carbon forming a ring.

The term "aliphatic ring group" used in the present invention means a cyclic hydrocarbon excluding aromatic hydrocarbons, and includes monocyclic, ring aggregates, conjugated multiple ring systems, spiro compounds, and the like, unless otherwise specified. It means a 3 to 60 ring, but is not limited thereto. For example, even when the aromatic ring benzene and the non-aromatic ring cyclohexane are fused, it corresponds to the aliphatic ring.

In the present specification, the'group name' corresponding to an aryl group, an arylene group, a heterocyclic group, etc. exemplified as examples of each symbol and its substituent may describe'the name of a group reflecting a singer', but is described as a'parent compound name' You may. For example, in the case of'phenanthrene', which is a type of aryl group, the monovalent'group' is'phenanthryl' and the bivalent group is a singular such as'phenanthrylene', but the name of the group can be described. Regardless, the parent compound name may be described as'phenanthrene'. Similarly, in the case of pyrimidine, it can be described as'pyrimidine' regardless of the singer, or in the case of monovalent pyrimidinyl group, in the case of divalent pyrimidinylene, etc., as the'group name' of the corresponding singer. have.

In addition, in this specification, in describing the compound name or the substituent name, a number, an alphabet, or the like indicating the position may be omitted. For example, pyrido[4,3-d]pyrimidine as pyridopyrimidine, benzofuro[2,3-d]pyrimidine as benzofuropyrimidine, 9,9-dimethyl-9H-flu Oren can be described as dimethylfluorene or the like. Therefore, both benzo[g]quinoxaline and benzo[f]quinoxaline can be described as benzoquinoxaline.

In addition, unless expressly stated, the formula used in the present invention is applied in the same manner as the definition of a substituent based on the index definition of the following formula.

Here, when a is an integer of 0, the substituent R ¹ means non-existent, that is, when a is 0, it means that hydrogen is bonded to all of the carbons forming the benzene ring. The formula or compound may be omitted. In addition, when a is an integer of 1, one substituent R ¹ is bound to any one of carbons forming a benzene ring, and when a is an integer of 2 or 3, for example, it can be bonded as follows, and a is 4 to 6 Even in the case of an integer, it binds to the carbon of the benzene ring in a similar manner, and when a is an integer of 2 or more, R ¹ may be the same or different.

In addition, unless otherwise specified in the present specification, the rings formed by bonding with adjacent groups are C ₆ ~ C ₆₀ aromatic ring groups; Fluorenyl group; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₃ ~ C ₆₀ aliphatic ring group; C ₃ ~ C ₆₀ aliphatic ring and C ₆ ~ C ₆₀ aromatic ring fused ring group; And combinations thereof.

Hereinafter, a stacked 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 detailed descriptions of related known configurations or functions may obscure the subject matter of the present invention, detailed descriptions thereof will be omitted.

Also, 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 "directly above", but also with another component in the middle. It should be understood that the case may be included. Conversely, it should be understood that when a component is said to be “just above” another part, it means that there is no other part in between.

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 includes a first electrode 120, a second electrode 180, and a first electrode 120 formed on a substrate 110. Between the second electrode 180 includes an organic material layer containing the compound according to the present invention. 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 material 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 sequentially stacked on the first electrode 120. . At this time, 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, etc., and the electron transport layer 160, etc. It can also serve as a hole blocking layer.

In addition, although not shown, the organic electric 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 of both surfaces of the first electrode that does not contact the organic material layer or a surface of both surfaces of the second electrode that does not contact the organic material layer.

The 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 of the light-emitting layer 150, or may be used as a material for a light efficiency improving layer, but preferably, the compound according to Formula 1 of the present invention is used as a host of the light-emitting layer.

On the other hand, even in the case of the same core, the band gap, electrical characteristics, and interfacial characteristics may vary depending on which substituent is attached to which position, and thus, the selection of the core and the combination of sub-substituents coupled thereto. It is necessary to study, especially when the energy level and T ₁ value between each organic material layer and the intrinsic properties of materials (mobility, interfacial properties, etc.) are optimally combined, long life and high efficiency can be achieved simultaneously.

Therefore, in the present invention, by using the compound represented by the formula (1) as a host of the light emitting layer, the energy level and T ₁ value between each organic material layer, the properties of the material (mobility, interfacial properties, etc.) are optimized to optimize the life of the organic electric device. And efficiency can be improved 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, by depositing a metal or conductive metal oxide or an alloy thereof on a substrate to form an anode 120, and a hole injection layer 130 thereon , After 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, can be prepared by 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 the 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 process or a solvent process (e.g., spin coating process), nozzle printing process, inkjet printing process, slot coating process, dip coating process, roll-to-roll process, doctor blade using various polymer materials It can be produced with fewer layers by a method such as a ding process, a screen printing process, or a 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 formation method.

The organic electric device according to an embodiment of the present invention may be a front emission type, a back emission type, or a double-sided emission type depending on the 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 photoreceptor, an organic transistor, a monochromatic lighting device and a quantum dot display device.

Another embodiment of the present invention may include an electronic device including a display device including the above-described organic electric element of the present invention and a control unit for controlling the display device. At this time, the electronic device may be a current or future wired/wireless communication terminal, and includes all electronic devices such as mobile communication terminals such as mobile phones, PDAs, electronic dictionaries, PMPs, remote controls, navigation, game machines, various TVs, and various computers.

Hereinafter, a compound according to an aspect of the present invention will be described.

The compound according to an aspect of the present invention is represented by Formula 1 below.

<Formula 1>

In Chemical Formula 1, each symbol may be defined as follows.

X and Y are independently of each other N-(L-Ar).

n and m are each 0 or 1, and n+m is an integer of 1 or more.

R ¹ to R ⁴ are independently of each other hydrogen; heavy hydrogen; halogen; Cyano group; 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; C ₃ ~ C ₆₀ aliphatic 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 ₃₀ Aryloxy group; And -L'-N(R _a )(R _b ); is selected from the group consisting of, adjacent R ² , neighboring R ³ , neighboring R ⁴ , R ¹ and R ³ , R ² and R ³ , R ² and R ³ , or R ³ and R ⁴ may combine with each other to form a ring.

However, when m is 1, adjacent groups are bonded to each other to form a ring. For example, it may be m the form one of the case, the adjacent R ² to each other, the adjacent R ⁴ together, R ¹ and R ³ together, R ² and R ³ together, or R ³ and R ⁴ ring by combining to each other, . The ring formed at this time is C ₆ ~ C ₆₀ aromatic hydrocarbons; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; C ₃ ~ C ₆₀ aliphatic ring group; And combinations thereof. For example, when adjacent groups are combined with each other to form an aromatic hydrocarbon, preferably C ₆ ~ C ₃₀ aromatic hydrocarbons, more preferably C ₆ ~ C ₁₄ aromatic hydrocarbons, such as benzene ring, naphthalene, phenanthrene, etc. Can form.

a is an integer from 0 to 2, b is an integer from 0 to 4, c is an integer from 0 to 2, d is an integer from 0 to 2, and each of these is an integer of 2 or more, each of a plurality of R ¹ and a plurality of R ² Each of each of the plurality of R ^{3 s, and} each of the plurality of R ^{4 s} are the same as or different from each other.

When R ¹ to R ⁴ are aryl groups, preferably, C ₆ to C ₃₀ aryl groups, more preferably C ₆ to C ₁₈ aryl groups, such as phenyl, biphenyl, naphthyl, terphenyl, and the like.

When R ¹ to R ⁴ are heterocyclic groups, preferably, they may be C ₂ to C ₃₀ heterocyclic groups, more preferably C ₂ to C ₂₄ heterocyclic groups, such as triazine, carbazole, Phenylcarbazole, biphenylcarbazole, naphthylcarbazole, dibenzothiophene, dibenzofuran, and the like.

When R ¹ to R ⁴ are alkoxy groups, they are preferably C ₁ to C ₁₀ alkoxy groups and may be, for example, methoxy, ethoxy, and the like.

L and L'are each independently a single bond; C ₆ ~ C ₆₀ Arylene group; Fluorylene group; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; And C ₃ ~ C ₆₀ It may be selected from the group consisting of an aliphatic ring group.

When L and L'are arylene groups, preferably an arylene group of C ₆ to C ₃₀ , more preferably an arylene group of C ₆ to C ₁₈ , such as phenylene, naphthalene, biphenyl, terphenyl, and the like.

When L and L'are heterocyclic groups, it is preferably a C ₂ to C ₃₀ heterocyclic group, more preferably a C ₂ to C ₁₈ heterocyclic group, such as triazine, pyrimidine, pyridine , Quinazoline, quinoxaline, benzoquinazoline, benzothienopyrimidine, benzofuropyrimidine, carbazole, phenylcarbazole, dibenzothiophene, dibenzofuran, and the like.

Ar is 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; C ₃ ~ C ₆₀ aliphatic 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 ₃₀ Aryloxy group; C ₆ ~ C ₃₀ Arylthio group; And combinations thereof.

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

When Ar is a heterocyclic group, it is preferably a C ₂ to C ₃₀ heterocyclic group, more preferably a C ₂ to C ₂₄ heterocyclic group, for example, pyridine, pyrimidine, triazine, dibenzo Thiophene, benzonaphthothiophene, dibenzofuran, benzonaphthofuran, quinazolin, benzoquinazoline, quinoxaline, benzothienopyrimidine, benzofuropyrimidine, carbazole, phenylcarbazole, biphenyl Carbazole and the like.

R _a and R _b are independently of each other 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; C ₃ ~ C ₆₀ aliphatic ring group; And combinations thereof.

Substituents indicated by each symbol may be further substituted. For example, the R ¹ ~ R ⁴ , L, Ar, L', R _a , R _b , rings formed by bonding adjacent groups to each other are 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 ; Siloxane groups; Boron group; Germanium group; Phosphine oxide unsubstituted or substituted with a C ₁ -C ₂₀ alkyl group or a C ₆ -C ₂₀ aryl group; Cyano group; Nitro group; C ₁ -C ₂₀ alkylthio; C ₁ -C ₂₀ Alkoxy group; C ₆ -C ₂₀ Arylalkoxy group; C ₁ -C ₂₀ alkyl group; Alkenyl group of C ₂ -C ₂₀ ; Alkynyl group of C ₂ -C ₂₀ ; C ₆ -C ₂₀ Aryl group; A C ₆ -C ₂₀ aryl group substituted with deuterium; Fluorenyl group; A C ₂ -C ₂₀ heterocyclic group including at least one heteroatom selected from the group consisting of O, N, S, Si and P; C ₃ -C ₂₀ aliphatic ring group; C ₇ -C ₂₀ Arylalkyl group; C ₈ -C ₂₀ Arylalkenyl group; And it may be further substituted with one or more substituents selected from the group consisting of.

Preferably, Formula 1 may be represented by Formula 2 or Formula 3 below.

<Formula 2> <Formula 3>

In Chemical Formulas 2 and 3, R ¹ to R ⁴ , L and Ar are as defined in Chemical Formula 1.

In addition, Chemical Formula 1 may be represented by one of the following Chemical Formulas 4 to 15.

<Formula 4> <Formula 5> <Formula 6>

<Formula 7> <Formula 8> <Formula 9>

<Formula 10> <Formula 11> <Formula 12>

<Formula 13> <Formula 14> <Formula 15>

In Chemical Formulas 4 to 15, L and Ar are as defined in Chemical Formula 1.

Preferably, the Ar may be represented by the following formula Ar-1 or formula Ar-2.

<Formula Ar-1> <Formula Ar-2>

In the above formulas Ar-1 and Ar-2, each symbol can be defined as follows.

Q ¹ to Q ⁹ are each independently N or C(R ^c ).

R ^c is independently of each other 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 ; Siloxane groups; Boron group; Germanium group; Phosphine oxide unsubstituted or substituted with a C ₁ -C ₂₀ alkyl group or a C ₆ -C ₂₀ aryl group; Cyano group; Nitro group; C ₁ -C ₂₀ alkylthio; C ₁ -C ₂₀ Alkoxy group; C ₆ -C ₂₀ Arylalkoxy group; C ₁ -C ₂₀ alkyl group; Alkenyl group of C ₂ -C ₂₀ ; Alkynyl group of C ₂ -C ₂₀ ; C ₆ -C ₂₀ Aryl group; Fluorenyl group; A C ₂ -C ₂₀ heterocyclic group including at least one heteroatom selected from the group consisting of O, N, S, Si and P; C ₃ -C ₂₀ aliphatic ring group; C ₇ -C ₂₀ Arylalkyl group; And C ₈ -C _{20 It} is selected from the group consisting of aryl alkenyl group, adjacent R ^c may be bonded to each other to form a ring. In addition, each R ^c may be the same or different from each other.

The Z ring may be selected from the group consisting of the following formulas Z-1 to Z-15.

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

<Formula Z-5> <Formula Z-6> <Formula Z-7> <Formula Z-8>

<Formula Z-9> <Formula Z-10> <Formula Z-11> <Formula Z-12>

<Formula Z-13> <Formula Z-14> <Formula Z-15>

In the formulas Z-1 to Z-15, each symbol may be defined as follows.

W ¹ and W ² are each independently N-(L ¹ -Ar ¹ ), S, O or C(R')(R").

V is independently of each other N or C(R ^d ). Each V is the same or different from each other.

L ¹ is a single bond; C ₆ ~ C ₆₀ Arylene group; Fluorylene group; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; And C ₃ ~ C ₆₀ It may be selected from the group consisting of an aliphatic ring group.

Ar ¹ is 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; C ₃ ~ C ₆₀ aliphatic 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 ₃₀ Aryloxy group; C ₆ ~ C ₃₀ Arylthio group; And combinations thereof.

R ^d , R'and R" are independently deuterium; halogen; a silane group unsubstituted or substituted with a C ₁ -C ₂₀ alkyl group or a C ₆ -C ₂₀ aryl group; a siloxane group; a boron group; a germanium group; an alkoxy group of _{C 1 -C 20; C 1 -C} 20 alkyl group or a C ₆ aryl group a substituted or unsubstituted phosphine oxide of the -C _20; cyano group; nitro group; an alkylthio import of C ₁ -C _20; C ₆ -C ₂₀ arylalkoxy group; C ₁ -C ₂₀ alkyl group; C ₂ -C ₂₀ alkenyl group; C ₂ -C ₂₀ alkynyl group; C ₆ -C ₂₀ aryl group; fluorenyl group; O , C ₂ -C ₂₀ heterocyclic group including at least one heteroatom selected from the group consisting of N, S, Si and P. C ₃ -C ₂₀ aliphatic ring group; C ₇ -C ₂₀ arylalkyl group; And C ₈ -C _{20 It} is selected from the group consisting of aryl alkenyl group, adjacent R ^d may be bonded to each other to form a ring, R'and R" may be bonded to each other to form a ring. In addition, a plurality of R ^d are the same or different from each other.

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

.

.

In another aspect of the present invention, the present invention provides an organic electric device including a first electrode, a second electrode, and an organic material layer formed between the first electrode and the second electrode, wherein the organic material layer is represented by Chemical Formula 1 It contains one single compound or two or more compounds.

The organic material layer includes 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, preferably the compound is included in the light emitting layer, more preferably It is used as a host material for the light emitting layer.

In another aspect of the present invention, the present invention provides an electronic device including a display device including the organic electric element represented by Chemical Formula 1 and a control unit driving the display device.

Hereinafter, examples of the synthesis of the compound represented by Chemical Formula 1 according to the present invention and the manufacturing example of the organic electric device will be specifically described with reference to Examples, but the present invention is not limited to the following Examples.

Synthetic example

The compound represented by Chemical Formula 1 according to the present invention is synthesized by reacting Core A and Sub A as shown in Reaction Scheme 1 below, but is not limited thereto.

<Scheme 1>

1.Example compounds of Core A and Synthetic example

The compound belonging to Core A of Reaction Scheme 1 may be the following compound, but is not limited thereto.

The FD-MS values of the compounds belonging to Core A are shown in Table 1 below.

[Table 1]

Core A of Reaction Scheme 1 may be synthesized by the reaction route of Reaction Scheme 2 below, but is not limited thereto.

<Reaction Scheme 2>

(1) Synthesis example of C-1

After adding ethyl 2-amino-6-bromonaphthalene-1-carboxylate (5-g, 17mmol, Cas No. 1824676-64-3) to a round bottom flask, dissolve with formamide (0.3M), and stir at 190°C for 12 hours. . When the reaction was completed, water was added to cool to room temperature, and the precipitated solid was filtered, and then separated by a silica gel column to obtain 4 g of C-1 (yield: 85%).

(2) Synthesis Example of C-2

After putting C-1 (5g, 18.2mmol) in a round bottom flask and dissolving with POCl ₃ (100ml) at room temperature, N , N -Diisopropyl ethylamine (3.5g, 27.3mmol) was slowly added dropwise and stirred at 90°C. After the reaction was completed, the intermediate product was concentrated, and then ice water (500ml) was added and stirred at room temperature for 1 hour. The resulting solid was filtered under reduced pressure and dried to obtain 3.2 g of product C-2 (yield: 60%).

(3) Synthesis example of C-3 (C-4, C-5)

C-2 (5g, 17.0mmol) was added to a round bottom flask, dissolved in THF (65ml), and then (2-nitrophenyl)boronic acid (CAS Registry Number: 5570-19-4) (3.1g, 18.7mmol), Pd( PPh ₃ ) ₄ (0.6 g, 0.5 mmol), K ₂ CO ₃ (7.1 g, 51.1 mmol), water (30 ml) was added and stirred at 90°C. After the reaction was completed, the organic layer was extracted with CH ₂ Cl ₂ and water, dried and concentrated with MgSO ₄ , and the resulting compound was separated by a silica gel column and recrystallized to obtain 4.5 g of product C-3 (yield: 79%).

C-4 4.8g (yield: 73%) and C-5 4.0g (yield: 61%) were also obtained by proceeding the reaction in the same manner as C-3.

(4) Synthesis example of C-6 (C-7, C-8)

C-3 (5g, 14.9mmol) was added to a round bottom flask, dissolved in THF (60ml), and 28% ammonia water (60ml) was added and stirred at room temperature for 20 hours. After the reaction was completed, the organic layer was extracted with CH ₂ Cl ₂ and water, dried and concentrated with MgSO ₄ , and the resulting compound was separated by a silica gel column and recrystallized to obtain 4.5 g of product C-3 (yield: 79%).

In the same manner, C-4 4.8g (yield: 73%) and C-5 4.0g (yield: 61%) were obtained.

(5) Synthesis example of C-9 (C-10, C-11)

After adding C-6 (5g, 15.8mmol) to a round bottom flask and dissolving with THF (60ml), t-butylnitirite (2.1g, 23.7mmol) was added and stirred at 80°C for 8 hours. After the reaction was completed, the organic layer was extracted with CH ₂ Cl ₂ and water, dried over MgSO ₄ and concentrated, and the resulting compound was separated by a silica gel column and recrystallized to obtain 3.0 g of product C-9 (yield: 63%).

In the same manner, C-10 2.8 g (yield: 59%) and C-11 2.4 g (yield: 50%) were obtained.

(6) Synthesis Example of Core A

Round bottom flask with C-4 (10 g, 33.2 mmol) and PPh ₃ (26.1 g, 99.6 mmol) was added and stirred at 180°C. After the reaction was completed, the organic layer was extracted with CH ₂ Cl ₂ and water, dried and concentrated with MgSO ₄ , and the resulting compound was separated by a silica gel column and recrystallized to obtain Core A-1 7.2 g (yield: 80%).

In the same manner, 5.9 g (yield: 65%) of Core A-2 and 5.5 g (yield: 60%) of Core A-3 were obtained.

2. Exemplary compounds of Sub A

The compounds belonging to Sub A may be the following compounds, but are not limited thereto.

The FD-MS values of the compounds belonging to Sub A are shown in Table 2 below.

[Table 2]

3. Final compound Synthetic example

P-11 Synthetic example

Round bottom flask with Core 1 (10g, 37.1mmol), INTER 1-1 (17.2g, 40.8mmol), Pd ₂ (dba) ₃ (1.0g, 1.1mmol), P(t-Bu)3 (0.5g, 2.2mmol), t-BuONa (10.7g, 111.4mmol) was added, dissolved in toluene, and heated to reflux. After the reaction was completed, the organic layer was extracted with CH ₂ Cl ₂ and water, dried over MgSO ₄ and concentrated to separate the resulting compound with a silica gel column, and recrystallized to obtain 14.5 g of P-11 (yield: 60%).

Synthesis Example of P-40

Core 6 (10g, 31.3mmol), INTER 1-4 (10g, 34.4mmol), Pd ₂ (dba) ₃ (0.9g, 0.9mmol), P(t-Bu)3 (0.4g, 1.9mmol), t-BuONa (9.0g, 93.9mmol), and Toluene were processed in the same manner as in the synthesis example of P-11 above. 1-40 g (yield: 80%) of P-40 was obtained.

P-68 Synthetic example

Core 7 (10g, 31mmol), INTER 1-2 (11.8g, 34.4mmol), Pd ₂ (dba) ₃ (0.9g, 0.9mmol), P(t-Bu)3 (0.4g, 1.9mmol), t-BuONa (9.0g, 93.9mmol), and Toluene were processed in the same manner as in the synthesis example of P-11 above. 12.8 g (yield: 65%) of P-69 was obtained.

P-197 Synthetic example

Core 13 (10g, 17.3mmol), INTER 1-3 (3.9g, 19.1mmol), Pd ₂ (dba) ₃ (0.5g, 0.5mmol), P(t-Bu)3 (0.2g, 1.0mmol), t-BuONa (5.0g, 52.0mmol), Toluene was processed in the same manner as in the synthesis example of P-11 5.8 g (yield: 51%) of P-197 was obtained.

The FD-MS values of the compounds P-1 to P-203 of the present invention prepared according to the above synthesis examples are shown in Table 3 below.

[Table 3]

Manufacturing evaluation of organic electric devices

[ Example 1] Green organic light emitting device (green phosphorescent host)

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 to form a hole injection layer with a thickness of 60 nm. Then, N,N'-Bis(1-naphthalenyl)-N,N'-bis-phenyl-(1,1'-biphenyl)-4,4'-diamine (hereinafter abbreviated as NPB) was formed. A hole transport layer was formed by vacuum deposition to a thickness of 60 nm.

Next, a 30 nm thick light-emitting layer was formed on the hole transport layer, and the compound P-1 of the present invention was used as a host, and tris(2-phenylpyridine)-iridium (hereinafter abbreviated as Ir(ppy) ₃ ) was used as a dopant. , Host and dopant were used in a weight ratio of 95:5.

Next, (1,1'-bisphenyl)-4-oleito)bis(2-methyl-8-quinolinoleito)aluminum (hereinafter abbreviated as BAlq) on the light emitting layer was vacuum deposited to a thickness of 10 nm. A hole blocking layer was formed, and tris(8-quinolinol)aluminum (hereinafter abbreviated as Alq ₃ ) was deposited thereon to a thickness of 40 nm to form an electron transport layer. Subsequently, an organic electroluminescent device was manufactured by depositing LiF on the electron transport layer to a thickness of 0.2 nm to form an electron injection layer, and then depositing Al to a thickness of 150 nm to form a cathode.

[Example 2] to [Example 21]

An organic electroluminescent device was manufactured in the same manner as in Example 1, except that the compound of the present invention shown in Table 4 below was used instead of the compound P-1 as the host material of the light emitting layer.

[ Comparative example 1] to [ Comparative example 3]

An organic electroluminescent device was manufactured in the same manner as in Example 1, except that one of the following Comparative Compounds 1 to 3 was used instead of Compound P-1 of the present invention as the host material of the light emitting layer.

<Comparative compound 1> <Comparative compound 2> <Comparative compound 3>

Electroluminescence (EL) characteristics were measured by PR-650 of photoresearch by applying a net bias DC voltage to the organic electroluminescent devices manufactured by Examples 1 to 27 and Comparative Examples 1 to 3 of the present invention. , T95 lifespan was measured using a life measurement equipment from Max Science at a standard luminance of 5000 cd/m ² . The measurement results are shown in Table 4 below.

[Table 4]

As can be seen from the results of Table 4, when using the compound according to an embodiment of the present invention as a green phosphorescent host material of the light emitting layer, the electrical properties of the device were significantly improved compared to Comparative Compounds 1 to 3.

When comparing Comparative Examples 1 to 3, device characteristics were better when Comparative Compound 2 or Comparative Compound 3 having a condensed heteroaromatic ring was used as a host material, rather than CBP (Comparative Compound 1) commonly used as a host material.

In addition, the compound represented by Formulas 4 to 9 of the present invention having a skeleton similar to that of Comparative Compound 3 but having a fused indol to benzoquinazoline as a host is used as a host or indole to Comparative Compound 3 and benzoquinazoline. The condensed direction is the same, but when one or more benzene rings are condensed, the driving voltage, efficiency, and lifespan are higher than those of Comparative Compound 3 when the compounds represented by Chemical Formulas 10 to 15 of the present invention containing at least six rings are used as hosts. All improved further.

It has hole characteristics, light efficiency characteristics, energy levels (LUMO, HOMO levels, T1 levels), hole injection and hole injection & mobility characteristics depending on the fusion location of the ring or the number of rings constituting the core, even if the core is a similar compound. This is because the properties of compounds such as electron blocking ability are different.

[ Example 28] to [ Example 38] Red Organic light emitting device( Red Phosphorescent host)

An organic electroluminescent device was manufactured in the same manner as in Example 1, except that the compound of Table 5 as a host was used as a dopant, bis-(1-phenylisoquinolyl) iridium(III)acetylacetonat.

[ Comparative example 4] to [ Comparative example 6]

An organic electroluminescent device was manufactured in the same manner as in Example 1, except that one of the comparative compounds 1 to 3 was used as a host and bis-(1-phenylisoquinolyl) iridium(III)acetylacetonat was used as a dopant. .

The electroluminescence (EL) characteristics of the organic electroluminescent devices of Examples 28 to 38 and Comparative Examples 4 to 6 manufactured as described above were measured by using a photoresearch PR-650 by applying a direct bias DC voltage. Results T95 life was measured using a life measurement equipment manufactured by Max Science at a reference luminance of 2500 cd/m ² . The following table shows the results of device fabrication and evaluation.

[Table 5]

From Table 5, it can be seen that even in the case of the red organic light emitting device, when the compound of the present invention is used as the phosphorescent host material rather than Comparative Compounds 1 or 2, the driving voltage, efficiency, and lifespan are significantly improved.

In addition, comparing Example 32 and Example 35, it can be seen that in Example 35, the driving voltage, efficiency, and lifetime are all better. Compounds P-102 and P-165 used in the above two examples are similar in that triazine is bonded to N of carbazole, but in Formula 1, which of R ² to R ⁴ forms a ring is different. In the case of a red organic light emitting device, when using a compound in which R ² forms a ring (Example 35) rather than a compound in which R ³ or R ⁴ forms a ring in Example 1 (Example 32), the driving voltage, efficiency, and lifetime It can be seen that all of these are improved. This is also the case for Examples 29 and 38 in which quinazoline is bound to N of carbazole.

However, referring to Table 4, in the case of the green organic light-emitting device, the driving voltage when the compound having R ³ or R ⁴ as a ring is used as a host than when the compound having R ² as a ring as a host in Formula 1 is used as a host. , It can be seen that the efficiency and life are further improved. In Table 4, both Compound P-37 used in Example 8 and Compound P-165 used in Example 18 are similar in that triazine is bonded to N of carbazole, but R ² forms a ring (Compound P -165) Or it is different whether R ⁴ has formed a ring (Compound P-37).

Therefore, in Formula 1, a compound in which R ² forms a ring is more suitable as a phosphorescent host of a red organic light emitting device, and a compound in which R ³ or R ⁴ is formed as a ring is more suitable as a phosphorescent host of a green organic light emitting device. Able to know.

These results show that hole properties, light efficiency properties, energy levels (LUMO, HOMO levels, T1 levels), hole injection properties, hole injection properties, and electron blocking abilities, depending on the location of benzene fusion, even if the core is a similar compound. blocking), etc., suggests that the properties of the compound may be changed and the device characteristics may be changed.

The above description is merely illustrative of the present invention, and those skilled in the art belonging to the present invention can improve performance by including other compounds in the light emitting layer without departing from the essential characteristics of the present invention. Various modifications will be possible. Therefore, the embodiments disclosed herein are not intended to limit the present invention, but to explain 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 technologies within the equivalent range should be interpreted as being included in the scope of the present invention.

100: organic electrical 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 (12)

Compound represented by the formula (1):
<Formula 1>

In Chemical Formula 1,
X and Y are independently of each other N-(L-Ar),
n and m are each 0 or 1, n+m is an integer of 1 or more,
R ¹ to R ⁴ are independently of each other hydrogen; heavy hydrogen; halogen; Cyano group; 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; C ₃ ~ C ₆₀ aliphatic 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 ₃₀ Aryloxy group; And -L'-N(R _a )(R _b ); is selected from the group consisting of, adjacent R ² , neighboring R ³ , neighboring R ⁴ , R ¹ and R ³ , R ² and R ³ , or R ³ and R ⁴ may be bonded to each other to form a ring,
When m is 1, adjacent R ² , adjacent R ⁴ , R ¹ and R ³ , R ² and R ³ , or R ³ and R ⁴ are bonded to each other to form a ring,
a is an integer from 0 to 2, b is an integer from 0 to 3, c is an integer from 0 to 2, d is an integer from 0 to 2, and each of them is an integer of 2 or more, each of a plurality of R ¹ and a plurality of R ² Each of each of the plurality of R ^3, each of the plurality of R ⁴ is the same as or different from each other,
L and L'are each independently a single bond; C ₆ ~ C ₆₀ Arylene group; Fluorylene group; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; And C ₃ ~ C _{60 It} is selected from the group consisting of an aliphatic ring,
Ar is 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; C ₃ ~ C ₆₀ aliphatic 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 ₃₀ Aryloxy group; C ₆ ~ C ₃₀ Arylthio group; And combinations thereof,
R _a and R _b are independently of each other 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; C ₃ ~ C ₆₀ aliphatic ring group; And combinations thereof. According to claim 1,
Chemical Formula 1 is a compound characterized in that represented by the following Chemical Formula 2 or Chemical Formula 3:
<Formula 2><Formula3>

In the above formula, R ¹ ~R ⁴ , L, Ar are as defined in claim 1. According to claim 1,
Formula 1 is a compound characterized in that represented by one of the following formulas 4 to 15:
<Formula 4><Formula5><Formula6>

<Formula 7><Formula8><Formula9>

<Formula 10><Formula11><Formula12>

<Formula 13><Formula14><Formula15>

In the above formula, L and Ar are as defined in claim 1. According to claim 1,
The Ar is a compound represented by the following formula Ar-1 or formula Ar-2:
<Formula Ar-1><FormulaAr-2>

In the above formula, Q ¹ ~ Q ⁹ are independently of each other N or C (R ^c ),
The Z ring is selected from the group consisting of the following Z-1 to Z-15,
<Formula Z-1><FormulaZ-2><FormulaZ-3><FormulaZ-4>

<Formula Z-5><FormulaZ-6><FormulaZ-7><FormulaZ-8>

<Formula Z-9><FormulaZ-10><FormulaZ-11><FormulaZ-12>

<Formula Z-13><FormulaZ-14><FormulaZ-15>

W ¹ and W ² are independently of each other N-(L ¹ -Ar ¹ ), S, O or C(R')(R"),
V is independently of each other N or C(R ^d ), and each V is the same or different from each other,
L ¹ is a single bond; C ₆ ~ C ₆₀ Arylene group; Fluorylene group; C ₂ ~ C ₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P; And C ₃ ~ C _{60 It} is selected from the group consisting of an aliphatic ring,
Ar ¹ is 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; C ₃ ~ C ₆₀ aliphatic 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 ₃₀ Aryloxy group; C ₆ ~ C ₃₀ Arylthio group; And combinations thereof,
The R ^c , R ^d , R'and R" are independently deuterium; halogen; a silane group unsubstituted or substituted with a C ₁ -C ₂₀ alkyl group or a C ₆ -C ₂₀ aryl group; a siloxane group; a boron group; germanium group; an aryl group substituted or unsubstituted phosphine oxide of a C ₁ -C ₂₀ alkyl or C ₆ -C ₂₀ of; cyano group; nitro group; an alkylthio import of C ₁ -C _20; a C ₁ -C ₂₀ Alkoxy group; C ₆ -C ₂₀ arylalkoxy group; C ₁ -C ₂₀ alkyl group; C ₂ -C ₂₀ alkenyl group; C ₂ -C ₂₀ alkynyl group; C ₆ -C ₂₀ aryl group; fluorene Diary; C ₂ -C ₂₀ heterocyclic group containing at least one hetero atom selected from the group consisting of O, N, S, Si and P; C ₃ -C ₂₀ aliphatic ring group; C ₇ -C ₂₀ Arylalkyl group; and C ₈ -C ₂₀ arylalkenyl group, and adjacent R ^c or neighboring R ^d may combine with each other to form a ring, and R'and R" are bonded to each other. Can form a ring. According to claim 1,
The compound represented by Formula 1 is one of the following compounds:

. In the organic electric device including a first electrode, a second electrode, and an organic material layer formed between the first electrode and the second electrode,
The organic material layer is characterized in that it comprises a single compound or two or more compounds represented by the formula (1) of claim 1. The method of claim 6,
The organic material layer comprises 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. The method of claim 7,
The compound is an organic electrical device, characterized in that included in the light emitting layer. The method of claim 8,
The compound represented by Chemical Formula 1 is used as a red host of the light emitting layer, and R ² in Chemical Formula 1 forms an ring. The method of claim 8,
The compound represented by Chemical Formula 1 is used as a green host of the light emitting layer, and R ³ or R ⁴ in Chemical Formula 1 forms a ring. A display device comprising the organic electroluminescent element of claim 6; And
An electronic device comprising; a control unit for driving the display device. The method of claim 11,
The organic electric device is an electronic device, characterized in that selected from the group consisting of an organic electroluminescent device, an organic solar cell, an organic photoreceptor, an organic transistor, a monochromatic lighting device and a quantum dot display device.

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