KR102634284B1 - Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof - Google Patents

Abstract

The present invention provides a novel compound that can improve the luminous efficiency, stability, and lifespan of the device, an organic electric device using the same, and an electronic device thereof.

Description

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

The present invention relates to compounds for organic electric devices, organic electric devices using the same, and electronic devices thereof.

In general, organic luminescence refers to a phenomenon that converts electrical energy into light energy using organic materials. Organic electric devices that utilize the organic light emission phenomenon usually have a structure including an anode, a cathode, and an organic material layer between them. Here, the organic material layer is often composed of a multi-layer structure made of different materials to increase the efficiency and stability of the organic electric device, and may be composed 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 organic layers in organic electric devices can 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 materials can be classified into high-molecular and low-molecular types depending on their molecular weight, and can be classified into fluorescent materials derived from the singlet excited state of electrons and phosphorescent materials derived from the triplet excited state of electrons depending on the light-emitting mechanism. there is. In addition, light-emitting materials can be divided into blue, green, and red light-emitting materials depending on the color of the light, and yellow and orange light-emitting materials necessary to realize better natural colors.

On the other hand, when only one substance is used as a light-emitting material, the maximum emission wavelength moves to a longer wavelength due to intermolecular interactions, and problems arise such as a decrease in color purity or a decrease in the efficiency of the device due to the emission attenuation effect, thereby increasing color purity and energy transfer. In order to increase luminous efficiency through , a host/dopant system can be used as a luminescent material. The principle is that when a small amount of a dopant with a smaller energy band gap than the host forming the light-emitting layer is mixed into the light-emitting layer, excitons generated in the light-emitting layer are transported to the dopant, producing highly efficient light. At this time, since the wavelength of the host moves to the wavelength of the dopant, light of the desired wavelength can be obtained depending on the type of dopant used.

Currently, the portable display market is increasing in size toward large-area displays, which requires greater power consumption than that required for existing portable displays. Therefore, power consumption has become a very important factor for portable displays that have a limited power source such as batteries, and issues of efficiency and lifespan must also be resolved.

Efficiency, lifespan, and driving voltage are related to each other. As efficiency increases, the driving voltage relatively decreases. As the driving voltage decreases, crystallization of organic substances due to Joule heating generated during driving decreases, resulting in less crystallization of organic substances. Life expectancy tends to increase. However, efficiency cannot be maximized simply by improving the organic layer. This is because long lifespan and high efficiency can be achieved at the same time when the energy level and T1 value between each organic material layer and the intrinsic properties of the material (mobility, interface properties, etc.) are optimally combined.

Therefore, it must have stable characteristics against Joule heating generated during device operation while delaying the penetration and diffusion of metal oxides from the anode electrode (ITO) into the organic layer, which is one of the causes of shortened lifespan of organic electric devices. , OLED devices are mainly formed by deposition methods, and there is a need to develop materials that can withstand deposition for a long time, that is, materials with strong heat resistance properties.

In other words, in order to fully demonstrate the excellent characteristics of organic electric devices, the materials that make up the organic layer within the device, such as hole injection materials, hole transport materials, light-emitting materials, electron transport materials, and electron injection materials, must be supported by stable and efficient materials. This should take precedence, but the development of stable and efficient organic material layer materials for organic electric devices has not yet been sufficiently developed. Therefore, the development of new materials continues to be required, and in particular, the development of host materials for the light-emitting layer is urgently required.

In order to solve the problems of the above-mentioned background technology, the present invention has discovered a compound with a novel structure, and the fact that when this compound is applied to an organic electric device, the luminous efficiency, stability, and lifespan of the device can be greatly improved. revealed.

Accordingly, the purpose of the present invention is to provide a novel compound, an organic electric device using the same, and an electronic device thereof.

The present invention provides a compound represented by the following formula 1-1.

<Formula 1-1>

In another aspect, the present invention provides an organic electric device and an electronic device thereof including the compound represented by Formula 1-1.

By using the compound according to the present invention, high luminous efficiency, low driving voltage, and high heat resistance of the device can be achieved, and the color purity and lifespan of the device can be greatly improved.

1 to 3 are exemplary diagrams of organic electroluminescent devices according to the present invention.

Hereinafter, the present invention will be described in detail with reference to embodiments. In describing the present invention, if it is determined that a detailed description of a related known configuration or function may obscure the gist of the present invention, the detailed description will be omitted.

Additionally, when describing the components of the present invention, terms such as first, second, A, B, (a), and (b) may be used. These terms are only used to distinguish the component from other components, and the nature, sequence, or order of the component is not limited by the term. When a component is described as being “connected,” “coupled,” or “connected” to another component, that component may be directly connected or connected to that other component, but there is another component between each component. It will be understood that elements may be “connected,” “combined,” or “connected.”

As used in this specification and the appended claims, unless otherwise noted, the following terms have the following meanings:

As used herein, the term “halo” or “halogen” refers to fluorine (F), bromine (Br), chlorine (Cl), or iodine (I), unless otherwise specified.

As used in the present invention, the term "alkyl" or "alkyl group", unless otherwise specified, has a single bond of 1 to 60 carbon atoms, and includes straight chain alkyl group, branched chain alkyl group, cycloalkyl (cycloaliphatic) group, and alkyl-substituted cyclo. It refers to radicals of saturated aliphatic functional groups, including alkyl groups and cycloalkyl-substituted alkyl groups.

As used in the present invention, the terms "alkenyl group", "alkenyl group" or "alkynyl group", unless otherwise specified, each have a double or triple bond of 2 to 60 carbon atoms, and include a straight or branched chain group. , but is not limited to this.

The term “cycloalkyl” used in the present invention refers to alkyl forming a ring having 3 to 60 carbon atoms, unless otherwise specified, but is not limited thereto.

As used in the present invention, the term "alkoxyl group", "alkoxy group", or "alkyloxy group" refers to an alkyl group to which an oxygen radical is attached, and has a carbon number of 1 to 60, and is limited thereto, unless otherwise specified. That is not the case.

The term “aryloxyl group” or “aryloxy group” used in the present invention refers to an aryl group to which an oxygen radical is attached, and has 6 to 60 carbon atoms unless otherwise specified, but is not limited thereto.

The terms “aryl group” and “arylene group” used in the present invention each have 6 to 60 carbon atoms unless otherwise specified, and are not limited thereto. In the present invention, an aryl group or arylene group refers to an aromatic group of a single ring or multiple rings, and includes an aromatic ring formed by combining adjacent substituents or participating in a reaction. For example, the aryl group may be a phenyl group, biphenyl group, fluorene group, or spirofluorene group.

The prefix “aryl” or “ar” refers to a radical substituted with an aryl group. For example, an arylalkyl group is an alkyl group substituted with an aryl group, an arylalkenyl group is an alkenyl group substituted with an aryl group, and a radical substituted with an aryl group has the carbon number described in this specification.

Additionally, when prefixes are named consecutively, it means that the substituents are listed in the order they are listed first. For example, an arylalkoxy group refers to an alkoxy group substituted with an aryl group, an alkoxylcarbonyl group refers to a carbonyl group substituted with an alkoxyl group, and an arylcarbonylalkenyl group refers to an alkenyl group substituted with an arylcarbonyl group. And here, the arylcarbonyl group is a carbonyl group substituted with an aryl group.

The term "heterocyclic group" used in the present invention, unless otherwise specified, contains one or more heteroatoms, has a carbon number of 2 to 60, includes at least one of a single ring and a multiple ring, and includes a heteroaliphatic ring and a heterocyclic group. Contains an aromatic ring. It may also be formed by combining neighboring functional groups.

As used herein, the term “heteroatom” refers to N, O, S, P or Si, unless otherwise specified.

Additionally, the “heterocyclic group” may also include a ring containing SO ₂ instead of carbon forming the ring. For example, “heterocyclic group” includes the following compounds:

As used in the present invention, the term "fluorenyl group" or "fluorenylene group" refers to a monovalent or divalent functional group in which R, R' and R" are all hydrogen in the following structure, respectively, unless otherwise specified. 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 and the carbon to which they are bonded This includes cases where they form a spiro compound together.

The term "spiro compound" used in the present invention has a 'spiro union', and the spiro union refers to a connection made by two rings sharing only one atom. At this time, the atom shared between the two rings is called a 'spiro atom', and depending on the number of spiro atoms in one compound, they are 'monospiro-', 'dispiro-', and 'trispiro-' respectively. 'It is called a compound.

Unless otherwise specified, the term "aliphatic" used in the present invention refers to an aliphatic hydrocarbon having 1 to 60 carbon atoms, and the term "aliphatic ring" refers to an aliphatic hydrocarbon ring having 3 to 60 carbon atoms.

Unless otherwise specified, the term "ring" used in the present invention refers to an aliphatic ring having 3 to 60 carbon atoms, an aromatic ring having 6 to 60 carbon atoms, a heterocycle having 2 to 60 carbon atoms, or a fused ring consisting of a combination thereof, Contains saturated or unsaturated rings.

Other heterocompounds or heteroradicals other than the above-described heterocompounds include one or more heteroatoms, but are not limited thereto.

Also, unless explicitly stated otherwise, in the term “substituted or unsubstituted” used in the present invention, “substituted” refers to deuterium, halogen, amino group, nitrile group, nitro group, C ₁ to C ₂₀ alkyl group, C ₁ to C ₂₀ alkoxyl 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 group, C ₃ ~ C ₂₀ cycloalkyl group, C ₆ ~ C ₂₀ aryl group, C ₆ ~ C ₂₀ aryl group substituted with deuterium, C ₈ ~ C ₂₀ arylalkenyl group, silane group, boron group, germanium group, and C ₂ to C ₂₀ heterocyclic group, but is not limited to these substituents.

Additionally, unless explicitly stated otherwise, the chemical formula used in the present invention is applied identically to the substituent definition by the index definition in the following chemical formula.

Here, when a is an integer of 0, the substituent R ¹ is absent, and when a is an integer of 1, one substituent R ¹ is bonded to any one of the carbons forming the benzene ring, and when a is an integer of 2 or 3, Each is bonded as follows, where R ¹ may be the same or different from each other, and when a is an integer of 4 to 6, it is bonded to the carbon of the benzene ring in a similar manner, while indicating the hydrogen bonded to the carbon forming the benzene ring. is omitted.

Hereinafter, a compound according to one aspect of the present invention and an organic electric device containing the same will be described.

The present invention provides a compound represented by the following formula 1-1.

<Formula 1-1>

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

1) L ¹ is a substituent represented by any of the following formulas L-1 to L-4,

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

2) L ² is a single bond; or an arylene group of C ₆ to C ₆₀ ;

3) Ar is a C ₆ to C ₆₀ aryl group, preferably a C ₆ to C ₃₀ aryl group, more preferably a C ₆ to C ₂₄ aryl group, such as phenylene, biphenyl, naphthalene, tert. It may be phenyl, etc.,

4) Ring A has the following formula (a); or a substituent represented by formula b;

<Formula a> <Formula b>

5) R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ⁶ are each the same or different and, independently of each other, hydrogen; or deuterium;

6) R ⁷ is hydrogen; heavy hydrogen; Aryl group of C ₆ to C ₆₀ ; and an aryl group of C ₆ to C ₆₀ substituted with deuterium;

7) a and d are independently integers from 0 to 5, b and f are independently integers from 0 to 6, c, e, g and h are independently integers from 0 to 4, and i is It is an integer from 0 to 7,

8) The * above refers to the binding position,

9) Here, the aryl group and the arylene group are each hydrogen; C ₆ ~ C ₂₀ aryl group; and a C ₆ to C ₂₀ aryl group substituted with deuterium; and may be further substituted with one or more substituents selected from the group consisting of deuterium and deuterium when forming a benzene ring between R ⁴ ; C ₆ ~ C ₂₀ aryl group; and a C ₆ to C ₂₀ aryl group substituted with deuterium; and may be further substituted with one or more substituents selected from the group consisting of.

The L ² may be represented by any one of the following formulas (a-1) to (a-20).

<Formula a-1> <Formula a-2> <Formula a-3> <Formula a-4> <Formula a-5>

<Formula a-6> <Formula a-7> <Formula a-8> <Formula a-9> <Formula a-10>

<Formula a-11> <Formula a-12> <Formula a-13> <Formula a-14> <Formula a-15>

<Formula a-16> <Formula a-17> <Formula a-18> <Formula a-19> <Formula a-20>

In the above formulas (a-1) to (a-20), each symbol may be defined as follows.

1) R ¹⁰¹ and R ¹⁰² are the same or different and are independently hydrogen; heavy hydrogen; C ₆ ~ C ₂₀ aryl group; Or an aryl group of C ₆ to C ₂₀ substituted with deuterium;

When R ¹⁰¹ and R ¹⁰² are aryl groups, they may be phenylene, biphenyl, naphthalene, terphenyl, etc.,

2) aa, ab and ac are independently integers from 0 to 4, ad is an integer from 0 to 6, and ae is an integer from 0 to 8,

3) * means the position where triazine or Ar is bonded.

The Ar may be represented by any one of the following formulas (b-1) to (b-8).

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

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

In Formulas b-1 to b-8, each symbol may be defined as follows.

1) R ¹⁰³ is hydrogen; heavy hydrogen; C ₆ ~ C ₂₀ aryl group; Or an aryl group of C ₆ to C ₂₀ substituted with deuterium;

If R ¹⁰³ is an aryl group, it may be phenylene, biphenyl, naphthalene, terphenyl, etc.,

2) ba is an integer from 0 to 5, bb is an integer from 0 to 7, bc is an integer from 0 to 9,

3) means the position that combines with L.

The formula L-1 may preferably be represented by any one of the following formulas L-1-1 to formula L-1-3.

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

{In Formula L-1-1 to Formula L-1-3, R ⁵ , e and * are as defined above.}

The formula L-2 may preferably be represented by any one of the following formulas L-2-1 to L-2-4.

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

{In Formula L-2-1 to Formula L-2-4, R ⁵ , f and * are as defined above.}

The formula L-3 may preferably be represented by any one of the following formulas L-3-1 to L-3-8.

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

<Formula L-3-5> <Formula L-3-6> <Formula L-3-7> <Formula L-3-8>

{In Formula L-3-1 to Formula L-3-8, R ⁵ , f and * are as defined above.}

The formula L-4 may preferably be represented by any one of the following formulas L-4-1 to L-4-6.

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

<Formula L-4-4> <Formula L-4-5> <Formula L-4-6>

{In the above formulas L-4-1 to L-4-6, R ⁵ , R ⁶ , g, h and * are as defined above.}

Additionally, the present invention provides a compound where Formula 1-1 is represented by Formula 1-1-a or Formula 1-1-b.

<Formula 1-1-a> <Formula 1-1-b>

{In Formula 1-1-a or Formula 1-1-b, R ¹ , R ² , R ³ , R ⁴ , R ⁷ , L ¹ , L ² , Ar, a, b, c, d and i are Same as defined above.}

Additionally, the present invention provides a compound where Formula 1-1 is represented by any one of the following Formulas 1-1-1 to 1-1-5.

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

<Formula 1-1-3> <Formula 1-1-4>

<Formula 1-1-5>

{In Formulas 1-1-1 to 1-1-5, R ^{1 ,} R ² , R ^{3 , R 4} , R ⁵ , R ⁶ , R ⁷ , L ² , Ar, a, b, c, d , e, f, g, h and i are the same as defined above.}

Additionally, the present invention provides a compound in which Formula 1-1 is represented by any of the following Formulas 1-1-1-a to 1-1-1-c.

<Formula 1-1-1-a> <Formula 1-1-1-b>

<Formula 1-1-1-c>

{In Formula 1-1-1-a to Formula 1-1-1-c, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , L ² , Ar, a, b, c, d and e is as defined above.}

Additionally, the present invention provides a compound in which Formula 1-1 is represented by any of the following Formulas 1-1-2-a to 1-1-2-c.

<Formula 1-1-2-a> <Formula 1-1-2-b>

<Formula 1-1-2-c>

{In Formula 1-1-2-a to Formula 1-1-2-c, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , L ² , Ar, a, b, c, d and f is as defined above.}

Additionally, the present invention provides a compound where Formula 1-1 is represented by the following Formula 1-1-3-a or Formula 1-1-3-b.

<Formula 1-1-3-a> <Formula 1-1-3-b>

{In Formula 1-1-3-a or Formula 1-1-3-b, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , L ² , Ar, a, b, c, d and f is as defined above.}

Additionally, the present invention provides a compound where Formula 1-1 is represented by the following Formula 1-1-4-a.

<Formula 1-1-4-a>

{In the above formula 1-1-4-a, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , L ² , Ar, a, b, c, d, g and h are defined above It is the same as what happened.}

Additionally, the present invention provides a compound where Formula 1-1 is represented by the following Formula 1-1-4-b or Formula 1-1-4-c.

<Formula 1-1-4-b> <Formula 1-1-4-c>

{In Formula 1-1-4-b or Formula 1-1-4-c, R ¹ , R ² , R ³ , R 4 , R ⁵ , ^{R 6 ,} L ² , Ar, a, b, c, d, g and h are as defined above.}

Additionally, the present invention provides a compound in which Formula 1-1 is represented by any of the following Formulas 1-1-5-a to 1-1-5-c.

<Formula 1-1-5-a> <Formula 1-1-5-b>

<Formula 1-1-5-c>

{In Formula 1-1-5-a to Formula 1-1-5-c, R ¹ , R ² , R ³ , R ⁵ , R ⁷ , L ² , Ar, a, b, c, e and i is as defined above.}

Additionally, the present invention provides a compound represented by Formula 1-1, wherein the compound is represented by any one of the following compounds P-1 to P-44.

Referring to FIG. 1, the organic electric device 100 according to the present invention has a first electrode 110, a second electrode 170, and a chemical formula between the first electrode 110 and the second electrode 170. It is provided with an organic material layer containing a single compound or two or more compounds represented by 1). At this time, the first electrode 110 may be an anode or an anode, and the second electrode 170 may be a cathode or a cathode. In the case of the inverted type, the first electrode may be a cathode and the second electrode may be an anode.

The organic material layer may sequentially include a hole injection layer 120, a hole transport layer 130, a light emitting layer 140, an electron transport layer 150, and an electron injection layer 160 on the first electrode 110. At this time, the remaining layers except for the light emitting layer 140 may not be formed. It may further include a hole blocking layer, an electron blocking layer, a light emission auxiliary layer 220, a buffer layer 210, etc., and an electron transport layer 150, etc. may serve as a hole blocking layer. (see Figure 2)

Additionally, the organic electric device according to an embodiment of the present invention may further include a protective layer or a light efficiency improvement layer 180. This light efficiency improvement layer may be formed on a side of both sides of the first electrode that is not in contact with the organic material layer, or on both sides of the second electrode that is not in contact with the organic material layer. The compound according to an embodiment of the present invention applied to the organic layer is a hole injection layer 120, a hole transport layer 130, a light emitting auxiliary layer 220, an electron transport auxiliary layer, an electron transport layer 150, an electron injection layer ( 160), it may be used as a host or dopant of the light emitting layer 140, a hole blocking layer, or a material for improving light efficiency. Preferably, for example, a compound according to formula (1) of the present invention can be used as a material for the light-emitting layer.

The organic material layer may include two or more stacks including a hole transport layer, a light-emitting layer, and an electron transport layer sequentially formed on the anode, and may further include a charge generation layer formed between the two or more stacks. (see Figure 3)

Meanwhile, even if it is the same core, the band gap, electrical properties, and interface properties may vary depending on which substituent is attached to which position, so the selection of the core and the combination of sub-substituents attached to it are very important. It is important, and in particular, when the energy level and T1 value between each organic layer and the intrinsic properties of the material (mobility, interface properties, etc.) are optimally combined, long lifespan and high efficiency can be achieved at the same time.

An organic electroluminescent device according to an embodiment of the present invention may be manufactured using a physical vapor deposition (PVD) method. For example, an anode is formed by depositing a metal or a conductive metal oxide or an alloy thereof on a substrate, and a hole injection layer 120, a hole transport layer 130, a light emitting layer 140, an electron transport layer 150, and It can be manufactured by forming an organic material layer including the electron injection layer 160 and then depositing a material that can be used as a cathode on it.

In addition, in the present invention, the organic layer is formed by any one of a spin coating process, nozzle printing process, inkjet printing process, slot coating process, dip coating process, and roll-to-roll process, and the organic layer contains the compound as an electron transport material. Provided is an organic electric device characterized in that:

As another specific example, the present invention provides an organic electric device characterized in that the same type or different compounds of the compound represented by the formula (1) are mixed and used in the organic material layer.

In addition, the present invention provides a light-emitting layer composition containing the compound represented by the formula (1), and provides an organic electric device containing the light-emitting layer.

In addition, the present invention provides a display device including the above-described organic electric device; and a control unit that drives the display device.

In another aspect, the present invention provides an electronic device wherein the organic electric device is at least one of an organic electroluminescent device, an organic solar cell, an organic photoreceptor, an organic transistor, and a monochromatic or white lighting device. At this time, the electronic device may be a current or future wired or wireless communication terminal, and includes all electronic devices such as mobile communication terminals such as mobile phones, PDAs, electronic dictionaries, PMPs, remote controls, navigation devices, game consoles, various TVs, and various computers.

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

[Synthesis example]

The compound (final products) represented by Chemical Formula 1-1 according to the present invention is synthesized by reacting Sub 1 and Sub 2 as shown in Scheme 1 below, but is not limited thereto.

<Scheme 1>

I. Synthesis of Sub1

Compounds belonging to Sub1 may be, but are not limited to, the following compounds, and Table 1 below shows the FD-MS (Field Desorption-Mass Spectrometry) values of the compounds belonging to Sub1.

compound FD-MS compound FD-MS Sub1-1 m/z=280.16(C ₁₈ H ₂₁ BO ₂ =280.17) Sub1-2 m/z=280.16(C ₁₈ H ₂₁ BO ₂ =280.17) Sub1-3 m/z=285.19(C ₁₈ H ₁₆ D ₅ BO ₂ =285.2) Sub1-4 m/z=280.16(C ₁₈ H ₂₁ BO ₂ =280.17) Sub1-5 m/z=330.18(C ₂₂ H ₂₃ BO ₂ =330.23) Sub1-6 m/z=330.18(C ₂₂ H ₂₃ BO ₂ =330.23) Sub1-7 m/z=330.18(C ₂₂ H ₂₃ BO ₂ =330.23) Sub1-8 m/z=330.18(C ₂₂ H ₂₃ BO ₂ =330.23) Sub1-9 m/z=335.21(C ₂₂ H ₁₈ D ₅ BO ₂ =335.26) Sub1-10 m/z=330.18(C ₂₂ H ₂₃ BO ₂ =330.23) Sub1-11 m/z=335.21(C ₂₂ H ₁₈ D ₅ BO ₂ =335.26) Sub1-12 m/z=356.19(C ₂₄ H ₂₅ BO ₂ =356.27) Sub1-13 m/z=360.22(C ₂₄ H ₂₁ D ₄ BO ₂ =360.3) Sub1-14 m/z=356.19(C ₂₄ H ₂₅ BO ₂ =356.27) Sub1-15 m/z=330.18(C ₂₂ H ₂₃ BO ₂ =330.23) Sub1-16 m/z=330.18(C ₂₂ H ₂₃ BO ₂ =330.23) Sub1-17 m/z=330.18(C ₂₂ H ₂₃ BO ₂ =330.23) Sub1-18 m/z=334.2(C ₂₂ H ₁₉ D ₄ BO ₂ =334.26) Sub1-19 m/z=406.21(C ₂₈ H ₂₇ BO ₂ =406.33) Sub1-20 m/z=410.24(C ₂₈ H ₂₃ D ₄ BO ₂ =410.36) Sub1-21 m/z=410.24(C ₂₈ H ₂₃ D ₄ BO ₂ =410.36) Sub1-22 m/z=406.21(C ₂₈ H ₂₇ BO ₂ =406.33) Sub1-23 m/z=409.23(C ₂₈ H ₂₄ D ₃ BO ₂ =409.35) Sub1-24 m/z=406.21(C ₂₈ H ₂₇ BO ₂ =406.33) Sub1-25 m/z=410.24(C ₂₈ H ₂₃ D ₄ BO ₂ =410.36)

II. Synthesis of Sub2

Sub2 of Scheme 1 is synthesized through the reaction route of Scheme 2 below, but is not limited thereto.

<Scheme 2>

1. Sub2-1 synthesis example

Sus2b-1 (13.9 g, 61.5 mmol) was dissolved in THF (Tetrahydrofuran) (310 mL) in a round bottom flask, followed by Sub2a-1 (25.0 g, 61.5 mmol), NaOH (7.4 g, 184.6 mmol), and Pd(PPh). ₃ ) ₄ (4.27 g, 3.69 mmol) and water (155 mL) were added and stirred at 80°C. When the reaction was completed, the extract was extracted with CH ₂ Cl ₂ and water, and the organic layer was dried over MgSO ₄ and concentrated. Afterwards, the produced compound was recrystallized by applying a silica gel column to obtain 21.5 g of product (yield 74.5%).

2. Sub2-2 synthesis example

(1) Sub2a-2 synthesis example

After dissolving Sub2d-2 (22.9 g, 69.4 mmol) in THF (350 mL) in a round bottom flask, Sub2c-1 (20.0 g, 69.4 mmol), NaOH (8.3 g, 208.2 mmol), Pd(PPh ₃ ) ₄ (4.81 g, 4.16 mmol) and water (175 mL) were added, and 20.4 g of product (yield 71.4%) was obtained using the above synthesis method of Sub2-1.

(2) Sub2-2 synthesis example

After dissolving Sub2b-1 (11.2 g, 49.5 mmol) in THF (250 mL) in a round bottom flask, Sub2a-2 (20.4 g, 49.5 mmol), NaOH (5.9 g, 148.6 mmol), Pd(PPh ₃ ) ₄ (3.44 g, 2.97 mmol) and water (125 mL) were added, and 16.9 g of product (yield 71.7%) was obtained using the above synthesis method of Sub2-1.

3. Sub2-9 synthesis example

After dissolving Sub2b-9 (13.0 g, 36.9 mmol) in THF (185 mL) in a round bottom flask, Sub2a-1 (15.0 g, 36.9 mmol), NaOH (4.4 g, 110.7 mmol), Pd(PPh ₃ ) ₄ (2.56 g, 2.21 mmol) and water (92 mL) were added, and 16.1 g of product (yield 73.3%) was obtained using the above synthesis method of Sub2-1.

4. Sub2-13 synthesis example

After dissolving Sub2b-13 (13.0 g, 36.9 mmol) in THF (185 mL) in a round bottom flask, Sub2a-1 (15.0 g, 36.9 mmol), NaOH (4.4 g, 110.7 mmol), Pd(PPh ₃ ) ₄ (2.56 g, 2.21 mmol) and water (92 mL) were added, and 16.0 g of product (yield 72.7%) was obtained using the above synthesis method of Sub2-1.

Compounds belonging to Sub2 may be, but are not limited to, the following compounds, and Table 2 below shows the FD-MS (Field Desorption-Mass Spectrometry) values of the compounds belonging to Sub2.

compound FD-MS compound FD-MS Sub2-1 m/z=469.13(C ₃₁ H ₂₀ ClN ₃ =469.97) Sub2-2 m/z=474.17(C ₃₁ H ₁₅ D ₅ ClN ₃ =475.00) Sub2-3 m/z=472.15(C ₃₁ H ₁₇ D ₃ ClN ₃ =472.99) Sub2-4 m/z=474.17(C ₃₁ H ₁₅ D ₅ ClN ₃ =475.00) Sub2-5 m/z=545.17(C ₃₇ H ₂₄ ClN ₃ =546.07) Sub2-6 m/z=545.17(C ₃₇ H ₂₄ ClN ₃ =546.07) Sub2-7 m/z=545.17(C ₃₇ H ₂₄ ClN ₃ =546.07) Sub2-8 m/z=621.20(C ₄₃ H ₂₈ ClN ₃ =622.17) Sub2-9 m/z=595.18(C ₄₁ H ₂₆ ClN ₃ =596.13) Sub2-10 m/z=595.18(C ₄₁ H ₂₆ ClN ₃ =596.13) Sub2-11 m/z=645.20(C ₄₅ H ₂₈ ClN ₃ =646.19) Sub2-12 m/z=519.15(C ₃₅ H ₂₂ ClN ₃ =520.03) Sub2-13 m/z=595.18(C ₄₁ H ₂₆ ClN ₃ =596.13) Sub2-14 m/z=519.15(C ₃₅ H ₂₂ ClN ₃ =520.03) Sub2-15 m/z=595.18(C ₄₁ H ₂₆ ClN ₃ =596.13) Sub2-16 m/z=595.18(C ₄₁ H ₂₆ ClN ₃ =596.13) Sub2-17 m/z=695.21(C ₄₉ H ₃₀ ClN ₃ =696.25) Sub2-18 m/z=569.17(C ₃₉ H ₂₄ ClN ₃ =570.09) Sub2-19 m/z=569.17(C ₃₉ H ₂₄ ClN ₃ =570.09)

III. Final product synthesis

1. P-1 synthesis example

Sus2-1 (5.0 g, 10.7 mmol) was dissolved in THF (Tetrahydrofuran) (54 mL) in a round bottom flask, followed by Sub1-1 (3.0 g, 10.7 mmol), NaOH (1.3 g, 32.1 mmol), and Pd(PPh). ₃ ) ₄ (0.74 g, 0.64 mmol) and water (27 mL) were added and stirred at 80°C. When the reaction was completed, the extract was extracted with CH ₂ Cl ₂ and water, and the organic layer was dried over MgSO ₄ and concentrated. Afterwards, the produced compound was recrystallized by applying a silica gel column to obtain 4.8 g of product (yield 77%).

2. P-8 synthesis example

After dissolving Sus2-1 (4.9 g, 10.5 mmol) in THF (53 mL) in a round bottom flask, Sub1-3 (3.0 g, 10.5 mmol), NaOH (1.3 g, 31.6 mmol), Pd(PPh ₃ ) ₄ (0.73 g, 0.63 mmol) and water (26 mL) were added, and 4.6 g of product (yield 74%) was obtained using the synthesis method of P-1 above.

3. P-9 synthesis example

After dissolving Sus2-1 (5.0 g, 10.7 mmol) in THF (54 mL) in a round bottom flask, Sub1-4 (3.0 g, 10.7 mmol), NaOH (1.3 g, 32.1 mmol), Pd(PPh ₃ ) ₄ (0.74 g, 0.64 mmol) and water (27 mL) were added, and 4.5 g of product (yield 71%) was obtained using the synthesis method of P-1 above.

4. P-16 synthesis example

After dissolving Sus2-10 (5.4 g, 9.1 mmol) in THF (45 mL) in a round bottom flask, Sub1-5 (3.0 g, 9.1 mmol), NaOH (1.1 g, 27.3 mmol), and Pd(PPh ₃ ) ₄ (0.63 g, 0.55 mmol) and water (23 mL) were added, and 5.0 g of product (yield 72%) was obtained using the synthesis method of P-1 above.

5. P-19 synthesis example

After dissolving Sus2-1 (4.3 g, 9.1 mmol) in THF (45 mL) in a round bottom flask, Sub1-7 (3.0 g, 9.1 mmol), NaOH (1.1 g, 27.3 mmol), and Pd(PPh ₃ ) ₄ (0.63 g, 0.55 mmol) and water (23 mL) were added, and 4.3 g of product (yield 75%) was obtained using the synthesis method of P-1 above.

6. P-22 synthesis example

After dissolving Sus2-1 (4.2 g, 8.9 mmol) in THF (45 mL) in a round bottom flask, Sub1-9 (3.0 g, 8.9 mmol), NaOH (1.1 g, 26.8 mmol), and Pd(PPh ₃ ) ₄ (0.62 g, 0.54 mmol) and water (22 mL) were added, and 4.2 g of product (yield 73%) was obtained using the synthesis method of P-1 above.

7. P-25 synthesis example

After dissolving Sus2-1 (4.3 g, 9.1 mmol) in THF (45 mL) in a round bottom flask, Sub1-10 (3.0 g, 9.1 mmol), NaOH (1.1 g, 27.3 mmol), and Pd(PPh ₃ ) ₄ (0.63 g, 0.55 mmol) and water (23 mL) were added, and 4.5 g of product (yield 77%) was obtained using the synthesis method of P-1 above.

8. P-30 synthesis example

After dissolving Sus2-1 (4.0 g, 8.4 mmol) in THF (42 mL) in a round bottom flask, Sub1-12 (3.0 g, 8.4 mmol), NaOH (1.0 g, 25.3 mmol), Pd(PPh ₃ ) ₄ (0.58 g, 0.51 mmol) and water (21 mL) were added, and 4.1 g of product (yield 74%) was obtained using the synthesis method of P-1 above.

9. P-34 synthesis example

After dissolving Sus2-2 (4.3 g, 9.1 mmol) in THF (45 mL) in a round bottom flask, Sub1-15 (3.0 g, 9.1 mmol), NaOH (1.1 g, 27.3 mmol), Pd(PPh ₃ ) ₄ (0.63 g, 0.55 mmol) and water (23 mL) were added, and 4.6 g of product (yield 78%) was obtained using the synthesis method of P-1 above.

10. P-40 synthesis example

After dissolving Sus2-6 (5.0 g, 9.1 mmol) in THF (45 mL) in a round bottom flask, Sub1-16 (3.0 g, 9.1 mmol), NaOH (1.1 g, 27.3 mmol), and Pd(PPh ₃ ) ₄ (0.63 g, 0.55 mmol) and water (23 mL) were added, and 5.0 g of product (yield 77%) was obtained using the synthesis method of P-1 above.

11. P-42 synthesis example

After dissolving Sus2-6 (5.0 g, 9.1 mmol) in THF (45 mL) in a round bottom flask, Sub1-17 (3.0 g, 9.1 mmol), NaOH (1.1 g, 27.3 mmol), Pd(PPh ₃ ) ₄ (0.63 g, 0.55 mmol) and water (23 mL) were added, and 4.5 g of product (yield 70%) was obtained using the synthesis method of P-1 above.

Meanwhile, the FD-MS values of compounds P-1 to P-44 of the present invention prepared according to the above synthesis examples are shown in Table 3 below.

compound FD-MS compound FD-MS P-1 m/z=587.24(C ₄₃ H ₂₉ N ₃ =587.73) P-2 m/z=637.25(C ₄₇ H ₃₁ N ₃ =637.79) P-3 m/z=663.27(C ₄₉ H ₃₃ N ₃ =663.82) P-4 m/z=592.27(C ₄₃ H ₂₄ D ₅ N ₃ =592.76) P-5 m/z=587.24(C ₄₃ H ₂₉ N ₃ =587.73) P-6 m/z=587.24(C ₄₃ H ₂₉ N ₃ =587.73) P-7 m/z=663.27(C ₄₉ H ₃₃ N ₃ =663.82) P-8 m/z=663.27(C ₄₉ H ₃₃ N ₃ =663.82) P-9 m/z=587.24(C ₄₃ H ₂₉ N ₃ =587.73) P-10 m/z=663.27(C ₄₉ H ₃₃ N ₃ =663.82) P-11 m/z=637.25(C ₄₇ H ₃₁ N ₃ =637.79) P-12 m/z=590.25(C ₄₃ H ₂₆ D ₃ N ₃ =590.74) P-13 m/z=637.25(C ₄₇ H ₃₁ N ₃ =637.79) P-14 m/z=737.28(C ₅₅ H ₃₅ N ₃ =737.91) P-15 m/z=687.27(C ₅₁ H ₃₃ N ₃ =687.85) P-16 m/z=763.3(C ₅₇ H ₃₇ N ₃ =763.94) P-17 m/z=737.28(C ₅₅ H ₃₅ N ₃ =737.91) P-18 m/z=713.28(C ₅₃ H ₃₅ N ₃ =713.88) P-19 m/z=637.25(C ₄₇ H ₃₁ N ₃ =637.79) P-20 m/z=642.28(C ₄₇ H ₂₆ D ₅ N ₃ =642.82) P-21 m/z=637.25(C ₄₇ H ₃₁ N ₃ =637.79) P-22 m/z=642.28(C ₄₇ H ₂₆ D ₅ N ₃ =642.82) P-23 m/z=813.31(C ₆₁ H ₃₉ N ₃ =814) P-24 m/z=763.3(C ₅₇ H ₃₇ N ₃ =763.94) P-25 m/z=637.25(C ₄₇ H ₃₁ N ₃ =637.79) P-26 m/z=642.28(C ₄₇ H ₂₆ D ₅ N ₃ =642.82) P-27 m/z=763.3(C ₅₇ H ₃₇ N ₃ =763.94) P-28 m/z=713.28(C ₅₃ H ₃₅ N ₃ =713.88) P-29 m/z=663.27(C ₄₉ H ₃₃ N ₃ =663.82) P-30 m/z=667.29(C ₄₉ H ₂₉ D ₄ N ₃ =667.85) P-31 m/z=815.33(C ₆₁ H ₄₁ N ₃ =816.02) P-32 m/z=713.28(C ₅₃ H ₃₅ N ₃ =713.88) P-33 m/z=637.25(C ₄₇ H ₃₁ N ₃ =637.79) P-34 m/z=642.28(C ₄₇ H ₂₆ D ₅ N ₃ =642.82) P-35 m/z=713.28(C ₅₃ H ₃₅ N ₃ =713.88) P-36 m/z=642.28(C ₄₇ H ₂₆ D ₅ N ₃ =642.82) P-37 m/z=637.25(C ₄₇ H ₃₁ N ₃ =637.79) P-38 m/z=763.3(C ₅₇ H ₃₇ N ₃ =763.94) P-39 m/z=763.3(C ₅₇ H ₃₇ N ₃ =763.94) P-40 m/z=713.28(C ₅₃ H ₃₅ N ₃ =713.88) P-41 m/z=637.25(C ₄₇ H ₃₁ N ₃ =637.79) P-42 m/z=713.28(C ₅₃ H ₃₅ N ₃ =713.88) P-43 m/z=641.28(C ₄₇ H ₂₇ D ₄ N ₃ =641.81) P-44 m/z=863.33(C ₆₅ H ₄₁ N ₃ =864.06)

Manufacturing evaluation of organic electric devices

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

An organic electroluminescent device was manufactured according to a conventional method using the compound obtained through synthesis as a light-emitting host material for the light-emitting layer. First, on the ITO layer (anode) formed on the glass substrate, N1-(naphthalen-2-yl)-N4, N4-bis(4-(naphthalen-2-yl(phenyl)amino)phenyl)-N1-phenylbenzene-1 ,4-diamine (hereinafter, 2-TNATA) film was vacuum deposited to form a 60 nm thick hole injection layer, and then 4,4-bis[N-(1-naphthyl)-N was applied as a hole transport compound on the hole injection layer. -phenylamino]biphenyl (hereinafter, -NPD) was vacuum deposited to a thickness of 50 nm to form a hole transport layer. As a light emitting auxiliary layer material, tris(4-(9H-carbazol-9-yl)phenyl)amine (hereinafter, TCTA) was vacuum deposited to a thickness of 10 nm on the top of the hole transport layer to form a light emitting auxiliary layer. After forming the light-emitting auxiliary layer, the present invention compound P-1 represented by Chemical Formula 1-1 and the following compound C-1 were used in a weight ratio (5:5) as a host on the top of the light-emitting auxiliary layer, and as a dopant material ( piq) ₂ Ir(acac) was doped at a weight ratio of 95:5 to deposit a light emitting layer with a thickness of 30 nm. Next, (1,1'-bisphenyl)-4-oleato)bis(2-methyl-8-quinolineoleato)aluminum (hereinafter referred to as BAlq) was vacuum deposited to a thickness of 10 nm as a hole blocking layer, and bis(10-) was deposited as an electron transport layer. Hydroxybenzo[h]quinolinato)beryllium (hereinafter referred to as Alq3) was formed into a film with a thickness of 25 nm. Afterwards, LiF, an alkali metal halide, was deposited to a thickness of 0.2 nm as an electron injection layer, and then Al was deposited to a thickness of 150 nm and used as a cathode to manufacture an organic electroluminescent device.

[Example 2] to [Example 22]

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

[Comparative Example 1] to [Comparative Example 3]

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

<Comparative compound A> <Comparative compound B>

<Comparative compound C>

<Compound C-1> <Compound C-2>

A forward bias direct current voltage was applied to the organic electric devices prepared in Examples 1 to 22 and Comparative Examples 1 to 3 to produce electroluminescence (EL) using PR-650 manufactured by Photo Research. The characteristics were measured, and as a result of the measurement, the T95 lifespan was measured using a lifespan measurement equipment manufactured by McScience at a standard luminance of 2500 cd/m ² . Table 4 below shows the results of device fabrication and evaluation.

first compound second compound driving voltage Current (mA/cm ² ) Luminance (cd/m ² ) Efficiency (cd/A) T(95) Comparative Example 1 Comparative compound A Compound (C-1) 5.7 14.5 2500 17.3 96.5 Comparative example 2 Comparative compound B Compound (C-1) 5.6 14.0 2500 17.9 102.6 Comparative example 3 Comparative compound C Compound (C-1) 5.8 14.8 2500 16.9 97.7 Example 1 Compound (P-1) Compound (C-1) 5.0 8.1 2500 30.9 130.6 Example 2 Compound (P-1) Compound (C-2) 4.9 7.9 2500 31.7 126.2 Example 3 Compound (P-4) Compound (C-1) 4.9 8.1 2500 30.8 130.6 Example 4 Compound (P-4) Compound (C-2) 4.9 7.9 2500 31.7 126.2 Example 5 Compound (P-5) Compound (C-1) 5.0 10.0 2500 24.9 129.3 Example 6 Compound (P-5) Compound (C-2) 5.0 9.8 2500 25.6 125.0 Example 7 Compound (P-9) Compound (C-1) 5.1 10.5 2500 23.8 126.8 Example 8 Compound (P-9) Compound (C-2) 5.0 10.2 2500 24.4 122.6 Example 9 Compound (P-13) Compound (C-1) 4.9 9.8 2500 25.4 135.7 Example 10 Compound (P-13) Compound (C-2) 4.9 9.6 2500 26.1 131.1 Example 11 Compound (P-18) Compound (C-1) 5.0 10.1 2500 24.7 131.8 Example 12 Compound (P-18) Compound (C-2) 4.9 9.8 2500 25.4 127.4 Example 13 Compound (P-22) Compound (C-1) 4.9 9.7 2500 25.9 133.1 Example 14 Compound (P-22) Compound (C-2) 4.9 9.4 2500 26.6 128.6 Example 15 Compound (P-25) Compound (C-1) 4.9 8.0 2500 31.3 140.6 Example 16 Compound (P-25) Compound (C-2) 4.9 7.8 2500 32.2 136.0 Example 17 Compound (P-32) Compound (C-1) 4.9 9.3 2500 26.8 128.0 Example 18 Compound (P-32) Compound (C-2) 4.9 9.1 2500 27.6 123.7 Example 19 Compound (P-34) Compound (C-1) 4.9 8.5 2500 29.5 138.2 Example 20 Compound (P-34) Compound (C-2) 4.9 8.3 2500 30.3 133.5 Example 21 Compound (P-40) Compound (C-1) 4.9 9.1 2500 27.5 135.6 Example 22 Compound (P-40) Compound (C-2) 4.9 8.8 2500 28.3 131.2

As can be seen in Table 4, it can be seen that when the compound of the present invention is used as the light emitting layer host material, the performance of the device is greatly improved compared to Comparative Examples 1 to 3.

When comparing the compound of the present invention represented by Formula 1-1 and Comparative Compound A to Comparative Compound C, the types of substituents bonded to the triazine are different, and the mobility varies depending on the type of substituent. In other words, the drive, efficiency, and lifespan are determined by the ease of injection of holes and electrons into the dopant. If the ratio of holes and electrons (charge balance) is maintained appropriately, the efficiency and lifespan increase dramatically. It is believed that this effect is shown, and this is expected to affect the charge balance depending on the respective mobility degrees of the first compound and the second compound.

In terms of overall characteristics, the compounds of the present invention represented by Chemical Formula 1-1 have high electronic stability, and thus exhibit high electrical stability and long lifespan compared to comparative compounds. Comparing the compounds of the present invention, it can be seen that device performance is determined depending on the components of the compounds. In terms of driving voltage, it is highly dependent on the overall EOD and HOD, and it can be seen that this mobility is determined by the type of substituent the compound has, and the efficiency aspect is determined by the balance of electrons and holes of heterogeneous compounds. there is. As a result, the performance of the device is greatly affected depending on the type and bonding position of the substituent substituted within the same skeleton.

The above description is merely an exemplary description of the present invention, and those skilled in the art will be able to make various modifications without departing from the essential characteristics of the present invention. Accordingly, the embodiments disclosed in this specification are for illustrative purposes rather than limiting 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 in accordance with the claims below, and all technologies within the equivalent scope should be interpreted as being included in the scope of rights of the present invention.

100, 200, 300: organic electric element 110: first electrode
120: hole injection layer 130: hole transport layer
140: light emitting layer 150: electron transport layer
160: electron injection layer 170: second electrode
180: Light efficiency improvement layer 210: Buffer layer
220: Light-emitting auxiliary layer 320: First hole injection layer
330: first hole transport layer 340: first light emitting layer
350: first electron transport layer 360: first charge generation layer
361: second charge generation layer 420: second hole injection layer
430: second hole transport layer 440: second light emitting layer
450: Second electron transport layer CGL: Charge generation layer
ST1: 1st stack ST2: 2nd stack

Claims (17)

Compound represented by the following formula 1-1:
<Formula 1-1>

{In Formula 1-1,
1) L ¹ is a substituent represented by any of the following formulas L-1 to L-4,
<Formula L-1><FormulaL-2><FormulaL-3><FormulaL-4>

2) L ² is a single bond; or an arylene group of C ₆ to C ₆₀ ;
3) Ar is an aryl group from C ₆ to C ₆₀ ,
4) Ring A has the following formula (a); or a substituent represented by formula b;
<Formula a><Formulab>

5) R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ⁶ are each the same or different and, independently of each other, hydrogen; or deuterium;
6) R ⁷ is hydrogen; or deuterium;
7) a and d are independently integers from 0 to 5, b and f are independently integers from 0 to 6, c, e, g and h are independently integers from 0 to 4, and i is It is an integer from 0 to 7,
8) The * above refers to the binding position,
9) Here, the aryl group and the arylene group are each hydrogen; C ₆ ~ C ₂₀ aryl group; and a C ₆ to C ₂₀ aryl group substituted with deuterium; and may be further substituted with one or more substituents selected from the group consisting of.}
The compound according to claim 1, wherein Formula 1-1 is represented by any one of the following Formulas 1-1-1 to Formula 1-1-5:
<Formula 1-1-1><Formula1-1-2>

<Formula 1-1-3><Formula1-1-4>

<Formula 1-1-5>

{In Formulas 1-1-1 to 1-1-5, R ^{1 ,} R ² , R ^{3 , R 4} , R ⁵ , R ⁶ , R ⁷ , L ² , Ar, a, b, c, d , e, f, g, h and i are the same as defined in claim 1.}
The compound according to claim 1, wherein Formula 1-1 is represented by any one of the following Formulas 1-1-1-a to Formula 1-1-1-c:
<Formula 1-1-1-a><Formula1-1-1-b>

<Formula 1-1-1-c>

{In Formula 1-1-1-a to Formula 1-1-1-c, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , L ² , Ar, a, b, c, d and e is as defined in claim 1 above.}
The compound according to claim 1, wherein Formula 1-1 is represented by any one of the following Formulas 1-1-2-a to Formula 1-1-2-c:
<Formula 1-1-2-a><Formula1-1-2-b>

<Formula 1-1-2-c>

{In Formula 1-1-2-a to Formula 1-1-2-c, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , L ² , Ar, a, b, c, d and f is as defined in claim 1 above.}
The compound according to claim 1, wherein Formula 1-1 is represented by Formula 1-1-3-a or Formula 1-1-3-b.
<Formula 1-1-3-a><Formula1-1-3-b>

{In Formula 1-1-3-a or Formula 1-1-3-b, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , L ² , Ar, a, b, c, d and f is as defined in claim 1 above.}
The compound according to claim 1, wherein Formula 1-1 is represented by the following Formula 1-1-4-a:
<Formula 1-1-4-a>

{In the above formula 1-1-4-a, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , L ² , Ar, a, b, c, d, g and h are as defined in claim 1 As defined in.}
The compound according to claim 1, wherein Formula 1-1 is represented by Formula 1-1-4-b or Formula 1-1-4-c.
<Formula 1-1-4-b><Formula1-1-4-c>

{In Formula 1-1-4-b or Formula 1-1-4-c, R ¹ , R ² , R ³ , R 4 , R ⁵ , ^{R 6 ,} L ² , Ar, a, b, c, d, g and h are as defined in claim 1 above.}
The compound according to claim 1, wherein Formula 1-1 is represented by any one of the following Formulas 1-1-5-a to Formula 1-1-5-c:
<Formula 1-1-5-a><Formula1-1-5-b>

<Formula 1-1-5-c>

{In Formula 1-1-5-a to Formula 1-1-5-c, R ¹ , R ² , R ³ , R ⁵ , R ⁷ , L ² , Ar, a, b, c, e and i is as defined in claim 1 above.}
The compound according to claim 1, wherein the compound represented by Formula 1-1 is any one of the following compounds P-1 to P-44:











An organic electric device comprising an anode, a cathode, and an organic material layer formed between the anode and the cathode, wherein the organic material layer contains a single compound or two or more compounds represented by the formula 1-1 of claim 1.
The organic electric device of claim 10, wherein the organic material layer includes 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 organic electric device according to claim 10, wherein the organic material layer is a light-emitting layer.
The organic electric device of claim 10, further comprising a light efficiency improvement layer formed on at least one side of the anode and the cathode opposite to the organic material layer.
The organic electric device according to claim 10, wherein the organic material layer includes two or more stacks including a hole transport layer, a light emitting layer, and an electron transport layer sequentially formed on the anode.
The organic electric device of claim 14, wherein the organic material layer further includes a charge generation layer formed between the two or more stacks.
A display device including the organic electric element of claim 10; and a control unit that drives the display device.
The organic electric device according to claim 10, wherein the organic electric device is at least one of an organic electroluminescent device, an organic solar cell, an organic photoreceptor, an organic transistor, and a monochromatic or white lighting device.