KR102471570B1 - Compound for organic electronic element, organic electronic element comprising the same, and electronic device thereof - Google Patents

Abstract

Disclosed are an organic electric device including a compound represented by Chemical Formula 1, a first electrode, a second electrode, and an organic material layer between the first electrode and the second electrode, and an electronic device including the organic electric device. By including the compound represented by Chemical Formula 1 in the organic material layer, the driving voltage of the organic electric element can be lowered and the luminous efficiency and lifetime can be improved.

Description

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

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

In general, the organic light emitting phenomenon refers to a phenomenon in which electrical energy is converted into light energy using an organic material. An organic electric device using an organic light emitting phenomenon usually has a structure including an anode, a cathode, and an organic material layer therebetween. 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 include, 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 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, according to their functions. In addition, the light emitting material can be classified into a high molecular weight type and a low molecular weight type according to molecular weight, and can be classified into a fluorescent material derived from a singlet excited state of electrons and a phosphorescent material derived from a triplet excited state of electrons according to a light emitting mechanism. can In addition, light emitting materials may be classified into blue, green, and red light emitting materials and yellow and orange light emitting materials required to realize better natural colors according to the light emitting color.

On the other hand, when only one material is used as a light emitting material, the maximum emission wavelength moves to a longer wavelength due to intermolecular interactions, and the color purity decreases or the efficiency of the device decreases due to the emission attenuation effect. Therefore, color purity increases and energy transfer A host/dopant system may be used as a light emitting material in order to increase luminous efficiency. The principle is that when a small amount of a dopant having 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 to emit light with high efficiency. At this time, since the wavelength of the host moves to the wavelength range 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 tends to increase with large-area displays, and as a result, power consumption greater than that required for existing portable displays is required. Therefore, power consumption has become a very important factor for portable displays that have a limited power supply source such as a battery, and efficiency and lifespan problems must also be solved.

Efficiency, lifespan, driving voltage, etc. are related to each other, and as efficiency increases, driving voltage relatively decreases. indicates a tendency to increase life expectancy. However, efficiency cannot be maximized by simply improving the organic layer. This is because long life and high efficiency can be achieved at the same time when the optimal combination of the energy level and T ₁ value between each organic material layer and the intrinsic properties of the material (mobility, interfacial property, etc.) is achieved. .

Therefore, it is necessary to develop a light emitting material that has high thermal stability and can efficiently balance charge in the light emitting layer. That is, in order to fully exhibit the excellent characteristics of organic electric devices, materials constituting the organic layer in the device, such as hole injection materials, hole transport materials, light emitting materials, electron transport materials, electron injection materials, etc. are supported by stable and efficient materials. Although this should be preceded, development of stable and efficient organic material layer materials for organic electric devices has not yet been sufficiently achieved, and in particular, development of a host material for 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 the device and improving the luminous efficiency and lifetime of the device, an organic electric device using the same, and an electronic device thereof.

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

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

By using the compound according to the embodiment of the present invention, the driving voltage of the device can be lowered, and the luminous efficiency and lifespan of the device can be remarkably improved.

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

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 be described as a 'name of a group reflecting a valence', but described as a 'parent compound name' You may. For example, in the case of 'phenanthrene', which is a kind of aryl group, the name of the group may be described by dividing the valence, such as 'phenanthryl' for a monovalent group and 'phenanthrylene' for a divalent group, but the valence and Regardless, it can also be described as 'phenanthrene', which is the name of the parent compound. Similarly, in the case of pyrimidine, it can also be described as 'pyrimidine' regardless of the valence, or as the 'name of the group' of the corresponding valence, such as a pyrimidinyl group in the case of monovalent, or pyrimidinylene in the case of divalent. have.

As used herein, the term "fluorenyl group" or "fluorenylene group" means a monovalent or divalent functional group in which R, R' and R" are all hydrogen in the following structure, respectively, unless otherwise specified, " Substituted fluorenyl group" or "substituted fluorenyl 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 This includes cases where they form a spy compound together.

As used herein, the term "spiro compound" has a 'spiro union', which means a connection formed by two rings sharing only one atom. At this time, the atoms shared by the two rings are called 'spiro atoms', and according to the number of spiro atoms in a compound, they are called 'monospiro-', 'dispiro-', and 'trispiro-', respectively. ' It's called a compound.

As used herein, the term "heterocyclic group" refers to a ring containing heteroatoms such as N, O, S, P or Si instead of carbon forming a ring, and is referred to as a "heteroaryl group" or "heteroarylene group". It includes not only an aromatic ring but also a non-aromatic ring, such as the following compound instead of carbon forming a ring, SO ₂ , and a compound containing a heteroatom group such as P=O may also be included.

In addition, unless explicitly stated otherwise, the chemical formula used in the present invention applies the same as the substituent definition by the exponent definition of the following formula.

Here, when a is an integer of 0, substituent R ¹ does not exist, and when a is an integer of 1, one substituent R ¹ is bonded to any one of the carbon atoms forming the benzene ring, and when a is an integer of 2 or 3 Each is combined as follows, wherein 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 the hydrogen bonded to the carbon forming the benzene ring is omit

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

1 is a diagram illustrating a stacked structure of an organic electric element according to an embodiment of the present invention.

Referring to FIG. 1, an organic electric element 100 according to the present invention includes a first electrode 120, a second electrode 180, and a first electrode 110 and a second electrode 180 formed on a substrate 110. ) is provided with an organic material layer containing the compound according to the present invention. In this case, the first electrode 120 may be an anode (anode), and the second electrode 180 may be a cathode (negative electrode), 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 sequentially include a hole injection layer 130 , a hole transport layer 140 , a light emitting layer 150 , an electron transport layer 160 , and an electron injection layer 170 on the first electrode 120 . At this time, at least one of these layers may be omitted, or a hole blocking layer, an electron blocking layer, a light emitting auxiliary layer 151, a buffer layer 141, and the like may be further included, and the electron transport layer 160 and the like may serve as the hole blocking layer. Maybe.

In addition, although not shown, the organic electric element according to the present invention may further include a protective layer or a capping layer formed on a surface opposite to the organic material layer among at least one surface of the first electrode and the second electrode.

The compound according to the present invention applied to the organic layer is a hole injection layer 130, a hole transport layer 140, an electron transport layer 160, an electron injection layer 170, a light emitting layer 150, a light efficiency improving layer, a light emitting auxiliary layer, etc. can be used as a material for For example, the compound of the present invention may be used as a material of the light emitting layer 150, preferably a host material of the light emitting layer.

An organic light emitting device according to an embodiment of the present invention may be manufactured using various deposition methods. It can be manufactured using a deposition method such as PVD or CVD, for example, depositing a metal or a metal oxide having conductivity 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 a hole transport layer 140, a light emitting layer 150, an electron transport layer 160 and an electron injection layer 170, it can be manufactured by depositing a material that can be used as the cathode 180 thereon. have. In addition, an auxiliary light emitting layer 151 may be additionally formed between the hole transport layer 140 and the light emitting layer 150 .

In addition, the organic layer may be formed by a solution process or a solvent process using various polymer materials, such as a spin coating process, a nozzle printing process, an inkjet printing process, a slot coating process, a dip coating process, a roll-to-roll process, a doctor blading process, It can be manufactured with fewer layers by a method such as a screen printing process or a thermal transfer method. Since the organic layer according to the present invention can be formed in various ways, the scope of the present invention is not limited by the forming method.

The organic electric device according to the present invention may be one of an organic light emitting device (OLED), an organic solar cell, an organic photoconductor (OPC), an organic transistor (organic TFT), a device for monochromatic or white lighting, and a device for quantum dot display.

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 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 a mobile communication terminal such as a mobile phone, a PDA, an electronic dictionary, a PMP, a remote control, a navigation device, a game machine, various TVs, and various computers. The display device may include an organic light emitting display, a quantum dot display, and the like.

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

A compound according to one aspect of the present invention is represented by Formula 1 below.

<Formula 1>

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

X is O, S or C(R')(R"), and ring A is a C ₆ -C ₆₀ aromatic ring.

Ring A is preferably a C ₆ ~ C ₁₈ aromatic ring, more preferably a C ₆ ~ C ₁₀ aromatic ring, and examples thereof include benzene, naphthalene, and phenanthrene.

Wherein R' and R" are each independently selected from: i) a C ₆ ~ C ₆₀ aryl group; a fluorenyl group; a C ₂ ~ C ₆₀ hetero atom including at least one heteroatom selected from O, N, S, Si, and P; Cyclic group; C ₃ ~ C ₆₀ aliphatic ring group; C ₃ ~ C ₆₀ aliphatic ring and C ₆ ~ C ₆₀ aromatic ring fused ring group; C ₁ ~ C ₅₀ alkyl group; C ₂ ~ C ₂₀ alkene Diary; C ₂ ~ C ₂₀ alkynyl group; C ₁ ~ C ₃₀ alkoxyl group; C ₆ ~ C ₃₀ aryloxy group; and -L'-N (R _a ) (R _b ) selected from the group consisting of , ii) connected to each other to form a ring selected from the group consisting of C ₆ ~ C ₆₀ aromatic hydrocarbons, C ₂ ~ C ₆₀ heterocycles, C ₃ ~ C ₆₀ aliphatic rings, and combinations thereof. R' and R" may be methyl, phenyl, and the like.

R ¹ and R ² are each independently hydrogen; heavy hydrogen; halogen; C ₆ ~ C ₆₀ aryl group; fluorenyl group; A C ₂ ~C ₆₀ heterocyclic group containing at least one heteroatom selected from 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; C ₁ ~ C ₅₀ Alkyl group; A C ₂ ~C ₂₀ alkenyl group; A C ₂ ~C ₂₀ alkynyl group; C ₁ ~ C ₃₀ alkoxyl group; C ₆ ~ C ₃₀ aryloxy group; And -L'-N (R _a ) (R _b ); may be selected from the group consisting of.

R ³ is: i) independently of each other hydrogen; heavy hydrogen; halogen; C ₆ ~ C ₆₀ aryl group; fluorenyl group; A C ₂ ~C ₆₀ heterocyclic group containing at least one heteroatom selected from 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; C ₁ ~ C ₅₀ Alkyl group; A C ₂ ~C ₂₀ alkenyl group; A C ₂ ~C ₂₀ alkynyl group; C ₁ ~ C ₃₀ alkoxyl group; C ₆ ~ C ₃₀ aryloxy group; and -L'-N(R _a )(R _b ); or ii) adjacent groups are connected to each other to form C ₆ ~ C ₆₀ aromatic hydrocarbons, C ₂ ~ C ₆₀ heterocycles, C A ring selected from the group consisting of ₃ ~ C ₆₀ aliphatic rings and combinations thereof may be formed.

m is an integer from 0 to 16, n is an integer from 0 to 4, l is an integer from 0 to 2, and when each of these is an integer of 2 or more, each R ¹ , each R ² , and each R ³ are mutually may be the same or different.

L' is a single bond; C ₆ ~ C ₆₀ arylene group; Fluorenylene group; A C ₂ ~C ₆₀ heterocyclic group containing at least one heteroatom selected from O, N, S, Si, and P; C ₃ ~ C ₆₀ aliphatic ring group; and C ₃ ~ C ₆₀ aliphatic ring and C ₆ ~ C ₆₀ aromatic ring fused ring group; may be selected from the group consisting of.

Wherein R _a and R _b are each independently hydrogen; C ₆ ~ C ₆₀ aryl group; fluorenyl group; A C ₂ ~C ₆₀ heterocyclic group containing at least one heteroatom selected from O, N, S, Si, and P; C ₃ ~ C ₆₀ aliphatic ring group; and C ₃ ~ C ₆₀ aliphatic ring and C ₆ ~ C ₆₀ aromatic ring fused ring group; may be selected from the group consisting of.

When R ¹ to R ³ are aryl groups, they are preferably C ₆ -C ₃₀ aryl groups, more preferably C ₆ -C ₁₂ aryl groups, such as phenyl, biphenyl, naphthyl, and the like. When R ¹ to R ³ are heterocyclic groups, preferably C ₂ ~ C ₃₀ heterocyclic groups, more preferably C ₂ ~ C ₁₈ heterocyclic groups such as pyridine, pyrimidine, triazine, carbazole, phenylcarbazole, quinazoline, benzoquinazoline, dibenzoquinazoline, pyridoimidazoindole and the like.

Also, R ¹ to R ³ may be dimethylfluorene, diphenylfluorene, bifluorene, cyclohexane or the like.

In addition, when R ¹ to R ³ are -L'-N(R _a )(R _b ), L' may be a single bond, phenyl, naphthyl, biphenyl, etc., and R _a and R _b are phenyl, bi phenyl, naphthyl, and the like.

L is a single bond; C ₆ ~ C ₆₀ arylene group; Fluorenylene group; A C ₂ ~C ₆₀ heterocyclic group containing at least one heteroatom selected from O, N, S, Si, and P; C ₃ ~ C ₆₀ aliphatic ring group; and C ₃ ~ C ₆₀ aliphatic ring and C ₆ ~ C ₆₀ aromatic ring fused ring group; may be selected from the group consisting of.

When L is an arylene group, it is preferably a C ₆ -C ₃₀ arylene group, more preferably a C ₆ -C ₁₄ arylene group, such as phenyl, naphthyl, biphenyl, anthracene, and the like. When L is a heterocyclic group, it is preferably a C ₂ -C ₃₀ heterocyclic group, more preferably a C ₂ -C ₁₆ heterocyclic group, such as pyridine, pyrimidine, triazine, imidazole, and phenylimida. Sol, quinazoline, benzoquinazoline, dibenzoquinazoline, quinoxaline, carbazole, cinnoline, phenoxatine, benzothienopyridine, benzothienopyrimidine, benzofuropyrimidine, benzonaphthothiophene , naphthofuropyrimidine, naphthocyenopyrimidine, and the like.

Ar ₁ is a C ₆ ~ C ₆₀ aryl group; fluorenyl group; A C ₂ ~C ₆₀ heterocyclic group containing at least one heteroatom selected from 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; C ₁ ~ C ₅₀ Alkyl group; A C ₂ ~C ₂₀ alkenyl group; A C ₂ ~C ₂₀ alkynyl group; C ₁ ~ C ₃₀ alkoxyl group; C ₆ ~ C ₃₀ aryloxy group; And -L'-N (R _a ) (R _b ) It may be selected from the group consisting of. At this time, L', R _a and R _b are as defined above.

When Ar ₁ is an aryl group, it is preferably a C ₆ -C ₃₀ aryl group, more preferably a C ₆ -C ₁₈ aryl group, such as phenyl, biphenyl, naphthyl, anthracene, phenanthrene, terphenyl, pyrene, triphenylene, and the like. When Ar ₁ is a heterocyclic group, it is preferably a C ₂ ~ C ₃₀ heterocyclic group, more preferably a C ₂ ~ C ₂₂ heterocyclic group, such as pyridine, pyrimidine, triazine, imidazole, or phenyl. Midazole, quinazoline, indenoquinazoline, benzoquinazoline, dibenzoquinazoline, benzothiophene, dibenzothiophene, dibenzofuran, benzonaphthothiophene, benzonaphthofuran, benzothienopyridine, Benzothyenopyrimidines, benzofuropyrimidines, phenylimidazoles, naphthofuropyrimidines, naphthothyenopyrimidines, phenyl-benzopyrimidoindoles, phenylpyrimidoindoles, carbazoles, phenylcarbazoles , benzocarbazole, benzoimidazoquinoxaline, dihydrobenzoimidazotriazine (10,10a-dihydrobenzo[4,5]imidazo[1,2-a][1,3,5]triazine), phenoxatine, Benzo-benzothienocarbazole (14H-benzo[c]benzo[4,5]thieno[2,3-a]carbazole), pyridoimidazoindole (5a,10b-dihydro-6H-pyrido[1 ',2':1,2]imidazo[4,5-b]indole), diphenyl-dihydroacridine (9,9-diphenyl-9,10-dihydroacridine), quinoxaline, cinnoline, cyan may be a tren or the like. When Ar ₁ is a fluorenyl group, it may be dimethylfluorene, diphenylfluorene, bifluorene or the like. When Ar ₁ is an alkyl group, it may be preferably a C ₁ to C ₁₀ alkyl group, more preferably a C ₁ to C ₄ alkyl group such as t-butyl. Also, Ar ₁ may be 9,9-dimethyl-9H-indenophenanthrene.

o1, o2 and o3 are integers of 0 or 1, respectively, and m+n+l+o1+o2+o3 is an integer of 1 or greater. When m+n+l is an integer greater than or equal to 1 and o1+o2+o3 is 0, at least one of R ¹ to R ³ is a C ₆ -C ₃₀ aryl group; fluorenyl group; A C ₂ ~C ₃₀ heterocyclic group containing at least one heteroatom selected from O, N, S, Si, and P; And -L'-N (R _a ) (R _b ) It is selected from the group consisting of.

A ring formed by connecting R ¹ to R ³ , L, Ar ₁ , R', R", L', R _a , R _b , adjacent R ³ to each other, and a ring formed by connecting R' and R" to each other are each deuterium; halogen; A silane group unsubstituted or substituted with a C ₁ -C ₂₀ alkyl group or a C ₆ -C ₂₀ aryl group; Siloxane group; boron group; Germanium group; cyano group; nitro group; A phosphine oxide group unsubstituted or substituted with a C ₁ -C ₂₀ alkyl group or a C ₆ -C ₂₀ aryl group; C ₁ -C ₂₀ Alkylthio group; C ₁ -C ₂₀ alkoxyl 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; A deuterium-substituted C ₆ -C ₂₀ aryl group; fluorenyl group; A C ₂ -C ₂₀ heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P; C ₃ -C ₂₀ cycloalkyl group; C ₃ ~ C ₆₀ aliphatic ring and C ₆ ~ C ₆₀ aromatic ring fused ring group; C ₇ -C ₂₀ arylalkyl group; And a C ₈ -C ₂₀ arylalkenyl group; may be further substituted with one or more substituents selected from the group consisting of.

For example, R ¹ to R ³ may each be further substituted with phenyl, naphthyl, CN, triazine, pyridine, pyrimidine, benzothienopyrimidine, t-butyl, etc., and L is F, CN, triazine , It may be further substituted with a phenyl-substituted triazine, and Ar ₁ may be further substituted with phenyl, biphenyl, F, CN, and the like.

Chemical Formula 1 may be represented by one of Chemical Formulas 2 to 5 below.

<Formula 2> <Formula 3>

<Formula 4> <Formula 5>

In Formulas 2 to 5, X, R ¹ to R ³ , l, m, n, L, and Ar ₁ are as defined in Formula 1.

At least one of R ¹ to R ³ may be represented by Formula A-1 or A-2.

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

In Formulas A-1 and A-2, each symbol may be defined as follows.

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

R ^e is hydrogen; heavy hydrogen; halogen; A silane group unsubstituted or substituted with a C ₁ -C ₂₀ alkyl group or a C ₆ -C ₂₀ aryl group; Siloxane group; boron group; Germanium group; cyano group; nitro group; C ₁ -C ₂₀ Alkylthio group; C ₁ -C ₂₀ alkoxyl 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; A deuterium-substituted C ₆ -C ₂₀ aryl group; fluorenyl group; A C ₂ -C ₂₀ heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P; C ₃ -C ₂₀ cycloalkyl group; C ₇ -C ₂₀ arylalkyl group; and a C ₈ -C ₂₀ arylalkenyl group.

Z may be selected from the group represented by the formula below.

In the chemical formula of Z, * represents a site bonded to a ring containing Q ¹ to Q ⁴ . That is, one side marked with * is shared with a ring containing Q ¹ to Q ⁴ .

V is independently of each other N or C(R ^h ).

W ¹ and W ² are each independently a single bond, -NL ¹ -Ar ¹ S, O or C(R ^f )(R ^g ).

L ¹ is a single bond; C ₆ ~ C ₆₀ arylene group; Fluorenylene group; A C ₂ ~C ₆₀ heterocyclic group containing at least one heteroatom selected from O, N, S, Si, and P; C ₃ ~ C ₆₀ aliphatic ring group; and C ₃ ~ C ₆₀ aliphatic ring and C ₆ ~ C ₆₀ aromatic ring fused ring group; may be selected from the group consisting of.

Ar ¹ , R ^f , R ^g and R ^h are each independently a C ₆ -C ₂₀ aryl group; A deuterium-substituted C ₆ -C ₂₀ aryl group; fluorenyl group; A C ₂ -C ₂₀ heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P; C ₃ -C ₂₀ cycloalkyl group; C ₃ ~ C ₆₀ aliphatic ring and C ₆ ~ C ₆₀ aromatic ring fused ring group; C ₁ -C ₂₀ Alkylthio group; C ₁ -C ₂₀ alkoxyl group; C ₁ -C ₂₀ Alkyl group; C ₂ -C ₂₀ alkenyl group; C ₂ -C ₂₀ alkynyl group; C ₇ -C ₂₀ arylalkyl group; And a C ₈ -C ₂₀ arylalkenyl group; selected from the group consisting of, R ^f and R ^g may be bonded to each other to form a ring.

Specifically, the compound represented by Formula 1 may be one of the following compounds.

.

.

As another embodiment of the present invention, there is provided 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 1 represented by Formula 1 A single species compound or a mixture of two or more species is included.

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, and preferably, the compound or mixture is included in the light emitting layer.

As another embodiment of the present invention, an electronic device including a display device including the organic electronic element and a control unit driving the display device is provided.

Hereinafter, a synthesis example of a compound represented by the chemical formula according to the present invention and a manufacturing example of an organic electric device will be described in detail with examples, but the present invention is not limited to the following examples.

synthesis example

The compound (final products) according to the present invention is synthesized by reacting the core and the sub as shown in Scheme 1 below, but is not limited thereto.

<Scheme 1>

(G is pinacolatoborane, Hal is Br or Cl)

Core's synthesis example

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

<Scheme 2>

of Core 1 synthesis example

Core 1 may be synthesized by the reaction pathways of Schemes 2-1, 2-2 and 2-3 below, but is not limited thereto.

<Scheme 2-1>

Synthesis of SM-3

In a round bottom flask, 4-chloro-3,6-dibromoaniline (SM-1) (1 eq), CuI (0.2 eq), 1,10-phenanthroline (0.4 eq), Cs ₂ CO ₃ (3 equivalents) was added and then xylene was added and stirred at room temperature. Thereafter, 2-iodopyridine (SM-2) (1.2 eq.) was added and the reaction proceeded at 120°C. After the reaction was completed, the temperature was lowered to room temperature, extracted with ethyl acetate and water, and the organic layer was dried over Na ₂ SO ₄ and concentrated. Thereafter, the concentrate was passed through a silica gel column and recrystallized to obtain product SM-3. (Yield: 65%)

<Scheme 2-2>

Synthesis of SM-4

In a round bottom flask, SM-3 (1 eq.), 2-methylthiophenyl boronic acid (1.05 eq.), Pd(PPh ₃ ) ₄ (0.03 eq.), K ₂ CO ₃ After adding (3 equivalents), THF/H ₂ O was added at a ratio of 2:1 and reacted while refluxing at 70°C. After the reaction was completed, the temperature was lowered to room temperature, extracted with CH ₂ Cl ₂ and water, and the organic layer was dried over MgSO ₄ and concentrated. Thereafter, the concentrate was passed through a silica gel column and recrystallized to obtain product SM-4. (Yield: 75%)

Synthesis of SM-5

After dissolving SM-4 in THF and acetic acid in a round bottom flask, hydrogen peroxide (35%) was slowly added dropwise. After stirring at room temperature for 10 hours, the reaction was concentrated to remove the solvent, extracted with CH ₂ Cl ₂ and water, and the organic layer was dried over MgSO ₄ and concentrated to obtain SM-5.

Synthesis of SM-6

After dissolving SM-5 in trifluoromethane sulfonic acid in a round bottom flask and stirring at room temperature, pyridine/purified water was added dropwise, and the temperature was raised to reflux at 120°C. Upon completion of the reaction, the organic layer was extracted with CH ₂ Cl ₂ , passed through a silica gel column, and then recrystallized to obtain product SM-6.

<Scheme 2-3>

SM-6 (1 equiv.), Bis(pinacolato)diboron (1.5 equiv.), PdCl ₂ (dppf) (0.03 equiv.), and KOAc (3 equiv.) were added to a round bottom flask, and DMF was added thereto, followed by reaction at 100°C. After the reaction was completed, the temperature was lowered to room temperature, and water was added and stirred. Then, the resulting crude solid was filtered through a filter and dissolved in CH ₂ Cl ₂ . Thereafter, after filtering with an emulsion filter (Elusion filter), it was concentrated and recrystallized to obtain Core 1.

<Scheme 3>

of Core 2 synthesis example

Core 2 may be synthesized by the reaction pathways of Scheme 3-1 and Scheme 3-2 below, but is not limited thereto.

<Scheme 3-1>

Synthesis of SM-9

In a round bottom flask, SM-3 (1 eq.), 2-hydroxyphenylboronic acid (1.05 eq.), Pd(PPh ₃ ) ₄ (0.03 eq.), K ₂ CO ₃ After adding (3 equivalents), THF/H ₂ O was added at a ratio of 2:1 and reacted under reflux at 70°C. After the reaction was completed, the temperature was lowered to room temperature, extracted with CH ₂ Cl ₂ and water, and the organic layer was dried over MgSO ₄ and concentrated. (Yield: 67%)

Synthesis of SM-10

Put SM-9 (1 equiv), tert-butylperoxybenzoate (2.1 equiv), Pd(OAc) ₂ (0.03 equiv), 3-nitropyridine (0.1 equiv) in a round bottom flask, dissolve in 1,2-dimethoxyethane, and heat to 150℃. reflux reaction. When the reaction was completed, the temperature was lowered to room temperature, and the organic layer was extracted with CH ₂ Cl ₂ . After passing through a silica gel column, it was recrystallized to obtain SM-10. (Yield: 70%)

<Scheme 3-2>

SM-10 (1 equiv.), Bis(pinacolato)diboron (1.5 equiv.), PdCl ₂ (dppf) (0.03 equiv.), and KOAc (3 equiv.) were added to a round bottom flask, DMF was added, and the reaction proceeded at 100°C. made it When the reaction was complete, the temperature was lowered to room temperature, and water was added and stirred. Then, the resulting crude solid was filtered through a filter and dissolved in CH ₂ Cl ₂ . Thereafter, after filtering with an emulsion filter (Elusion filter), it was concentrated and recrystallized to obtain Core 2.

<Scheme 4>

Core 3's synthesis example

Core 3 may be synthesized by the reaction pathways of Scheme 4-1, Scheme 4-2, Scheme 4-3 and Scheme 4-4 below, but is not limited thereto.

<Scheme 4-1>

Synthesis of SM-3

In a round bottom flask, 4-chloro-3,6-dibromoaniline (SM-1) (1 eq), CuI (0.2 eq), 1,10-phenanthroline (0.4 eq), Cs ₂ CO ₃ (3 equivalents) was added and xylene was stirred at room temperature. Thereafter, 2-iodopyridine (SM-2) (1.2 eq.) was added and the reaction proceeded at 120°C. After the reaction was completed, the temperature was lowered to room temperature, extracted with ethyl acetate and water, and the organic layer was dried over Na ₂ SO ₄ and concentrated. The concentrate was passed through a silica gel column and recrystallized to obtain SM-3. (Yield: 65%)

Synthesis of SM-11

In a round bottom flask, SM-3 (1 eq), 2-iodoboronic acid (1 eq), Pd(PPh ₃ ) ₄ (0.03 eq), K ₂ CO ₃ (3 equivalents) was added, and THF/H ₂ O was added at a ratio of 2:1, followed by a reflux reaction at 70°C. After the reaction was completed, the temperature was lowered to room temperature, extracted with ethyl acetate and water, and the organic layer was dried over Na ₂ SO ₄ and concentrated. The concentrate was passed through a silica gel column and recrystallized to obtain SM-4. (Yield: 60%)

<Scheme 4-2>

In a round bottom flask, SM-11 (1 equiv.), dibromoethane (7 equiv.), Pd(OAc) ₂ (0.1 equivalent), Add Potassium bicarbonate (8 equivalents), Potassium acetate (9 equivalents), and isopropyl alcohol (2 equivalents), add DMF / DMA / H ₂ O in a ratio of (6:2:1), and proceed with the reaction at 75℃ made it After the reaction was completed, the temperature was lowered to room temperature, extracted with ethyl acetate and water, and the organic layer was dried over Na ₂ SO ₄ and concentrated. The concentrate was passed through a silica gel column and recrystallized to obtain SM-12. (Yield: 79%)

<Scheme 4-3>

SM-12 (1 equivalent) and THF were added to the round bottom flask and stirred, the temperature was lowered to -76°C, and n-BuLi (2.5M / in Hexane) (2 equivalents) was slowly added dropwise. After 2 hours, bromomethane (1.5 equivalent) was added dropwise, and the reaction proceeded at room temperature. When the reaction is complete, the reactant is slowly added to ice water, stirred, and the precipitated solid is filtered through a filter. Then, the filtered solid was extracted with CH ₂ Cl ₂ and water, and the organic layer was dried over MgSO ₄ and concentrated. Thereafter, the concentrate was passed through a silica gel column to obtain SM-13. (Yield: 72%)

<Scheme 4-4>

SM-13 (1 equiv.), Bis(pinacolato)diboron (1.5 equiv.), PdCl ₂ (dppf) (0.03 equiv.), and KOAc (3 equiv.) were added to a round bottom flask, then DMF was added and the reaction proceeded at 100°C. let it When the reaction is complete, the temperature is lowered to room temperature, water is added and stirred, and the resulting crude solid is filtered through a filter. Thereafter, the crude solid was dissolved in CH ₂ Cl ₂ , filtered through an elusion filter, concentrated and recrystallized to obtain Core 3.

Core 4's synthesis example

Core 4 may be synthesized by the reaction pathway of Scheme 5 below, but is not limited thereto.

<Scheme 5>

Synthesis of SM-14

In a round bottom flask, SM-12 (1 equiv), Chlorobenzene (1.2 equiv), Cesium carbonate (2 equiv), Palladium acetate (0.02 equiv), PCy ₃ ^. After adding HBF ₄ (0.04 equivalent), DMA was added and reacted at 120°C. After the reaction was completed, the temperature was lowered to room temperature, extracted with ethyl acetate and water, and the organic layer was dried over Na ₂ SO ₄ and concentrated. The concentrate was passed through a silica gel column and recrystallized to obtain SM-14. (Yield: 69%)

Synthesis of Core 4

SM-14 (1 equiv.), Bis(pinacolato)diboron (1.5 equiv.), PdCl ₂ (dppf) (0.03 equiv.), and KOAc (3 equiv.) were added to a round bottom flask, and DMF was added and reacted at 100°C. After the reaction was completed, the temperature was lowered to room temperature, water was added and stirred, and the resulting crude solid was filtered through a filter. Thereafter, the crude solid was dissolved in CH ₂ Cl ₂ , filtered through an elusion filter, concentrated and recrystallized to obtain Core 4.

Core 16 synthesis example

Core 4 may be synthesized by the reaction pathway of Scheme 5 below, but is not limited thereto.

<Scheme 5>

Synthesis of SM-16

In a round bottom flask, SM-15 (1 eq.), 5-bromo-2-(methylthio)phenyl boronic acid (1.05 eq.), Pd(PPh ₃ ) ₄ (0.03 eq.), K ₂ CO ₃ After adding (3 equivalents), THF/H ₂ O was added in a ratio of 2:1 and reacted under reflux at 70°C. After the reaction was completed, the temperature was lowered to room temperature, extracted with CH ₂ Cl ₂ and water, and the organic layer was dried over MgSO ₄ and concentrated. The concentrate was passed through a silica gel column and recrystallized to obtain SM-16. (Yield: 75%)

Synthesis of SM-17

After dissolving SM-16 in THF and acetic acid in a round bottom flask, hydrogen peroxide (35%) was slowly added dropwise. After stirring at room temperature for 10 hours, the reaction was finished, concentrated to remove the solvent, and the organic layer was extracted with CH ₂ Cl ₂ and water, and then the organic layer was dried over MgSO ₄ and concentrated.

Synthesis of SM-18

Dissolve SM-17 in trifluoromethane sulfonic acid in a round bottom flask, stir at room temperature, add pyridine/purified water dropwise, and raise the temperature to reflux at 120°C. When the reaction was completed, the organic layer was extracted with CH ₂ Cl ₂ , passed through a silica gel column, and recrystallized to obtain SM-18.

Synthesis of Core 16

SM-18 (1 equiv.), Bis(pinacolato)diboron (1.5 equiv.), PdCl ₂ (dppf) (0.03 equiv.), and KOAc (3 equiv.) were added to a round bottom flask, DMF was added, and the reaction proceeded at 100°C. let it When the reaction is complete, the temperature is lowered to room temperature, water is added and stirred, and the resulting crude solid is filtered through a filter. Thereafter, the crude solid was dissolved in CH ₂ Cl ₂ , filtered through an elusion filter, concentrated and recrystallized to obtain Core 16.

An example of Core is as follows, but is not limited thereto.

[Table 1]

Sub's synthesis example

A compound belonging to Sub of Reaction Scheme 1 may be synthesized by Reaction Scheme 6 below, but is not limited thereto.

<Scheme 6>

(Hal ¹ = I, Br or Cl, and Hal ² = Br or Cl)

of Sub 29 synthesis example

In a round-bottom flask, Sub29-1 (1.0 equiv.), 4,4,5,5-tetramethyl-2-phenyl-1,3,2-dioxaborolane (1.3 equiv.), Pd(PPh ₃ ) ₄ (0.03 equiv.), K ₂ CO ₃ (3 equivalents) was added, and THF/H ₂ O was added in a ratio of 2:1, followed by a reflux reaction at 70°C. After the reaction was completed, the temperature was lowered to room temperature, extracted with CH ₂ Cl ₂ and water, and the organic layer was dried over MgSO ₄ and concentrated. Thereafter, the concentrate was passed through a silica gel column and recrystallized to obtain Sub29. (Yield: 80%)

Sub43's synthesis example

In a round bottom flask, Sub43-1 (1.0 equiv.), 4,4,5,5-tetramethyl-2-phenyl-1,3,2-dioxaborolane (1.3 equiv.), Pd(PPh ₃ ) ₄ (0.03 equiv.), K ₂ CO ₃ (3 equivalents) was added, and THF/H ₂ O was added in a ratio of 2:1, followed by a reflux reaction at 70°C. After the reaction was completed, the temperature was lowered to room temperature, extracted with CH ₂ Cl ₂ and water, and the organic layer was dried over MgSO ₄ and concentrated. Thereafter, the concentrate was passed through a silica gel column and recrystallized to obtain Sub43. (Yield: 85%)

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

[Table 2]

of the final compound synthesis example

of 1-8 synthesis example

<Scheme 7>

Put Core 1 (1.0 equiv.), Sub29 (1.1 equiv.), Pd(PPh ₃ ) ₄ (0.03 equiv.), K ₂ CO ₃ (3 equiv.), and THF/H ₂ O in a 2:1 ratio in a round bottom flask. into a reflux reaction at 70 ° C. After the reaction was completed, the temperature was lowered to room temperature, extracted with CH ₂ Cl ₂ and water, and the organic layer was dried over MgSO ₄ and concentrated. Thereafter, the concentrate was passed through a silica gel column and recrystallized to obtain Compound 1-8. (Yield: 80%)

1-58 synthesis example

<Scheme 8>

Core 8 (1.0 equiv.), Sub58 (1.1 equiv.), Pd(PPh ₃ ) ₄ (0.03 equiv.), K ₂ CO ₃ (3 equiv.), THF/H ₂ O Using the compound 1-8 synthesis method Got 1-58. (Yield: 65%)

1-69 synthesis example

<Scheme 9>

Synthesis method of Compound 1-8 using Core 8-1 (1.0 equivalent), Sub77 (1.1 equivalent), Pd(PPh ₃ ) ₄ (0.03 equivalent), K ₂ CO ₃ (3 equivalent), and THF/H ₂ O As a result, compound 1-69 was obtained. (Yield: 70%)

of 1-71 synthesis example

<Scheme 10>

Synthesis method of Compound 1-8 using Core 2-1 (1.0 equivalent), Sub78 (1.1 equivalent), Pd(PPh ₃ ) ₄ (0.03 equivalent), K ₂ CO ₃ (3 equivalent), and THF/H ₂ O As a result, compound 1-71 was obtained. (Yield: 68%)

of 1-103 synthesis example

<Scheme 11>

Core 14 (1.0 equiv.), Sub61 (1.1 equiv.), Pd(PPh ₃ ) ₄ (0.03 equiv.), K ₂ CO ₃ (3 equiv.), and THF/H ₂ O were added to the round bottom flask to prepare the above compounds 1-8. Compound 1-103 was obtained by the synthesis method. (Yield: 72%)

The FD-MS values of Compound 1-1 to Compound 1-127 of the present invention prepared according to Synthesis Example as described above are shown in Table 3 below.

[Table 3]

Manufacturing evaluation of organic electric devices

[ Example One] Red Organic electroluminescent device (phosphorescent host)

N ¹ -(naphthalen-2-yl)-N ⁴ ,N ⁴ -bis(4-(naphthalen-2-yl(phenyl)amino)phenyl)-N ¹ -phenylbenzene on the ITO layer (anode) formed on the glass substrate -1,4-diamine (hereinafter abbreviated as "2-TNATA") was vacuum deposited to a thickness of 60 nm to form a hole injection layer, and then 4,4-bis[N-(1 -Naphthyl)-N-phenylamino]biphenyl (hereinafter abbreviated as "NPD") was vacuum deposited to a thickness of 60 nm to form a hole transport layer.

Subsequently, Compound 1-2 of the present invention was used as a host material and bis-(1-phenylisoquinolyl)iridium(III)acetylacetonate (hereinafter abbreviated as “(piq) ₂ Ir(acac)”) as a dopant material on the hole transport layer. However, a light emitting layer having a thickness of 30 nm was deposited by doping dopants such that the weight ratio was 95:5.

Next, (1,1'-biphenyl-4-olato)bis(2-methyl-8-quinolinolato)aluminum (hereinafter abbreviated as "BAlq") was vacuum-deposited to a thickness of 10 nm on the light emitting layer to form a hole blocking layer. was formed, and tris(8-quinolinol) aluminum (hereinafter abbreviated as Alq ₃ ) was deposited to a thickness of 40 nm on the hole blocking layer to form an electron transport layer.

Thereafter, LiF was deposited on the electron transport layer to a thickness of 0.2 nm to form an electron injection layer, and Al was deposited on the electron injection layer to a thickness of 150 nm to form a cathode.

[ Example 2] to [ Example 35]

An organic light emitting device was manufactured in the same manner as in Example 1, except that the compound of the present invention shown in Table 4 was used instead of Compound 1-2 as a host material of the light emitting layer.

[ comparative example One]

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

<Comparative compound 1>

A forward bias DC voltage was applied to the organic electroluminescent devices prepared in Examples 1 to 37 and Comparative Example 1 of the present invention to measure electroluminescence (EL) characteristics with a PR-650 from Photoresearch, The results of measuring the life of T95 through McScience's life measurement equipment at 2500 cd / m ² standard luminance are shown in Table 4 below.

[Table 4]

As can be seen from the results of Table 4, it can be confirmed that the device using the compound according to one embodiment of the present invention as a phosphorescent host material of the light emitting layer has significantly improved electrical characteristics than the device using Comparative Compound 1 as a phosphorescent host material of the light emitting layer. can

In more detail, when the 5-ring heterocyclic compound of the present invention was used as a host material, better results were obtained in terms of driving voltage, efficiency, and lifespan than CBP (Comparative Compound 1), which is generally used as a host material.

As can be seen from Table 5 below, the compound of the present invention has a relatively lower LUMO energy level than CBP, so electron injection from the electron transport layer to the light emitting layer is easy, and the charge balance in the light emitting layer is increased. (Low driving voltage, high efficiency and lifetime) seems to be derived.

[Table 5]

The above description is merely illustrative 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 intended to explain, not limit, the present invention, and the spirit and scope of the present invention are not limited by these embodiments. The protection scope of the present invention should be construed according to the following claims, and all techniques within the scope equivalent thereto should be construed as being included in the scope of the present invention.

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

Claims (11)

A compound represented by Formula 1 below:
<Formula 1>

In Formula 1,
Ring A is an aromatic ring group of C ₆ to C ₁₄ ,
X is O, S or C(R')(R");
R ¹ to R ³ are each independently hydrogen; heavy hydrogen; halogen; C ₆ ~ C ₃₀ aryl group; fluorenyl group; A C ₂ ~C ₃₀ heterocyclic group containing at least one heteroatom selected from O, N, S, Si, and P; C ₃ ~ C ₃₀ aliphatic ring group; And it is selected from the group consisting of -L'-N(R _a )(R _b ), except when adjacent R ¹ or adjacent R ² bond to each other to form a ring, and adjacent R ³ mutually connected to form an aromatic ring of C ₆ ,
m is an integer from 0 to 8, n is an integer from 0 to 4, l is an integer from 0 to 2,
Wherein L is a single bond; C ₆ ~ C ₃₀ arylene group; Fluorenylene group; And it is selected from the group consisting of a C ₂ ~ C ₃₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P,
Ar ₁ is a C ₆ ~ C ₃₀ aryl group; fluorenyl group; A C ₂ ~C ₃₀ heterocyclic group containing at least one heteroatom selected from O, N, S, Si, and P; And -L'-N (R _a ) (R _b ) It is selected from the group consisting of,
o1, o2 and o3 are integers of 0 or 1, respectively, and m+n+l+o1+o2+o3 is an integer of 1 or greater;
When o1+o2+o3 is 0, at least one of R ¹ to R ³ is a C ₆ to C ₃₀ aryl group; fluorenyl group; A C ₂ ~C ₃₀ heterocyclic group containing at least one heteroatom selected from O, N, S, Si, and P; And -L'-N (R _a ) (R _b ) It is selected from the group consisting of,
Wherein R' and R" are each independently a C ₆ ~ C ₃₀ aryl group or a C ₁ ~ C ₁₀ alkyl group,
Wherein L' is a single bond or a C ₆ ~ C ₃₀ arylene group,
Wherein R _a and R _b are each independently a C ₆ ~ C ₃₀ aryl group,
The R ¹ to R ³ , L, Ar ₁ , R', R", L', R _a , R _b , and C ₆ aromatic rings formed by connecting adjacent R ³ groups are deuterium; halogen; cyano groups; Nitro group; C ₁ -C ₂₀ alkyl group; C ₂ -C ₂₀ alkenyl group; C ₆ -C ₂₀ aryl group; C ₆ -C ₂₀ aryl group substituted with deuterium; Fluorenyl group; O, N, A C ₂ -C ₂₀ heterocyclic group containing at least one heteroatom selected from the group consisting of S, Si and P; and a C ₃ -C ₂₀ cycloalkyl group, which may be further substituted with one or more substituents selected from the group consisting of have. According to claim 1,
A compound characterized in that Formula 1 is represented by one of the following Formulas 2 to 5:
<Formula 2><Formula3>

<Formula 4><Formula5>

In Formulas 2 to 5, X, R ¹ to R ³ , L and Ar ₁ are as defined in claim 1,
In Formula 2, l is 0 or 1, m and n are as defined in claim 1,
In Formula 3, m is an integer from 0 to 3, l and n are as defined in claim 1,
In Formula 4, n is an integer from 0 to 3, l and m are as defined in claim 1,
In Formula 5, l is 0 or 1, and m and n are each an integer of 0 to 3. According to claim 1,
A compound characterized in that at least one of R ¹ to R ³ is represented by the following formula A-1 or A-2:
<Formula A-1><FormulaA-2>

In the above formulas A-1 and A-2,
Q ¹ to Q ⁹ are each independently N or C (R ^e ),
R ^e is hydrogen; heavy hydrogen; halogen; cyano group; C ₁ -C ₂₀ Alkyl group; C ₆ -C ₂₀ aryl group; A deuterium-substituted C ₆ -C ₂₀ aryl group; fluorenyl group; A C ₂ -C ₂₀ heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P; And C ₃ -C ₂₀ It is selected from the group consisting of a cycloalkyl group,
Z is selected from the group represented by the formula below,

In the above formula of Z, * is a site bonded to a ring containing Q ¹ to Q ⁴ ,
V are independently of each other N or C(R ^h );
W ¹ and W ² are each independently a single bond, -NL ¹ -Ar ¹ , S, O or C(R ^f )(R ^g );
L ¹ is a single bond; C ₆ ~ C ₂₀ arylene group; Fluorenylene group; And it is selected from the group consisting of a C ₂ ~C ₂₀ heterocycle containing at least one heteroatom of O, N, S, Si and P,
Ar ¹ , R ^f , R ^g and R ^h are each independently a C ₆ -C ₂₀ aryl group; A deuterium-substituted C ₆ -C ₂₀ aryl group; fluorenyl group; A C ₂ -C ₂₀ heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P; And it is selected from the group consisting of a C ₃ -C ₂₀ cycloalkyl group, and R ^f and R ^g may bond to each other to form a ring. According to claim 1,
A compound, characterized in that the compound represented by Formula 1 is one of the following compounds:

. In the organic electric element including a first electrode, a second electrode, and an organic material layer formed between the first electrode and the second electrode,
An organic electric device, wherein the organic material layer comprises the compound of claim 1. According to claim 5,
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. According to claim 6,
The organic electric device, characterized in that the light emitting layer comprises the compound of claim 1. According to claim 5,
The organic layer is formed by a spin coating process, a nozzle printing process, an inkjet printing process, a slot coating process, a dip coating process, or a roll-to-roll process. According to claim 5,
The organic electric device further comprises a capping layer formed on one surface opposite to the organic material layer among both surfaces of the first electrode or both surfaces of the second electrode. A display device comprising the organic electric element of claim 5; and
An electronic device comprising a controller for driving the display device. According to claim 10,
The electronic device, characterized in that the organic electric device is selected from the group consisting of organic light emitting devices, organic solar cells, organic photoreceptors, organic transistors, devices for monochromatic lighting and devices for quantum dot displays.

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