KR102472915B1 - 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 materials can be classified into high molecular weight and low molecular weight according to molecular weight, and can be classified into fluorescent materials derived from singlet excited states of electrons and phosphorescent materials derived from triplet excited states of electrons according to light emitting mechanisms. have. 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 view of an organic electroluminescent device according to an embodiment of 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 bonded 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 indicating the hydrogen bonded to the carbon forming the benzene ring. is omitted.

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.

Ring A is a C ₆ ~ C ₂₀ aromatic ring, preferably a C ₆ ~ C ₁₈ aromatic ring, and may be, for example, benzene, naphthalene, phenanthrene, triphenylene, and the like.

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

When L ¹ 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 ¹ 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, quinazoline, and quinoxaline. , phthalazine, benzoquinazoline, dibenzoquinazoline, dibenzothiophene, dibenzofuran, carbazole, benzonaphthothiophene, benzothienopyrimidine, benzothienopyridine, benzofuropyrimidine , naphthopuropyrimidine, phenoxatine, 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; a thiol group unsubstituted or substituted with a C ₁ -C ₂₀ alkyl group or a C ₆ -C ₂₀ aryl group; And -L'-N (R _a ) (R _b ); may be selected from the group consisting of. Here, the "thiol group" may be expressed in the form of -SR, and when R is an alkyl group or an aryl group, it is referred to as 'a thiol group substituted with an alkyl group or an aryl group'.

When Ar ¹ is an aryl group, it is preferably a C ₆ -C ₃₀ aryl group, more preferably a C ₆ -C ₂₃ aryl group, still more preferably a C ₆ -C ₁₈ aryl group such as phenyl, naphtha ethyl, biphenyl, anthracene, phenanthrene, pyrene, triphenylene, terphenyl, dimethylindenophenanthrene, 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 ₁₈ heterocyclic group, such as pyridine, pyrimidine, triazine, quinazoline, and quinoxaline. , phthalazine, benzoquinazoline, dibenzoquinazoline, dibenzothiophene, dibenzofuran, carbazole, phenylcarbazole, benzonaphthothiophene, benzonaphthofuran, benzothienopyrimidine, benzothione enopyridine, benzofuropyrimidine, naphthofuropyrimidine, phenoxatine, benzimidazole, phenolbenzimidazole, indenoquinazoline, dihydroimidazopyridine, pyrimidoindole, pyrazine, and the like.

n is an integer of 1-2.

R ¹ to R ⁵ are each independently hydrogen; heavy hydrogen; halogen; cyano group; nitro group; 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 is selected from the group consisting of, adjacent groups may be bonded to each other to form a ring, wherein the ring is a C ₆ ~ C ₆₀ aromatic ring; A C ₂ ~C ₆₀ heterocycle containing at least one heteroatom selected from O, N, S, Si, and P; C ₃ ~ C ₆₀ aliphatic ring; and combinations thereof.

When R ¹ to R ⁵ are aryl groups, they are preferably C ₆ -C ₃₀ aryl groups, more preferably C ₆ -C ₁₂ aryl groups, such as phenyl, naphthyl, and biphenyl. When R ¹ to R ⁵ are heterocyclic groups, they are preferably C ₂ to C ₃₀ heterocyclic groups, more preferably C ₂ to C ₉ heterocyclic groups, still more preferably C ₂ to C ₅ heterocyclic groups. groups such as pyridine, triazine, quinoline, quinazoline, and the like.

When adjacent R ¹ and R ² , adjacent R ² and R ³ , adjacent R ³ and R ⁴ , or adjacent R ⁵ are bonded to each other to form an aromatic ring, preferably C ₆ to C ₃₀ aromatic A ring, more preferably a C ₆ ~ C ₁₄ aromatic ring, for example, a ring of benzene, naphthalene, phenanthrene, or the like may be formed.

m is an integer of 0 to 2, and when m is 2, each R ⁵ may be the same as or different from each other.

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

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

Each of the A rings, R ¹ to R ⁵ , Ar ¹ , L ¹ , L', R _a , R _b , and rings formed by bonding adjacent groups to each other includes 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; 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; C ₈ -C ₂₀ arylalkenyl group; And it may be further substituted with one or more substituents selected from the group consisting of combinations thereof.

Preferably, the compound represented by Formula 1 may be represented by one of Formulas 2 to 7 below.

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

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

In Formulas 2 to 7, ring A, L ¹ , Ar ¹ , R ¹ to R ⁵ are as defined in Formula 1, and m' is an integer of 0 to 2.

Preferably, Ar ¹ may be represented by Formula A-1 or A-2 below.

<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 ), and 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 above chemical formula of Z, * is a site bonded to a ring containing Q ¹ to Q ⁴ .

V is each independently N or C(R ^h ), and 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 compound 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 supplement, an electron transport layer, and an electron injection layer, and preferably, the compound 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 the compound represented by Formula 1 and an example of manufacturing an organic electric device according to the present invention will be described in detail with reference to examples, but the present invention is not limited to the following examples.

synthesis example

Compounds (final products) according to the present invention are synthesized by reacting Core and Sub as shown in Scheme 1 below, but are not limited thereto.

<Scheme 1> (where Hal is Br or Cl)

Core's synthesis example

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

<Scheme 2>

1. Core 1 synthesis example

Core 1 may be synthesized by the reaction pathway of Scheme 2-1 below.

<Scheme 2-1>

(1) Synthesis of SM-3-1

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

(2) Synthesis of SM-5-1

In a round bottom flask, SM-3-1 (1 equiv.), 2-chloroaniline (1.5 equiv.), Pd(OAc) ₂ (0.03 equiv.), P(t-Bu) ₃ (0.08 equiv.), NaO (t-Bu) (3.0 equivalent), toluene was added and stirred, and the reaction proceeded at 90°C. When the reaction is complete, the temperature is lowered to room temperature, extracted with ethyl acetate and water, and the organic layer is dried over Na ₂ SO ₄ and concentrated. Thereafter, the concentrate was passed through a silica gel column and recrystallized to obtain SM-5-1. (Yield: 70%)

(3) Synthesis of Core 1

SM-5-1 (1 equivalent), Pd(OAc) ₂ (0.03 equivalent), P(t-Bu) ₃ HBF ₄ (0.1 equivalent), K ₂ CO ₃ (3.0 equivalent), and DMA were added to a round bottom flask. After stirring, the reaction proceeds at 150 to 180°C. When the reaction is complete, the temperature is lowered to room temperature, the reactant is slowly put into ice water, stirred, and the precipitated solid is filtered. After dissolving the filtered solid in toluene, filtering using a silica filter, recrystallization and purification were performed to obtain Core 1. (Yield: 67%)

2. Core 4 synthesis example

Core 4 may be synthesized by the reaction pathway of Scheme 2-2 below.

<Scheme 2-2>

(1) Synthesis of SM-3-2

Add 1-bromo-2-aminonaphthalene (SM-1-2) (1 equiv.), CuI (0.2 equiv.), 1,10-phenanthroline (0.4 equiv.), and Cs ₂ CO ₃ (3 equiv.) to a round bottom flask and add xylene. After stirring at room temperature, 2-iodo-3-chloropyridine (SM-2-1) (1.2 equivalent) was added and the reaction proceeded at 120°C. When the reaction is complete, the temperature is lowered to room temperature, extracted with ethyl acetate and water, and the organic layer is dried over Na ₂ SO ₄ and concentrated. Thereafter, the concentrate was passed through a silica gel column and recrystallized to obtain SM-3-2. (Yield: 62%)

(2) Synthesis of SM-5-2

In a round bottom flask, SM-3-2 (1 equiv.), 2-chloro-1-aminonaphthalene (1.5 equiv.), Pd(OAc) ₂ (0.03 equiv.), P(t-Bu) ₃ (0.08 equiv.), NaO( t-Bu) (3.0 equivalent) and toluene were added and stirred, and the reaction proceeded at 90°C. When the reaction is complete, the temperature is lowered to room temperature, extracted with ethyl acetate and water, and the organic layer is dried over Na ₂ SO ₄ and concentrated. Thereafter, the concentrate was passed through a silica gel column and recrystallized to obtain SM-5-2. (Yield: 68%)

(3) Synthesis of Core 4

SM-5-2 (1 equivalent), Pd(OAc) ₂ (0.03 equivalent), P(t-Bu) ₃ HBF ₄ (0.1 equivalent), K ₂ CO ₃ (3.0 equivalent), DMA were added to a round bottom flask and stirred. After that, the reaction proceeds at 150 ~ 180 ℃. When the reaction is completed, the temperature is lowered to room temperature, the reactant is slowly put into ice water, stirred, and the precipitated solid is filtered out. The filtered solid was dissolved in o-Dichlorobenzene, filtered using a silica filter, recrystallized and purified to obtain Core 4. (Yield: 80%)

The compounds belonging to the Core are as follows, but are not limited thereto, and the FD-MS values of the following compounds are shown in Table 1 below.

[Table 1]

Sub's synthesis example

A compound belonging to Sub of Reaction Scheme 1 may be synthesized by Reaction Scheme 3 below, but is not limited thereto.

<Scheme 3> (Hal ¹ = I, Br or Cl, and Hal ² = Br or Cl)

1. of Sub 29 synthesis example

In a round bottom flask, Sub 29-1 (1.0 equiv.), 4,4,5,5-tetramethyl-2-phenyl-1,3,2-dioxaborolane (1.3 equiv.), Pd(PPh ₃ ) ₄ (0.03 equiv.), After adding K ₂ CO ₃ (3 equivalents), THF/H ₂ O was added at a ratio of 2:1, and a reflux reaction was performed at 70°C. When the reaction is complete, the temperature is lowered to room temperature, extracted with CH ₂ Cl ₂ and water, and the organic layer is dried over MgSO ₄ and concentrated. Thereafter, the concentrate was passed through a silica gel column and recrystallized to obtain Sub 29. (Yield: 80%)

2. Sub 44 synthesis example

In a round bottom flask, Sub 44-1 (1.0 equiv.), 4,4,5,5-tetramethyl-2-phenyl-1,3,2-dioxaborolane (1.3 equiv.), Pd(PPh ₃ ) ₄ (0.03 equiv.), After adding K ₂ CO ₃ (3 equivalents), THF/H ₂ O was added at a ratio of 2:1, and a reflux reaction was performed at 70°C. When the reaction is complete, the temperature is lowered to room temperature, extracted with CH ₂ Cl ₂ and water, and the organic layer is dried over MgSO ₄ and concentrated. Thereafter, the concentrate was passed through a silica gel column and recrystallized to obtain Sub 44. (Yield: 85%)

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

[Table 2]

of the final compound synthesis example

of 1-6 synthesis example

In a round bottom flask, Core 1 (1.0 equiv.), Sub 29 (1.1 equiv.), Pd ₂ (dba) ₃ (0.03 equiv.), P(t-Bu) ₃ (0.08 equiv.), NaO (t-Bu) (3 equiv.) ), toluene is added and the reaction proceeds at 90~110℃. When the reaction is complete, the temperature is lowered to room temperature, water is added and stirred, and the precipitated solid is filtered. After filtering, the solid is boiled and dissolved in o-DCB, and filtered using a silica filter. Thereafter, the solvent was removed and recrystallized to obtain Compound 1-6. (Yield: 80%)

of 1-10 synthesis example

Core 1 (1.0 equivalent), Sub 65 (1.1 equivalent), Pd ₂ (dba) ₃ (0.03 equivalent), P(t-Bu) ₃ (0.08 equivalent), NaO (t-Bu) (3 equivalent), Toluene Compound 1-10 was obtained in the same manner as the synthesis method of Compound 1-6. (Yield: 82%)

1-65 synthesis example

Core 10 (1.0 equivalent), Sub 40 (1.1 equivalent), Pd ₂ (dba) ₃ (0.03 equivalent), P(t-Bu) ₃ (0.08 equivalent), NaO (t-Bu) (3 equivalent), Toluene Compound 1-65 was obtained in the same manner as the synthesis method of Compound 1-6. (Yield: 75%)

1-72 synthesis example

Core 14 (1.0 equivalent), Sub 15 (1.1 equivalent), Pd ₂ (dba) ₃ (0.03 equivalent), P(t-Bu) ₃ (0.08 equivalent), NaO (t-Bu) (3 equivalent), Toluene Compound 1-72 was obtained in the same manner as in the synthesis method of Compound 1-6. (Yield: 75%)

1-82 synthesis example

Core 15 (1.0 equivalent), Sub 78 (1.1 equivalent), Pd ₂ (dba) ₃ (0.03 equivalent), P(t-Bu) ₃ (0.08 equivalent), NaO (t-Bu) (3 equivalent), Toluene Compound 1-82 was obtained in the same manner as in the synthesis method of Compound 1-6. (Yield: 80%)

1-90 synthesis example

Core 17 (1.0 equivalent), Sub 59 (1.1 equivalent), Pd ₂ (dba) ₃ (0.03 equivalent), P(t-Bu) ₃ (0.08 equivalent), NaO (t-Bu) (3 equivalent), Toluene Compound 1-90 was obtained in the same manner as the synthesis method of Compound 1-6. (Yield: 83%)

of 1-112 synthesis example

Core 19 (1.0 equivalent), Sub 59 (1.1 equivalent), Pd ₂ (dba) ₃ (0.03 equivalent), P(t-Bu) ₃ (0.08 equivalent), NaO (t-Bu) (3 equivalent), Toluene Compound 1-112 was obtained in the same manner as the synthesis method of Compound 1-6. (Yield: 69%)

The FD-MS values of Compound 1-1 to Compound 1-117 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 1] Red organic light emitting 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. Thereafter, Compound 1-1 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 30 nm thick light emitting layer was deposited by doping the dopant so that the weight ratio was 95: 5. Next, (1,1'-biphenyl-4-olato)bis(2-methyl-8- A hole blocking layer is formed by vacuum depositing quinolinolato)aluminum (hereinafter abbreviated as "BAlq") to a thickness of 10 nm, and tris(8-quinolinol)aluminum (hereinafter abbreviated as Alq ₃₎ is formed on the hole blocking layer. ) was formed to a thickness of 40 nm to form an electron transport layer After that, LiF was deposited to a thickness of 0.2 nm on the electron transport layer to form an electron injection layer, and Al was deposited on the electron injection layer to a thickness of 150 nm. A cathode was formed.

[ Example 2] to [ Example 38]

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 1-1 as the host material of the light emitting layer.

[ comparative example 1] and [ comparative example 2]

An organic light emitting device was manufactured in the same manner as in Example 1, except that Comparative Compound 1 and Comparative Compound 2 were used instead of Compound 1-1 of the present invention as the host material of the light emitting layer.

<Comparative compound 1> <Comparative compound 2>

By applying a forward bias DC voltage to the organic electroluminescent devices manufactured by Examples 1 to 38, Comparative Example 1, and Comparative Example 2 of the present invention, electroluminescence (EL) with PR-650 of Photoresearch Co., Ltd. The characteristics were measured, and 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, when the compound according to one embodiment of the present invention is used as a phosphorescent host material of the light emitting layer, compared to the case of using Comparative Compound 1 or Comparative Compound 2, the device characteristics of the organic electroluminescent device This has been markedly improved.

More specifically, compared to CBP (Comparative Compound 1), which is generally used as a host material for the light emitting layer, the device using the compound of Comparative Compound 2 having a skeleton similar to that of the compound of the present invention as a host has excellent results in terms of driving voltage, efficiency and lifespan. In the case of using the compound of the present invention including at least five rings in which at least one benzene was fused at a specific position of Comparative Compound 2, the characteristics of the device were the best.

As one more benzene is fused to a specific position, the physical properties of the compound, such as the energy level and T1 level of the compound, are significantly different from those of the comparative compound. It is a red host material to have more suitable properties. Therefore, when a device is manufactured by depositing a compound, it is suggested that the properties of the device can be changed by changing the physical properties of the compound acting as a major factor (eg, energy balance) in device performance.

In addition, since the compound of the present invention has a relatively higher Tg value than Comparative Compound 1 and Comparative Compound 2, the thermal stability of the compound of the present invention is improved. Therefore, it seems that the efficiency and lifetime of the organic light emitting device using the compound of the present invention as a red host material are improved.

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 (10)

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

In Formula 1,
A ring is a C ₆ ~ C ₂₀ aromatic ring group,
L ¹ is a single bond; C ₆ ~ C ₆₀ arylene group; Fluorenylene group; C ₃ ~ C ₆₀ aliphatic ring group; A C ₂ ~C ₆₀ heterocyclic group containing at least one heteroatom selected from O, N, S, Si, and P; And it is selected from the group consisting of combinations thereof,
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; a thiol group unsubstituted or substituted with a C ₁ -C ₂₀ alkyl group or a C ₆ -C ₂₀ aryl group; And -L'-N (R _a ) (R _b ); is selected from the group consisting of,
n is an integer from 1 to 2;
R ¹ to R ⁵ are each independently hydrogen; heavy hydrogen; halogen; cyano group; nitro group; 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 is selected from the group consisting of, adjacent groups may be bonded to each other to form a ring, wherein the ring is a C ₆ ~ C ₆₀ aromatic ring 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 selected from combinations thereof,
m is an integer from 0 to 2, and when m is 2, each R ⁵ is the same as or different from each other;
L' is a single bond; C ₆ ~ C ₆₀ arylene group; Fluorenylene group; C ₃ ~ C ₆₀ aliphatic ring group; A C ₂ ~C ₆₀ heterocyclic group containing at least one heteroatom selected from O, N, S, Si, and P; And it is selected from the group consisting of combinations thereof,
Wherein R _a and R _b are each independently a C ₆ ~ C ₆₀ aryl group; fluorenyl group; C ₃ ~ C ₆₀ aliphatic ring group; A C ₂ ~C ₆₀ heterocyclic group containing at least one heteroatom selected from O, N, S, Si, and P; And it is selected from the group consisting of combinations thereof,
Each of the A rings, R ¹ to R ⁵ , Ar ¹ , L ¹ , L', R _a , R _b , and rings formed by bonding adjacent groups to each other includes 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; 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; C ₈ -C ₂₀ arylalkenyl group; And it may be further substituted with one or more substituents selected from the group consisting of combinations thereof,
However, compounds represented by the following formula (3) in the above formula (1) are excluded:
<Formula 3>

In Formula 3, ring A, L ¹ , Ar ¹ , R ¹ to R ⁵ are as defined in claim 1, and m' is an integer of 0 to 2. According to claim 1,
The compound represented by Formula 1 is a compound characterized by being represented by one of Formulas 2 and 4 to 7 below:
<Formula 2><Formula4>

<Formula 5><Formula6><Formula7>

In Formula 2 and Formula 4 to Formula 7, ring A, L ¹ , Ar ¹ , R ¹ to R ⁵ are as defined in claim 1, and m' is an integer of 0 to 2. According to claim 1,
Ar ¹ is a compound characterized in that 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; 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 C ₈ -C ₂₀ It is selected from the group consisting of an arylalkenyl 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 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; is 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. 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,
The organic material layer is an organic electric device, characterized in that it comprises a compound represented by the formula (1) 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 compound is included in the light emitting layer. 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. 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 9,
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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