KR102149449B1 - Novel organic compounds for organic light-emitting diode and organic light-emitting diode including the same - Google Patents

Abstract

상기 화학식 A에서 R₁ 내지 R₅, k 내지 o, L은 발명의 상세한 설명에 기재된 바와 같다. The present invention relates to an organic light-emitting compound represented by the following [Chemical Formula A] and an organic light-emitting device including the same.
[Formula A]

In Formula A, R ₁ to R ₅ , k to o, and L are as described in the detailed description of the invention.

Description

Compound for organic light-emitting device and organic light-emitting device including the same {Novel organic compounds for organic light-emitting diode and organic light-emitting diode including the same}

The present invention relates to a compound for an organic light-emitting device capable of implementing an organic light-emitting device with a low driving voltage, and an organic light-emitting device including the same, and more particularly, when used as a fluorescent host, excellent device characteristics are achieved through a low driving voltage. It relates to a compound for an organic light-emitting device that can be implemented and an organic light-emitting device including the same.

An organic light emitting diode (OLED) is a display using a self-luminous phenomenon, and has a large viewing angle, can be light and thin compared to a liquid crystal display, and has advantages such as a fast response speed. ) Application to display or lighting is expected.

In general, the organic light emission phenomenon refers to a phenomenon in which electrical energy is converted into light energy using an organic material. An organic light emitting device using the organic light emitting phenomenon has a structure including an anode, a cathode, and an organic material layer therebetween. Here, the organic material layer is often made of a multi-layered structure composed of different materials in order to increase the efficiency and stability of the organic light-emitting device.For example, it may be formed of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like. In the structure of such an organic light-emitting device, when a voltage is applied between the two electrodes, holes are injected from the anode and electrons from the cathode are injected into the organic material layer, and excitons are formed when the injected holes and electrons meet. It glows when it falls back to the ground. These organic light-emitting devices are known to have characteristics such as self-luminescence, high luminance, high efficiency, low driving voltage, wide viewing angle, high contrast, and high-speed response.

Materials used as the organic material layer in the organic light-emitting device can be classified into light-emitting materials and charge transport materials, such as hole injection materials, hole transport materials, electron transport materials, and electron injection materials, according to their functions. The light-emitting material may be classified into a high-molecular-type and a low-molecular-type according to its molecular weight, and may be classified into a fluorescent material derived from the singlet excited state of the electron and a phosphorescent material derived from the triplet excited state of the electron according to the light emitting mechanism. . In addition, the light-emitting material may be classified into blue, green, and red light-emitting materials and yellow and orange light-emitting materials necessary for realizing a better natural color according to the light-emitting color.

On the other hand, when only one material is used as a light-emitting material, the maximum light-emitting wavelength shifts to a long wavelength due to the interaction between molecules, and the color purity decreases, or the efficiency of the device decreases due to the light-emitting attenuation effect. In order to increase the luminous efficiency through transition, a host-dopant system may be used as a light emitting material.

The principle is that when a small amount of a dopant having an energy band gap smaller than that of the host forming the light emitting layer is mixed in the light emitting layer, excitons generated in the light emitting layer are transported to the dopant to emit light with high efficiency. At this time, since the wavelength of the host moves to the wavelength of the dopant, light having a desired wavelength can be obtained according to the type of dopant used.

As a prior art for a host compound among such light emitting layers, Patent Publication No. 10-0910150 (2009.08.03) relates to an organic light emitting device comprising a compound in which a heterocyclic substituent is bonded to the terminal of an anthracene structure in the light emitting medium layer. In Japanese Patent Publication No. 5608978 (October 22, 2014), a technology related to an organic light-emitting device comprising an anthracene derivative in which a substituent of a dibenzofuran structure is bonded to the terminal of an anthracene structure in the light emitting medium layer is described. have.

However, despite the production of various kinds of compounds for use in the light emitting medium layer, including the prior art, the necessity of developing an organic material layer material for an organic light emitting device capable of driving an organic light emitting device at a lower voltage has continued. It is being demanded.

Registered Patent Publication No. 10-0910150 (2009.08.03)

Japanese Registered Patent Publication No. 5608978 (2014.10.22)

Accordingly, the first technical problem to be achieved by the present invention is to provide a compound for an organic light-emitting device that can be used for an organic light-emitting layer and can be driven at a low voltage.

A second technical problem to be achieved by the present invention is to provide an organic light-emitting device including the compound.

The present invention provides an organic light-emitting compound represented by the following [Chemical Formula A] in order to achieve the first technical problem.

[Formula A]

In the above [Formula A],

R ₁ to R ₅ are each the same or different, and independently of each other, hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted carbon number 2 to 30 alkynyl group, substituted or unsubstituted C 3 to C 30 cycloalkyl group, substituted or unsubstituted C 5 to C 30 cycloalkenyl group, substituted or unsubstituted C 1 to C 30 alkoxy group, substituted or unsubstituted A substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkyl thioxy group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthioxy group having 5 to 30 carbon atoms, a substituted or unsubstituted alkyl having 1 to 30 carbon atoms An amine group, a substituted or unsubstituted arylamine group having 5 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted hetero atom having O, N or S as a hetero atom and having 2 to 50 carbon atoms Aryl group, cyano group, nitro group, halogen group, substituted or unsubstituted silyl group having 1 to 30 carbon atoms, substituted or unsubstituted germanium group having 1 to 30 carbon atoms, substituted or unsubstituted boron group having 1 to 30 carbon atoms , Substituted or unsubstituted aluminum group having 1 to 30 carbon atoms, carbonyl group, phosphoryl group, amino group, thiol group, hydroxy group, selenium group, tellurium group, amide group, ether group and ester group,

Hydrogen is bonded to carbon of the aromatic ring to which the substituents of R ₁ to R ₅ are not bonded,

The linking group L is a single bond, a substituted or unsubstituted arylene group having 6 to 60 carbon atoms;

k is an integer from 1 to 5,

l to n are each the same or different from each other, and are independently an integer of 1 to 4,

o is an integer from 1 to 3,

When each of the k to o is 2 or more, each of R ₁ to R ₅ is the same as or different from each other,

'***' of X may be a bonding site that binds to the linker L.

In addition, the present invention in order to achieve the second object, the first electrode; A second electrode facing the first electrode; And an organic layer interposed between the first electrode and the second electrode, wherein the organic layer includes at least one organic light-emitting compound of the present invention.

According to the present invention, the organic light-emitting compound represented by [Chemical Formula A] has excellent characteristics that enable the driving of the organic light-emitting device at a lower voltage than the organic light-emitting compound according to the prior art.

1 is a schematic diagram of an organic light-emitting device according to an embodiment of the present invention.

Hereinafter, the present invention will be described in more detail.

The present invention provides a compound represented by the following [Chemical Formula A] as a novel aromatic organic light emitting compound.

[Formula A]

R ₁ to R ₅ are each the same or different, and independently of each other, hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted carbon number 2 to 30 alkynyl group, substituted or unsubstituted C 3 to C 30 cycloalkyl group, substituted or unsubstituted C 5 to C 30 cycloalkenyl group, substituted or unsubstituted C 1 to C 30 alkoxy group, substituted or unsubstituted A substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkyl thioxy group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthioxy group having 5 to 30 carbon atoms, a substituted or unsubstituted alkyl having 1 to 30 carbon atoms An amine group, a substituted or unsubstituted arylamine group having 5 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted hetero atom having O, N or S as a hetero atom and having 2 to 50 carbon atoms Aryl group, cyano group, nitro group, halogen group, substituted or unsubstituted silyl group having 1 to 30 carbon atoms, substituted or unsubstituted germanium group having 1 to 30 carbon atoms, substituted or unsubstituted boron group having 1 to 30 carbon atoms , A substituted or unsubstituted C 1 to C 30 aluminum group, a carbonyl group, a phosphoryl group, an amino group, a thiol group, a hydroxy group, a selenium group, a tellurium group, an amide group, an ether group, and an ester group,

Hydrogen is bonded to carbon of the aromatic ring to which the substituents of R ₁ to R ₅ are not bonded,

The linking group L is a single bond, a substituted or unsubstituted arylene group having 6 to 60 carbon atoms;

k is an integer from 1 to 5,

l to n are each the same or different from each other, and are independently an integer of 1 to 4,

o is an integer from 1 to 3,

When each of the k to o is 2 or more, each of R1 to R5 is the same as or different from each other,

'***' of X is a binding site that binds to the connector L,

'Substitution' in'substituted or unsubstituted' in [Chemical Formula A] is deuterium, cyano group, halogen group, hydroxy group, nitro group, alkyl group having 1 to 24 carbon atoms, halogenated alkyl group having 1 to 24 carbon atoms, carbon number 1 to 24 alkenyl group, C 1 to C 24 alkynyl group, C 1 to C 24 heteroalkyl group, C 6 to 24 aryl group, C 6 to C 24 arylalkyl group, C 2 to C 24 heteroaryl group or C 2 To 24 heteroarylalkyl group, C 1 to C 24 alkoxy group, C 1 to C 24 alkylamino group, C 1 to C 24 arylamino group, C 1 to C 24 hetero arylamino group, C 1 to C 24 alkylsilyl group, C carbon number It means substituted with one or more substituents selected from the group consisting of an arylsilyl group of 1 to 24 and an aryloxy group of 1 to 24 carbon atoms.

In addition, considering the range of the alkyl group or aryl group in the "substituted or unsubstituted alkyl group having 1 to 24 carbon atoms" and "substituted or unsubstituted aryl group having 6 to 24 carbon atoms", the carbon number is 1 to 24 The range of the number of carbon atoms of the alkyl group and the aryl group having 6 to 24 carbon atoms, respectively, means the total number of carbon atoms constituting the alkyl moiety or the aryl moiety when the substituent is viewed as unsubstituted without considering the substituted moiety. For example, a phenyl group substituted with a butyl group at the para position should be considered to correspond to an aryl group having 6 carbon atoms substituted with a butyl group having 4 carbon atoms.

The aryl group as a substituent used in the compound of the present invention means an aromatic system consisting of a hydrocarbon containing one or more rings, and when the aryl group has a substituent, it is fused with each other with neighboring substituents to further form a ring. I can.

Specific examples of the aryl group include a phenyl group, o-biphenyl group, m-biphenyl group, p-biphenyl group, o-terphenyl group, m-terphenyl group, p-terphenyl group, naphthyl group, anthryl group, phenanthryl group, Aromatic groups such as pyrenyl group, indenyl, fluorenyl group, tetrahydronaphthyl group, peryleneyl, chrysenyl, naphthacenyl, fluoranthenyl, etc., and at least one hydrogen atom in the aryl group is a deuterium atom, a halogen atom , Hydroxy group, nitro group, cyano group, silyl group, amino group (-NH ₂ , -NH(R), -N(R')(R''), R'and R" are independently of each other having 1 to 10 carbon atoms Alkyl group, in this case referred to as "alkylamino group"), amidino group, hydrazine group, hydrazone group, carboxyl group, sulfonic acid group, phosphoric acid group, alkyl group having 1 to 24 carbon atoms, halogenated alkyl group having 1 to 24 carbon atoms, 1 to 24 carbon atoms Alkenyl group, C1-C24 alkynyl group, C1-C24 heteroalkyl group, C6-C24 aryl group, C6-C24 arylalkyl group, C2-C24 heteroaryl group, or C2-C24 It may be substituted with a heteroarylalkyl group.

The heteroaryl group as a substituent used in the compound of the present invention refers to a cyclic aromatic system having 2 to 24 carbon atoms including 1, 2 or 3 hetero atoms selected from N, O, P or S, and the remaining ring atoms are carbon, The rings may be fused to form a ring. And at least one hydrogen atom in the heteroaryl group may be substituted with the same substituent as in the case of the aryl group.

Specific examples of the alkyl group as a substituent used in the present invention include methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, pentyl, iso-amyl, hexyl, and the like, and at least one hydrogen atom in the alkyl group is The atom may be substituted with the same substituent as in the case of the aryl group.

Specific examples of the alkoxy group that is a substituent used in the compound of the present invention include methoxy, ethoxy, propoxy, isobutyloxy, sec-butyloxy, pentyloxy, iso-amyloxy, hexyloxy, and the like, At least one hydrogen atom in the alkoxy group may be substituted with the same substituent as in the case of the aryl group.

Specific examples of the silyl group as a substituent used in the compound of the present invention include trimethylsilyl, triethylsilyl, triphenylsilyl, trimethoxysilyl, dimethoxyphenylsilyl, diphenylmethylsilyl, silyl, diphenylvinylsilyl, methylcyclo Butylsilyl, dimethylfurylsilyl, and the like. At least one hydrogen atom in the silyl group may be substituted with the same substituent as in the case of the aryl group.

In the present invention, the compound represented by Formula A has a linking group L bonded to the 9th position of the anthracene ring, as shown in Figure 1 below, as shown in Figure 1 below, 1 or 2 of either phenyl ring of a substituted or unsubstituted dibenzofuran. It is characterized in that it binds to the carbon atom at the first position.

[그림 1]

[Picture 1]

When the compound represented by Formula A is used as an emission layer of an organic light-emitting device, the resulting organic light-emitting device may exhibit a low driving voltage.

In the present invention, the compound represented by Formula A may be a single bond in which the linking group L is a single bond, or any one selected from [Structural Formula 1] or [Structural Formula 2] below.

[Structural Formula 1] [Structural Formula 2]

Here, in the linking group L, hydrogen or deuterium may be bonded to the carbon site of the aromatic ring.

For example, the linking group L may be a single bond or may have a structure represented by the following [L1] to [L6].

L1 L2 L3 L4 L5 L6

Here, the'-*' is a binding site that is bound to anthracene, and the'-**' is a binding site that is bound to X.

In addition, at least one of the substituents R ₁ to R ₅ in Formula A of the present invention may include deuterium.

As an example, the substituent R ₁ may be deuterium and k may be 5.

As an example, R ₂ and/or R ₃ may be deuterium, and l may be 2 or more, or m may be 2 or more.

As an example, R ₂ and R ₃ are deuterium at the same time, and l and m may be 2 or more.

In an embodiment, R ₄ and/or R ₅ may be deuterium, and n may be 2 or more, or o may be 2 or more.

In an embodiment, R ₄ and R ₅ are deuterium at the same time, and n and o may be 2 or more.

Hereinafter, as a representative structural formula of the organic light emitting compound of the present invention, any one compound selected from the group represented by the following [Chemical Formula 1] to [Chemical Formula 138] is illustrated, but the compounds according to the present invention are not limited thereto.

<Compound 1> <Compound 2> <Compound 3>

<화합물 4> <화합물 5> <화합물 6>

<Compound 4><Compound5><Compound6>

<Compound 7> <Compound 8> <Compound 9>

<Compound 10> <Compound 11> <Compound 12>

<Compound 13> <Compound 14> <Compound 15>

<Compound 16> <Compound 17> <Compound 18>

<Compound 19> <Compound 20> <Compound 21>

<Compound 22> <Compound 23> <Compound 24>

<Compound 25> <Compound 26> <Compound 27>

<Compound 28> <Compound 29> <Compound 30>

<Compound 31> <Compound 32> <Compound 33>

<Compound 34> <Compound 35> <Compound 36>

<Compound 37> <Compound 38> <Compound 39>

<Compound 40> <Compound 41> <Compound 42>

<Compound 43> <Compound 44> <Compound 45>

<Compound 46> <Compound 47> <Compound 48>

<Compound 49> <Compound 50> <Compound 51>

<Compound 52> <Compound 53> <Compound 54>

<Compound 55> <Compound 56> <Compound 57>

<Compound 58> <Compound 59> <Compound 60>

<Compound 61> <Compound 62> <Compound 63>

<Compound 64> <Compound 65> <Compound 66>

<Compound 67> <Compound 68> <Compound 69>

<Compound 70> <Compound 71> <Compound 72>

<Compound 73> <Compound 74> <Compound 75>

<Compound 76> <Compound 77> <Compound 78>

<Compound 79> <Compound 80> <Compound 81>

<Compound 82> <Compound 83> <Compound 84>

<Compound 85> <Compound 86> <Compound 87>

<Compound 88> <Compound 89> <Compound 90>

<Compound 91> <Compound 92> <Compound 93>

<Compound 94> <Compound 95> <Compound 96>

<Compound 97> <Compound 98> <Compound 99>

<Compound 100> <Compound 101> <Compound 102>

<Compound 103> <Compound 104> <Compound 105>

<Compound 106> <Compound 107> <Compound 108>

<Compound 109> <Compound 110> <Compound 111>

<Compound 112> <Compound 113> <Compound 114>

<Compound 115> <Compound 116> <Compound 117>

<Compound 118> <Compound 119> <Compound 120>

<Compound 121> <Compound 122> <Compound 123>

<Compound 124> <Compound 125> <Compound 126>

<Compound 127> <Compound 128> <Compound 129>

<Compound 130> <Compound 131> <Compound 132>

<Compound 133> <Compound 134> <Compound 135>

<Compound 136> <Compound 137> <Compound 138>

In addition, the present invention is a first electrode; A second electrode facing the first electrode; And an organic layer interposed between the first electrode and the second electrode, wherein the organic layer includes at least one kind of the organic light-emitting compound in the present invention.

In the present invention, "(organic layer) includes one or more compounds", "(organic layer) may include one compound belonging to the scope of the present invention or two or more different compounds belonging to the scope of the compound. It can be interpreted as".

In this case, the organic layer containing the compound of the present invention may include at least one of a hole injection layer, a hole transport layer, a functional layer having both a hole injection function and a hole transport function, a light emitting layer, an electron transport layer, and an electron injection layer.

In addition, according to the present invention, the organic layer interposed between the first electrode and the second electrode may be a light emitting layer. In this case, the light emitting layer is made of a host and a dopant, and the compound of Formula A may be used as a host.

In this case, specific examples of the dopant material used in the light emitting layer include a pyrene compound, a deuterium substituted pyrene compound, an arylamine, a deuterium substituted arylamine, a peryl compound, a deuterium substituted peryl compound, a pyrrole compound, Deuterium-substituted pyrrole-based compounds, hydrazone-based compounds, deuterium-substituted hydrazone-based compounds, carbazole-based compounds, deuterium-substituted carbazole-based compounds, stilbene-based compounds, deuterium-substituted stilbene-based compounds, starburst-based compounds, deuterium-substituted starburst Compounds, oxadiazole compounds, deuterium substituted oxadiazole compounds, coumarine, deuterium substituted coumarin, and the like, but the present invention is not limited thereto.

When the emission layer includes a host and a dopant, the content of the dopant may be generally selected in the range of about 0.01 to about 20 parts by weight based on about 100 parts by weight of the host, but is not limited thereto.

In addition, in the present invention, at least one layer selected from the hole injection layer, the hole transport layer, a functional layer having a hole injection function and a hole transport function at the same time, a light emitting layer, an electron transport layer, and an electron injection layer is formed by a single molecule deposition method or a solution process. Can be. Here, the deposition method refers to a method of forming a thin film by evaporating a material used as a material for forming each layer through heating in a vacuum or low pressure state to form a thin film, and the solution process is used to form the respective layers. It refers to a method of forming a thin film through a method such as inkjet printing, roll-to-roll coating, screen printing, spray coating, dip coating, spin coating, etc., by mixing a material used as a material for use with a solvent.

In addition, the organic light emitting device in the present invention includes a flat panel display device; Flexible display device; Monochrome or white flat lighting devices; And a single color or white flexible lighting device; may be used in any one device selected from.

As a specific example of the present invention, a hole transport layer (HTL) is additionally stacked between the anode and the organic light emitting layer, and an electron transport layer (ETL) is added between the cathode and the organic light emitting layer. Can be stacked with.

As the material of the hole transport layer, electron donating molecules having a small ionization potential are used, and diamine, triamine, or tetraamine derivatives mainly having triphenylamine as a basic skeleton are widely used. For example, N,N'-bis (3-Methylphenyl)-N,N'-diphenyl-[1,1-biphenyl]-4,4'-diamine (TPD) or N,N'-di(naphthalen-1-yl)-N,N '-Diphenylbenzidine (a-NPD) and the like can be used.

A hole injection layer (HIL) may be additionally laminated under the hole transport layer, and the hole injection layer material is also not particularly limited as long as it is commonly used in the art. For example, CuPc (copperphthalocyanine) or starburst amines TCTA (4,4',4"-tri(N-carbazolyl)triphenyl-amine), m-MTDATA(4,4',4"-tris-(3-methylphenylphenyl) amino)triphenylamine), etc. can be used.

In addition, as the electron transport layer material, for example, oxadiazole derivatives PBD, BMD, BND, or Alq ₃ may be used.

On the other hand, on the top of the electron transport layer, an electron injecting layer (EIL) that facilitates electron injection from the cathode and ultimately improves power efficiency may be further stacked. The material of the electron injection layer Also, as long as it is commonly used in the art, it may be used without particular limitation, and for example, materials such as LiF, NaCl, CsF, Li ₂ O, and BaO may be used.

Hereinafter, the organic light-emitting device of the present invention will be described with reference to FIG. 1.

1 is a cross-sectional view showing the structure of an organic light-emitting device of the present invention. The organic light emitting device according to the present invention includes an anode 20, a hole transport layer 40, an organic light emitting layer 50, an electron transport layer 60, and a cathode 80, and if necessary, a hole injection layer 30 and an electron The injection layer 70 may be further included, and in addition, it is possible to further form one or two intermediate layers.

Referring to FIG. 1, an organic light-emitting device of the present invention and a method of manufacturing the same are as follows. First, an anode 20 is formed by coating a material for an anode electrode on the substrate 10. Here, as the substrate 10, a substrate used in a conventional organic EL device is used, and an organic substrate or a transparent plastic substrate excellent in transparency, surface smoothness, ease of handling and waterproofness is preferable. In addition, as a material for the anode electrode, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO ₂ ), zinc oxide (ZnO), etc., which are transparent and have excellent conductivity, are used.

The hole injection layer 30 is formed by vacuum thermal evaporation or spin coating on the anode 20 electrode. Then, a hole transport layer material is vacuum thermally evaporated or spin coated on the hole injection layer 30 to form the hole transport layer 40.

Subsequently, an organic light-emitting layer 50 is stacked on the hole transport layer 40 and a hole blocking layer (not shown) is selectively formed on the organic light-emitting layer 50 by a vacuum deposition method or a spin coating method. can do. The hole blocking layer plays a role of preventing such a problem by using a material having a very low HOMO (Highest Occupied Molecular Orbital) level because when holes pass through the organic light emitting layer and flow into the cathode, the life and efficiency of the device are reduced. . In this case, the hole blocking material to be used is not particularly limited, but must have an electron transport capability and an ionization potential higher than that of a light-emitting compound, and representatively, BAlq, BCP, TPBI, and the like may be used.

After depositing the electron transport layer 60 on the hole blocking layer through a vacuum deposition method or a spin coating method, an electron injection layer 70 is formed, and a cathode-forming metal is vacuum-heated on the electron injection layer 70. The organic EL device is completed by vapor deposition to form the cathode 80 electrode. Here, the cathode-forming metal is lithium (Li), magnesium (Mg), aluminum (Al), aluminum-ridium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), and magnesium-silver ( Mg-Ag) or the like may be used, and in order to obtain a top light emitting device, a transmissive cathode using ITO or IZO may be used.

Further, according to a specific example of the present invention, it is preferable that the thickness of the emission layer is 50 to 2,000 Å, and the emission layer may be formed of a host and a dopant, and the compound of the present invention may be used as a host.

In this case, the dopant may be a compound represented by the following [Chemical Formula 1] or [Chemical Formula 2]. In this case, the emission layer may additionally include various dopant materials.

[Formula 1] [Formula 2]

In [Chemical Formula 1] and [Chemical Formula 2],

A is a substituted or unsubstituted aryl group having 5 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 50 carbon atoms having O, N or S as a hetero atom, a substituted or unsubstituted arylene group having 6 to 60 carbon atoms , It may be any one selected from a substituted or unsubstituted heteroarylene group having 3 to 50 carbon atoms having O, N or S as a hetero atom.

More specifically, A is a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, or a single bond, preferably anthracene, pyrene, phenanthrene, indenophenanthrene, chrysene, naphthacene, picene, triphenyl It may be any one of ene, perylene, and pentacene, and more specifically, A may be a substituent represented by any one of the following Formulas A1 to A10.

[Formula A1] [Formula A2] [Formula A3]

[Formula A4] [Formula A5] [Formula A6]

[Formula A7] [Formula A8] [Formula A9]

[Formula A10]

Wherein Z ₁ to Z ₂ in the [Chemical Formula A3] are hydrogen, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms, a substituted or unsubstituted carbon number 2 To 60 alkynyl group, substituted or unsubstituted C1-C60 alkoxy group, substituted or unsubstituted C1-C60 alkylthio group (alkylthio), substituted or unsubstituted C3-C60 cycloalkyl group, substituted Or an unsubstituted C6 to C60 aryl group, a substituted or unsubstituted C5 to C60 aryloxy group, a substituted or unsubstituted C5 to C60 arylthio group, a substituted or unsubstituted C2 to C60 Heteroaryl group, substituted or unsubstituted (alkyl) amino group having 1 to 60 carbon atoms, di(substituted or unsubstituted alkyl having 1 to 60 carbon atoms) amino group, or (substituted or unsubstituted aryl having 6 to 60 carbon atoms) amino group , At least one selected from the group consisting of a di (substituted or unsubstituted aryl having 6 to 60 carbon atoms) amino group, and each of Z ₁ to Z ₂ is the same or different from each other, and may form a condensed ring with a group adjacent to each other. .

In addition, in [Chemical Formula 1],

The X ₁ and X ₂ are each independently a substituted or unsubstituted arylene group having 6 to 30 carbon atoms or a single bond, and X ₁ and X ₂ may be bonded to each other,

The Y ₁ and Y ₂ are each independently a substituted or unsubstituted aryl group having 6 to 24 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 24 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 24 carbon atoms, a substituted Or an unsubstituted C1-C24 heteroalkyl group, a substituted or unsubstituted C3-C24 cycloalkyl group, a substituted or unsubstituted C1-C24 alkoxy group, a cyano group, a halogen group, a substituted or unsubstituted carbon number 1 from the group consisting of 6 to 24 aryloxy groups, substituted or unsubstituted alkylsilyl groups having 1 to 40 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 30 carbon atoms, germanium, phosphorus, boron, deuterium and hydrogen More than one species is selected, and each of Y ₁ to Y ₂ is the same as or different from each other, and may form a condensed ring of an aliphatic, aromatic, aliphatic hetero or aromatic hetero with a group adjacent to each other.

Each of l and m is an integer of 1 to 20, and n is an integer of 1 to 4.

In addition, in [Chemical Formula 2],

C _y is a substituted or unsubstituted cycloalkyl having 3 to 8 carbon atoms, b is an integer of 1 to 4, but when b is 2 or more, each cycloalkane may be in a fused form, and the hydrogen substituted thereto Each may be substituted with deuterium or alkyl, and may be the same as or different from each other.

Also above B Is a single bond or -[C(R ₅ )(R ₆ )] _p -, wherein p is an integer of 1 to 3, but when p is 2 or more, 2 or more R ₅ and R ₆ are the same or different from each other;

The R ₁ , R ₂ , R _3, R ₅ and R ₆ are independently of each other, hydrogen, deuterium, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, a carboxyl group, or A salt thereof, a sulfonic acid group or a salt thereof, phosphoric acid or a salt thereof, a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 60 carbon atoms , A substituted or unsubstituted alkoxy group having 1 to 60 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 60 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms, a substituted or unsubstituted carbon number 6 to 60 aryl group, substituted or unsubstituted aryloxy group having 5 to 60 carbon atoms, substituted or unsubstituted arylthio group having 5 to 60 carbon atoms, substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, substituted Or an unsubstituted C1-C60 (alkyl) amino group, a di(substituted or unsubstituted C1-C60 alkyl) amino group, or a (substituted or unsubstituted C6-C60 aryl) amino group, a di(substituted or Unsubstituted C6-C60 aryl) amino group, a substituted or unsubstituted C1-C40 alkylsilyl group, a substituted or unsubstituted C6-C30 arylsilyl group, germanium, phosphorus, it may be selected from boron, ,

a is an integer of 1 to 4, but when a is 2 or more, 2 or more R ₃ are the same as or different from each other, and when R ₃ is plural, each R ₃ may be a fused form, and n is 1 to 4 It is an integer.

In addition, the amine group bonded to A of [Formula 1] and [Formula 2] may be represented by any one selected from the group represented by the following [Substituent 1] to [Substituent 52], but is not limited thereto.

[Substituent 1] [Substituent 2] [Substituent 3]

[Substituent 4] [Substituent 5] [Substituent 6]

[Substituent 7] [Substituent 8] [Substituent 9]

[Substituent 10] [Substituent 11] [Substituent 12]

[Substituent 13] [Substituent 14] [Substituent 15]

[Substituent 16] [Substituent 17] [Substituent 18]

[Substituent 19] [Substituent 20] [Substituent 21]

[Substituent 22] [Substituent 23] [Substituent 24]

[Substituent 25] [Substituent 26] [Substituent 27]

[Substituent 28] [Substituent 29] [Substituent 30]

[Substituent 31] [Substituent 32] [Substituent 33]

[Substituent 34] [Substituent 35] [Substituent 36]

[Substituent 37] [Substituent 38] [Substituent 39]

[Substituent 40] [Substituent 41] [Substituent 42]

[Substituent 43] [Substituent 44] [Substituent 45]

[Substituent 46] [Substituent 47] [Substituent 48]

[Substituent 49] [Substituent 50] [Substituent 51]

[Substituent 52]

In the above substituents, R is the same as or independently of each other, hydrogen, deuterium, halogen atom, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine, hydrazone, carboxyl group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid Or a salt thereof, a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 60 carbon atoms, a substituted or unsubstituted C 1 to carbon number 60 alkoxy group, substituted or unsubstituted C1-C60 alkylthio group (alkylthio), substituted or unsubstituted C3-C60 cycloalkyl group, substituted or unsubstituted C6-C60 aryl group, substituted or Unsubstituted C 5 to C 60 aryloxy group, substituted or unsubstituted C 5 to C 60 arylthio group, substituted or unsubstituted C 2 to C 60 heteroaryl group, substituted or unsubstituted C 1 to C 60 (Alkyl) amino group, di (substituted or unsubstituted alkyl having 1 to 60 carbon atoms) amino group, or (substituted or unsubstituted aryl having 6 to 60 carbon atoms) amino group, di (substituted or unsubstituted aryl having 6 to 60 carbon atoms ) Can be selected from amino group, substituted or unsubstituted C1-C40 alkylsilyl group, substituted or unsubstituted C6-C30 arylsilyl group, germanium, phosphorus, boron, each 1 to 12 And each substituent may form a condensed ring with a group adjacent to each other.

Hereinafter, the present invention will be described in more detail with reference to preferred embodiments. However, these examples are intended to illustrate the present invention in more detail, and it will be apparent to those of ordinary skill in the art that the scope of the present invention is not limited thereto.

(Example)

Synthesis Example 1: Synthesis of Compound 5

Synthesis Example 1-(1): Synthesis of Intermediate 1-a

Intermediate 1-a was synthesized according to Scheme 1 below:

<Reaction Scheme 1>

<Intermediate 1-a>

In a 500 mL round bottom flask reactor (10-phenyl(d5)-anthracene-9-boronic acid (38.6g, 127mmol), 1-bromo-4-iodobenzene (30.0g, 106 mmol), tetrakis (triphenyl) Phosphine) palladium (3.43 g, 3 mmol) and potassium carbonate (27.35 g, 197.9 mmol) were added, and 150 mL of toluene, 150 mL of tetrahydrofuran, and 60 mL of water were added.The temperature of the reactor was raised to 90 degrees and stirred overnight. When the reaction was completed, the temperature of the reactor was lowered to room temperature, extracted with ethyl acetate, and the organic layer was separated, the organic layer was concentrated under reduced pressure and then separated by column chromatography to obtain <Intermediate 1-a> (35.0g, 79.7%).

Synthesis Example 1-(2): Synthesis of Intermediate 1-b

Intermediate 1-b was synthesized according to Scheme 2 below:

<Reaction Scheme 2>

<Intermediate 1-b>

In a well-dried 2L round bottom flask reactor, 1,3-dimethoxybenzene (100.0g, 0.724mol) and 800ml of tetrahydrofuran were added and dissolved. The reaction solution was cooled to -10 degrees in a nitrogen atmosphere, and then normal butyl lithium (543ml, 0.868mol) was slowly added dropwise. After stirring at the same temperature for 4 hours, it was cooled to -78 degrees. While maintaining the same temperature, trimethyl boride (112.8 g, 1.086 mol) was slowly added dropwise for 30 minutes, followed by stirring at room temperature overnight. After completion of the reaction, 2-normal hydrochloric acid was slowly added dropwise to acidify. After extraction with water and ethyl acetate, the organic layer was separated, and moisture was removed with magnesium sulfate. The material was concentrated under reduced pressure and then crystallized from heptane. The resulting solid is filtered and washed with heptane.

<Intermediate 1-b> was obtained. (92.0g, 69%)

Synthesis Example 1-(3): Synthesis of Intermediate 1-c

Intermediate 1-c was synthesized according to Scheme 3 below:

<Reaction Scheme 3>

<Intermediate 1-b> <Intermediate 1-c>

In a 2L round bottom flask reactor, 1-bromo-2-fluorobenzene (80.0g, 0.457mol), <intermediate 1-b> (91.5g, 0.503mol), tetrakis (triphenylphosphine) palladium (11.6g) , 0.01 mol), potassium carbonate (126.4 g, 0.914 mol) was added, and toluene 400 mL, tetrahydrofuran 400 mL, and water 160 mL were added. The temperature of the reactor was raised to 80 degrees and stirred overnight. When the reaction was completed, the temperature of the reactor was lowered to room temperature, extracted with ethyl acetate, and the organic layer was separated. The organic layer was concentrated under reduced pressure and then separated by column chromatography to obtain <Intermediate 1-c>. (85.0g, 80%)

Synthesis Example 1-(4): Synthesis of Intermediate 1-d

Intermediate 1-d was synthesized according to Scheme 4 below:

<Reaction Scheme 4>

<Intermediate 1-c> <Intermediate 1-d>

<Intermediate 1-c> (85.0g, 0.366mol) was placed in a 2L round bottom flask reactor, 510ml of acetic acid and 340ml of hydrobromic acid were added, followed by reflux stirring overnight. When the reaction was completed, the mixture was cooled to room temperature and added dropwise to 1000 ml of cold water. The solution was extracted with water and ethyl acetate to separate the organic layer. The organic layer was washed with 400 ml of aqueous sodium hydrogen carbonate solution and then concentrated under reduced pressure. The material was separated and purified by column chromatography to obtain <Intermediate 1-d>. (71g, 95%)

Synthesis Example 1-(5): Synthesis of Intermediate 1-e

Intermediate 1-e was synthesized according to Scheme 5 below:

<Reaction Scheme 5>

<Intermediate 1-d> <Intermediate 1-e>

In a 2L round bottom flask reactor, <intermediate 1-d> (71.0, 39mmol), potassium carbonate (96.1g, 0.695mol), and 1060ml of 1-methyl-2-pyrrolidinone were added and stirred at 120°C overnight. Upon completion of the reaction, it was added dropwise to 1000 ml of cold water after cooling to room temperature. After extraction with water and ethyl acetate, the organic layer was separated and concentrated under reduced pressure. The material was separated and purified by column chromatography to obtain <Intermediate 1-e>. (60.0g, 93.7%)

Synthesis Example 1- (6): Synthesis of Intermediate 1-f

Intermediate 1-f was synthesized according to Scheme 6:

<Reaction Scheme 6>

<Intermediate 1-e> <Intermediate 1-f>

After dissolving <Intermediate 1-e> (60.0g, 0.326mol) and 600ml of methylene chloride in a 2L round bottom flask reactor, pyridine (38.7g, 0.489mol) was slowly added and stirred at room temperature for 30 minutes. After cooling the reaction solution to 0 degrees, trifluoromethanesulfonyl anhydride (137.8 g, 0.489 mol) was added dropwise while maintaining the same temperature. After stirring at room temperature for 5 hours, 100 ml of water was slowly added to the reaction solution and stirred for 10 minutes. After extraction with water and ethyl acetate, the organic layer was separated and concentrated under reduced pressure. The material was separated and purified by column chromatography to obtain <Intermediate 1-f>. (87g, 84.5%)

Synthesis Example 1- (7): Synthesis of Intermediate 1-g

Intermediate 1-g was synthesized according to Scheme 7 below:

<Reaction Scheme 7>

<Intermediate 1-f> <Intermediate 1-g>

In a 2L round bottom flask reactor <Intermediate 1-f> (87.0g, 0.275mol), bis(pinacolato)diboron (83.8g, 0.330mol), 1,1'-bis(diphenylphosphino)ferrocene- Palladium (II) dichloride (4.5 g, 0.006 mol), potassium acetate (54.0 g, 0.550 mol), and 870 ml of 1,4-dioxane were added and stirred under reflux overnight. After completion of the reaction, the filtrate was concentrated under reduced pressure by passing through a pad of Celite. The material was separated and purified by column chromatography to obtain <Intermediate 1-g>. (65.3g, 80.7%)

Synthesis Example 1- (8): Synthesis of Compound 1

Compound 1 was synthesized according to Scheme 8 below:

<Reaction Scheme 8>

<Intermediate 1-a> <Intermediate 1-g> <Compound 1>

In a 250mL round bottom flask reactor <Intermediate 1-a> (5.5g, 13mmol), <Intermediate 1-g> (4.7g, 16 mmol), tetrakis (triphenylphosphine) palladium (0.46g, 3mmol), potassium Carbonate (3.67 g, 26.5 mmol) was added, and 30 mL of toluene, 30 mL of 1,4-dioxane, and 11 mL of water were added. The temperature of the reactor was raised to 90 degrees and stirred overnight. When the reaction was completed, the temperature of the reactor was lowered to room temperature, extracted with ethyl acetate, and the organic layer was separated. The organic layer was concentrated under reduced pressure and then separated by column chromatography. Recrystallized from toluene and acetone to obtain <Compound 1> (3.2g, 48%).

MS: m/z 502.2 [M ⁺ ]

Synthesis Example 2: Synthesis of Compound 13

Synthesis Example 2-(1): Synthesis of <Intermediate 2-a>

Intermediate 2-a was synthesized according to Scheme 9 below:

<Reaction Scheme 9>

<Intermediate 2-a>

In a 2L round bottom flask reactor, 2-bromodibenzofuran (70.0g, 0.283mol), bis(pinacolato)diboron (86.3g, 0.340mol), 1,1'-bis(diphenylphosphino)ferrocene- Palladium (II) dichloride (4.6 g, 0.006 mol), potassium acetate (56.6 g, 0.567 mol), and 700 ml of 1,4-dioxane were added and stirred under reflux overnight. After completion of the reaction, the filtrate was concentrated under reduced pressure by passing through a pad of Celite. The material was separated and purified by column chromatography to obtain <Intermediate 2-a>. (66.4g, 79%)

Synthesis Example 2- (2): Synthesis of Compound 13

Compound 13 was synthesized according to Scheme 10 below:

<Reaction Scheme 10>

<Intermediate 1-a> <Intermediate 2-a> <Compound 13>

<Compound 13> (3.0 g, 66.1%) was obtained using the same method except that <Intermediate 2-a> was used instead of <Intermediate 1-g> in Synthesis Example 1-(8).

MS: m/z 502.2 [M ⁺ ]

Synthesis Example 3: Synthesis of Compound 22

Synthesis Example 3-(1): Synthesis of Intermediate 3-a

Intermediate 3-a was synthesized according to Scheme 11 below:

<Reaction Scheme 11>

<Intermediate 3-a>

Using the same method except that 1-bromo-3-iodobenzene was used instead of 1-bromo-4-iodobenzene in Synthesis Example 1-(1) <Intermediate 3-a> (32 g, 72.8%) was obtained.

Synthesis Example 3- (2): Synthesis of Compound 22

Compound 22 was synthesized according to Scheme 12 below:

<Reaction Scheme 12>

<Intermediate 3-a> <Intermediate 1-g> <Compound 22>

<Compound 22> (3.5 g, 57.8%) was obtained using the same method except that <Intermediate 3-a> was used instead of <Intermediate 1-a> in Synthesis Example 1-(8).

MS: m/z 502.2 [M ⁺ ]

Synthesis Example 4: Synthesis of Compound 31

Synthesis Example 4- (1): Synthesis of Compound 31

Compound 31 was synthesized according to Scheme 13 below:

<Reaction Scheme 13>

<Intermediate 3-a> <Intermediate 2-a> <Compound 31>

<Compound 31> (2.7 g, 44.6%) was obtained using the same method except that <Intermediate 3-a> was used instead of <Intermediate 1-a> in Synthesis Example 2-(2).

MS: m/z 502.2 [M ⁺ ]

Synthesis Example 5: Synthesis of Compound 43

Synthesis Example 5-(1): Synthesis of Intermediate 5-a

Intermediate 5-a was synthesized according to Scheme 14 below:

<Reaction Scheme 14>

<Intermediate 5-a>

<Intermediate 5-a> (29 g, 59.5%) using the same method except that 1,4-dibromonaphthalene was used instead of 1-bromo-4-iodobenzene in Synthesis Example 1-(1). ).

Synthesis Example 5- (2): Synthesis of Compound 43

Compound 43 was synthesized according to Scheme 15 below:

<Reaction Scheme 15>

<Intermediate 5-a> <Intermediate 1-g> <Compound 43>

<Compound 43> (4.2 g, 69.4%) was obtained using the same method except that <Intermediate 5-a> was used instead of <Intermediate 1-a> in Synthesis Example 1-(8).

MS: m/z 552.2 [M ⁺ ]

Synthesis Example 6: Synthesis of Compound 52

Synthesis Example 6-(1): Synthesis of Compound 52

Compound 52 was synthesized according to Scheme 16 below:

<Reaction Scheme 16>

<Intermediate 5-a> <Intermediate 2-a> <Compound 52>

<Compound 52> (4.0 g, 67.4%) was obtained using the same method except that <Intermediate 5-a> was used instead of <Intermediate 1-a> in Synthesis Example 2-(2).

MS: m/z 552.2 [M ⁺ ]

Synthesis Example 7: Synthesis of Compound 61

Synthesis Example 7-(1): Synthesis of Intermediate 7-a

Intermediate 7-a was synthesized according to Scheme 17 below:

<Scheme 17>

<Intermediate 7-a>

<Intermediate 7-a> (244 g, 95%) was obtained using the same method except that 1,4-dihydroxynaphthalene was used instead of <Intermediate 1-e> in Synthesis Example 1-(6). .

Synthesis Example 7-(2): Synthesis of Intermediate 7-b

Intermediate 7-b was synthesized according to Scheme 18 below:

<Reaction Scheme 18>

<Intermediate 7-a> <Intermediate 7-b>

In a 2L round bottom flask reactor <Intermediate 7-a> (110.0g, 0.259mol), 10-phenyl (d5)-anthracene-9-boronic acid (78.6g, 0.259mol), tetrakis (triphenylphosphine) palladium (6.0g, 5 mmol) and potassium carbonate (71.7 g, 0.519 mol) were added, and toluene 770 mL, ethanol 330 mL, and water 220 mL were added. The temperature of the reactor was raised to 60 degrees and stirred for 1 hour. When the reaction was completed, the temperature of the reactor was lowered to room temperature and the produced solid was filtered. The filtrate was extracted with water and ethyl acetate, and the organic layer was separated and concentrated under reduced pressure. The material was dissolved in toluene and recrystallized with methanol to obtain <Intermediate 7-b>. (100.0g, 72.3%)

Synthesis Example 7-(3): Synthesis of Compound 61

Compound 61 was synthesized according to Scheme 19 below:

<Reaction Scheme 19>

<Intermediate 7-b> <Intermediate 1-g> <Compound 61>

<Compound 61> (2.8g, 54%) was obtained using the same method except that <Intermediate 7-b> was used instead of <Intermediate 1-a> in Synthesis Example 1-(8).

MS: m/z 552.2 [M ⁺ ]

Synthesis Example 8: Synthesis of Compound 70

Synthesis Example 8-(1): Synthesis of Compound 70

Compound 70 was synthesized according to Scheme 20 below.

<Reaction Scheme 20>

<Intermediate 7-b> <Intermediate 2-a> <Compound 70>

<Compound 70> (2.4 g, 46%) was obtained using the same method, except that <Intermediate 7-b> was used instead of <Intermediate 1-a> in Synthesis Example 2-(2).

MS: m/z 552.2 [M ⁺ ]

Synthesis Example 9: Synthesis of Compound 118

Synthesis Example 9-(1): Synthesis of Compound 118

Compound 118 was synthesized according to Scheme 21 below.

<Reaction Scheme 21>

<Intermediate 9-a> <Compound 118>

In Synthesis Examples 7-(2) and 7-(3), 10-phenyl (d5)-anthracene-9-boronic acid, respectively, instead of <Intermediate 7-b>, 10-phenyl (H5)-anthracene-9-boronic acid , <Compound 118> (3.5g, 58%) was obtained using the same method, except that <Intermediate 9-a> was used.

MS: m/z 547.2 [M ⁺ ]

Examples 1 to 7: Preparation of organic light emitting device

The ITO glass was patterned so that the light emitting area was 2mm*mm and washed. After mounting the ITO glass in the vacuum chamber base pressure of 1 - 10 ^- After allowing the ⁷ torr was deposited over the ITO by HAT-CN (50 Å), α-NPD (600 Å) in order. The light emitting layer is formed by mixing the host and BD1 (5 wt%) shown in Table 1 below (200Å), and then, as an electron transport layer, [Chemical Formula E-1] and [Chemical Formula E-2] in a ratio of 1:1 are 300 Å, [Chemical Formula E-1] was formed as an electron injection layer in the order of 10 Å and Al (1000 Å) to manufacture an organic light-emitting device. The emission characteristics of the organic light emitting device were measured at 0.4 mA.

[HAT-CN] [α-NPD]

[Formula E-1] [Formula E-2] [BD1]

Comparative Examples 1 to 7

An organic light-emitting device was manufactured in the same manner except for using [BH1] to [BH7] instead of the compounds used in Examples 1 to 7, and the structures of [BH1] to [BH7] are as follows.

[BH1] [BH2] [BH3]

[BH4] [BH5] [BH6] [BH7]

For the organic light emitting devices manufactured according to Examples 1 to 7 and Comparative Examples 1 to 7, the driving voltage was measured and the results are shown in Table 1 below. The voltage was measured at a current density of 10 mA/cm ² .

Host Driving voltage (V) Host Driving voltage (V) Example 1 Compound 1 3.57 Comparative Example 1 BH1 3.97 Example 2 Compound 13 3.54 Comparative Example 2 BH2 3.85 Example 3 Compound 22 3.74 Comparative Example 3 BH3 3.9 Example 4 Compound 31 3.73 Comparative Example 4 BH4 3.78 Example 5 Compound 84 3.64 Comparative Example 5 BH5 3.8 Example 6 Compound 52 3.53 Comparative Example 6 BH6 3.98 Example 7 Compound 70 3.51 Comparative Example 7 BH7 3.9

As shown in the evaluation results of [Table 1], it can be seen that the organic light-emitting device using the compound of the structure according to the embodiment of the present invention has a lower driving voltage of the organic light-emitting device compared to the organic light-emitting device according to the comparative example.

Claims (10)

An organic light emitting compound represented by the following [Chemical Formula A].
[Formula A]

In the above [Formula A],
R ₂ to R ₅ are each the same or different, and independently of each other, hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted carbon number 2 to 30 alkynyl group, substituted or unsubstituted C 3 to C 30 cycloalkyl group, substituted or unsubstituted C 5 to C 30 cycloalkenyl group, substituted or unsubstituted C 1 to C 30 alkoxy group, substituted or unsubstituted A substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkyl thioxy group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthioxy group having 5 to 30 carbon atoms, a substituted or unsubstituted alkyl having 1 to 30 carbon atoms An amine group, a substituted or unsubstituted arylamine group having 5 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted hetero atom having O, N or S as a hetero atom and having 2 to 50 carbon atoms Aryl group, cyano group, nitro group, halogen group, substituted or unsubstituted silyl group having 1 to 30 carbon atoms, substituted or unsubstituted germanium group having 1 to 30 carbon atoms, substituted or unsubstituted boron group having 1 to 30 carbon atoms , Substituted or unsubstituted aluminum group having 1 to 30 carbon atoms, carbonyl group, phosphoryl group, amino group, thiol group, hydroxy group, selenium group, tellurium group, amide group, ether group and ester group,
Hydrogen is bonded to the carbon of the aromatic ring to which the substituents of R ₂ to R ₅ are not bonded,
The linking group L is a single bond, a substituted or unsubstituted arylene group having 6 to 60 carbon atoms;
l to n are each the same or different from each other, and are independently an integer of 1 to 4,
o is an integer from 1 to 3,
When the l to o are each 2 or more, each of R ₂ to R ₅ is the same as or different from each other,
R ₁ is deuterium, k is 5,
'***' of X is a binding site that binds to the connector L,
'Substituted'in'substituted or unsubstituted' in the [Chemical Formula A] is deuterium, cyano group, halogen group, hydroxy group, nitro group, alkyl group having 1 to 24 carbon atoms, halogenated alkyl group having 1 to 24 carbon atoms, carbon number 1 to 24 alkenyl group, C 1 to C 24 alkynyl group, C 1 to C 24 heteroalkyl group, C 6 to 24 aryl group, C 6 to C 24 arylalkyl group, C 2 to C 24 heteroaryl group or C 2 To 24 heteroarylalkyl group, C 1 to C 24 alkoxy group, C 1 to C 24 alkylamino group, C 1 to C 24 arylamino group, C 1 to C 24 hetero arylamino group, C 1 to C 24 alkylsilyl group, C carbon number It means substituted with one or more substituents selected from the group consisting of an arylsilyl group of 1 to 24 and an aryloxy group of 1 to 24 carbon atoms. The method of claim 1,
The linking group L is a single bond, or an organic light emitting compound, characterized in that any one selected from the following [Structural Formula 1] or [Structural Formula 2].
[Structural Formula 1] [Structural Formula 2]

In the linking group L, hydrogen or deuterium may be bonded to the carbon site of the aromatic ring. The method of claim 1,
The organic light-emitting compound, characterized in that R ₂ and/or R ₃ is deuterium, and l is 2 or more or m is 2 or more. The method of claim 1,
The R ₄ and/or R ₅ is deuterium, and n is 2 or more or o is 2 or more. The method of claim 1,
The organic light-emitting compound is any one selected from the group represented by the following [Chemical Formula 1] to [Compound 99], [Compound 130], [Compound 131], [Compound 134], and [Compound 138] compound.

<Compound 1><Compound2><Compound3>

<Compound 4><Compound5><Compound6>

<Compound 7><Compound8><Compound9>

<Compound 10><Compound11><Compound12>

<Compound 13><Compound14><Compound15>

<Compound 16><Compound17><Compound18>

<Compound 19><Compound20><Compound21>

<Compound 22><Compound23><Compound24>

<Compound 25><Compound26><Compound27>

<Compound 28><Compound29><Compound30>

<Compound 31><Compound32><Compound33>

<Compound 34><Compound35><Compound36>

<Compound 37><Compound38><Compound39>

<Compound 40><Compound41><Compound42>

<Compound 43><Compound44><Compound45>

<Compound 46><Compound47><Compound48>

<Compound 49><Compound50><Compound51>

<Compound 52><Compound53><Compound54>

<Compound 55><Compound56><Compound57>

<Compound 58><Compound59><Compound60>

<Compound 61><Compound62><Compound63>

<Compound 64><Compound65><Compound66>

<Compound 67><Compound68><Compound69>

<Compound 70><Compound71><Compound72>

<Compound 73><Compound74><Compound75>

<Compound 76><Compound77><Compound78>

<Compound 79><Compound80><Compound81>

<Compound 82><Compound83><Compound84>

<Compound 85><Compound86><Compound87>

<Compound 88><Compound89><Compound90>

<Compound 91><Compound92><Compound93>

<Compound 94><Compound95><Compound96>

<Compound 97><Compound98><Compound99>

<Compound 130><Compound131>

<Compound 134><Compound138> A first electrode;
A second electrode facing the first electrode; And
An organic light-emitting device comprising: an organic layer interposed between the first electrode and the second electrode, wherein the organic layer includes at least one compound of any one selected from claims 1 to 5. The method of claim 6,
The organic layer is an organic light emitting device comprising at least one of a hole injection layer, a hole transport layer, a functional layer having a hole injection function and a hole transport function at the same time, a light emitting layer, an electron transport layer, and an electron injection layer. The method of claim 7,
An organic light-emitting device, wherein the organic layer interposed between the first electrode and the second electrode is an emission layer, the emission layer is formed of a host and a dopant, and the organic emission compound is used as a host. The method of claim 7,
One or more layers selected from each of the layers are formed by a deposition process or a solution process. The method of claim 8,
The organic light emitting device may include a flat panel display device; Flexible display device; Monochrome or white flat lighting devices; And, a single color or white flexible lighting device; Organic light emitting device, characterized in that used in any one device selected from.

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