KR102309065B1 - 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 [Formula A] and an organic light emitting device comprising 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

The present invention relates to a compound for an organic light emitting device capable of realizing an organic light emitting device with a low driving voltage, and an organic light emitting device comprising the same, and more particularly, when used as a fluorescent host, excellent device characteristics 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-luminescence phenomenon, has a large viewing angle, can be lightweight and compact compared to a liquid crystal display, and has advantages such as a fast response speed. ) is expected to be applied to displays or lighting.

In general, the organic light emitting phenomenon refers to a phenomenon in which electric energy is converted into light energy using an organic material. An organic light emitting device using an organic light emitting phenomenon generally has a structure including an anode and a cathode and an organic material layer therebetween. Here, the organic layer is often formed 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, 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 the organic light emitting device, when a voltage is applied between the two electrodes, holes are injected into the organic material layer from the anode and electrons from the cathode are injected into the organic material layer. When the injected holes and electrons meet, excitons are formed, and the excitons When it falls back to the ground state, it lights up. Such an organic light emitting device is known to have characteristics such as self-luminescence, high luminance, high efficiency, low driving voltage, wide viewing angle, high contrast, and high-speed response.

A material used as an organic layer in an organic light emitting device may be classified into a light emitting material and a charge transport material, for example, a hole injection material, a hole transport material, an electron transport material, an electron injection material, and the like, according to functions. The light emitting material can be classified into a high molecular type and a low molecular type according to molecular weight, and can be classified into a fluorescent material derived from a singlet excited state of an electron and a phosphorescent material derived from a triplet excited state of an electron according to a light emitting mechanism. . In addition, the light emitting material may be divided 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 emission color.

On the other hand, when only one material is used as a light emitting material, the maximum emission wavelength is shifted to a longer wavelength due to intermolecular interaction, and there is a problem in that the color purity is lowered or the efficiency of the device is decreased due to the emission attenuation effect. Therefore, increase in color purity and energy A host-dopant system can be used as a luminescent material to increase the luminous efficiency through transition.

The principle is that when a small amount of a dopant having a smaller energy band gap than that of a host forming the emission layer is mixed in the emission layer, excitons generated in the emission 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 band of the dopant, light having a desired wavelength may be obtained according to the type of the dopant used.

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

However, despite the preparation of various types of compounds for use in the light emitting medium layer including the prior art, the need for the development of an organic material layer material for an organic light emitting device capable of driving the organic light emitting device at a lower voltage is still ongoing. is being demanded.

Registered Patent Publication No. 10-0910150 (2009.08.03)

Japanese 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 [Formula A] in order to achieve the first technical problem.

[Formula A]

In the [Formula A],

R ₁ to R ₅ are the same or different, and each independently represents hydrogen, deuterium, a substituted or unsubstituted C 1 to C 30 alkyl group, a substituted or unsubstituted C 2 to C 30 alkenyl group, a substituted or unsubstituted C number 2 to 30 alkynyl group, substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, substituted or unsubstituted cycloalkenyl group having 5 to 30 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, substituted or unsubstituted A substituted or unsubstituted C6-C30 aryloxy group, a substituted or unsubstituted C1-C30 alkylthioxy group, a substituted or unsubstituted C5-C30 arylthioxy group, a substituted or unsubstituted C1-C30 alkyl An amine group, a substituted or unsubstituted C 5 to C 30 arylamine group, a substituted or unsubstituted C 6 to C 50 aryl group, a substituted or unsubstituted C 2 to C 50 hetero atom having O, N or S as a hetero atom Aryl group, cyano group, nitro group, halogen group, substituted or unsubstituted C1-C30 silyl group, substituted or unsubstituted C1-C30 germanium group, substituted or unsubstituted C1-C30 boron group , a substituted or unsubstituted aluminum group having 1 to 30 carbon atoms, 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 the 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 as or different from each other, and each independently an integer of 1 to 4,

o is an integer from 1 to 3,

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

'***' of X may be a binding site binding to the linking group L.

In addition, the present invention in order to achieve the second object, a first electrode; a second electrode opposite 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 [Formula A] has excellent characteristics, enabling 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 [Formula A] as a novel aromatic organic light emitting compound.

[Formula A]

R ₁ to R ₅ are the same or different, and each independently represents hydrogen, deuterium, a substituted or unsubstituted C 1 to C 30 alkyl group, a substituted or unsubstituted C 2 to C 30 alkenyl group, a substituted or unsubstituted C number 2 to 30 alkynyl group, substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, substituted or unsubstituted cycloalkenyl group having 5 to 30 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, substituted or unsubstituted A substituted or unsubstituted C6-C30 aryloxy group, a substituted or unsubstituted C1-C30 alkylthioxy group, a substituted or unsubstituted C5-C30 arylthioxy group, a substituted or unsubstituted C1-C30 alkyl An amine group, a substituted or unsubstituted C 5 to C 30 arylamine group, a substituted or unsubstituted C 6 to C 50 aryl group, a substituted or unsubstituted C 2 to C 50 hetero atom having O, N or S as a hetero atom Aryl group, cyano group, nitro group, halogen group, substituted or unsubstituted C1-C30 silyl group, substituted or unsubstituted C1-C30 germanium group, substituted or unsubstituted C1-C30 boron group , a substituted or unsubstituted aluminum group having 1 to 30 carbon atoms, 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 the 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 as or different from each other, and each independently an integer of 1 to 4,

o is an integer from 1 to 3,

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

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

'Substitution' in 'substituted or unsubstituted' in [Formula A] is deuterium, a cyano group, a halogen group, a hydroxyl group, a nitro group, an alkyl group having 1 to 24 carbon atoms, a halogenated alkyl group having 1 to 24 carbon atoms, a carbon number A 1 to 24 alkenyl group, an alkynyl group having 1 to 24 carbon atoms, a heteroalkyl group having 1 to 24 carbon atoms, an aryl group having 6 to 24 carbon atoms, an arylalkyl group having 6 to 24 carbon atoms, a heteroaryl group having 2 to 24 carbon atoms, or 2 carbon atoms to 24 heteroarylalkyl group, C1-C24 alkoxy group, C1-C24 alkylamino group, C1-C24 arylamino group, C1-C24 heteroarylamino group, C1-C24 alkylsilyl group, carbon number It means to be substituted with one or more substituents selected from the group consisting of an arylsilyl group having 1 to 24 and an aryloxy group having 1 to 24 carbon atoms.

In addition, considering the range of the alkyl group or aryl group in the "substituted or unsubstituted C1-C24 alkyl group", "substituted or unsubstituted C6-C24 aryl group", etc., the C1-C24 The range of carbon number of the alkyl group and the aryl group having 6 to 24 carbon atoms means the total number of carbon atoms constituting the alkyl portion or the aryl portion when viewed as unsubstituted without considering the portion in which the substituent is substituted. 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 including one or more rings, and when the aryl group has a substituent, it is fused with neighboring substituents to form an additional ring. 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, and aromatic groups such as pyrenyl, indenyl, fluorenyl, tetrahydronaphthyl, peryleneyl, chrysenyl, naphthacenyl, fluoranthenyl, and the like, wherein at least one hydrogen atom of the aryl group is a deuterium atom, a halogen atom , a hydroxyl group, a nitro group, a cyano group, a silyl group, an amino group (-NH ₂ , -NH(R), -N(R')(R''), R' and R" are each independently of each other having 1 to 10 carbon atoms an 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, halogenated alkyl group having 1 to 24 carbon atoms. of an alkenyl group, an alkynyl group having 1 to 24 carbon atoms, a heteroalkyl group having 1 to 24 carbon atoms, an aryl group having 6 to 24 carbon atoms, an arylalkyl group having 6 to 24 carbon atoms, a heteroaryl group having 2 to 24 carbon atoms, or a heteroaryl group having 2 to 24 carbon atoms. It may be substituted with a heteroarylalkyl group.

The heteroaryl group, which is a substituent used in the compound of the present invention, includes 1, 2 or 3 heteroatoms selected from N, O, P or S, and the remaining ring atoms are carbon atoms It means a ring aromatic system having 2 to 24 carbon atoms, The rings may be fused to form a ring. And one or more hydrogen atoms in the heteroaryl group may be substituted with the same substituents 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 of the alkyl group is Atoms can be substituted with the same substituents as in the case of the above aryl group.

Specific examples of the alkoxy group as a substituent used in the compound of the present invention include methoxy, ethoxy, propoxy, isobutyloxy, sec-butyloxy, pentyloxy, iso-amyloxy, hexyloxy and the like, One or more hydrogen atoms in the alkoxy group may be substituted with the same substituents 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, and 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 compound represented by Formula A in the present invention, the linking group L bonded to the 9th position of the anthracene ring is 1 or 2 of either phenyl ring of a substituted or unsubstituted dibenzofuran, as shown in Figure 1 below. It is technically characterized by bonding with the carbon atom at the burn position.

[그림 1]

[Figure 1]

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

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

[Structural Formula 1] [Structural Formula 2]

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

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

L1 L2 L3 L4 L5 L6

Here, '-*' is a binding site bonded to anthracene, and '-**' is a binding site bonded 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.

In an embodiment, the substituent R ₁ may be deuterium, and k may be 5.

In one embodiment, R ₂ and/or R ₃ may be deuterium, and l may be 2 or more, or m may be 2 or more.

In one embodiment, as R ₂ and R ₃ are deuterium at the same time, l and m may be 2 or more, respectively.

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 may be deuterium at the same time, and n and o may be 2 or more, respectively.

Hereinafter, any one compound selected from the group represented by the following [Formula 1] to [Formula 138] is shown as a representative structural formula of the organic light emitting compound of the present invention, 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 opposite 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 in the present invention.

In the present invention, "(organic layer) includes one or more compounds" means "(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. can be interpreted as "there is

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 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.

In addition, in 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 consists 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 compound, hydrazone compound, deuterium substituted hydrazone compound, carbazole compound, deuterium substituted carbazole compound, stilbene compound, deuterium substituted stilbene compound, starburst compound, deuterium substituted starburst compounds, oxadiazole compounds, deuterium substituted oxadiazole compounds, coumarin, deuterium substituted coumarin, and the like may be mentioned, but the present invention is not limited thereto.

When the light emitting layer includes a host and a dopant, the content of the dopant may be generally selected from 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, the 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, and the solution process is to form each layer It refers to a method of mixing a material used as a material for a solvent with a solvent and forming a thin film through methods such as inkjet printing, roll-to-roll coating, screen printing, spray coating, dip coating, spin coating, and the like.

In addition, the organic light emitting device in the present invention is a flat panel display device; flexible display devices; devices for flat-panel lighting, either monochromatic or white; And monochromatic 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, Hole Transport Layer) is additionally stacked between the anode and the organic light emitting layer, and an electron transport layer (ETL, Electron Transport Layer) is added between the cathode and the organic light emitting layer. can be stacked with

As a material of the hole transport layer, electron-donating molecules having a small ionization potential are used, and diamine, triamine or tetraamine derivatives having triphenylamine as a basic skeleton are often 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) or the like can be used.

A hole injection layer (HIL, Hole Injecting Layer) may be further laminated on the lower portion of 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) and the like can be used.

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

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

Hereinafter, an 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 electrons. The injection layer 70 may be further included, and in addition to that, it is also possible to further form an intermediate layer of one or two layers.

Referring to FIG. 1, an organic light emitting diode and a manufacturing method thereof of the present invention will be described as follows. First, the anode 20 is formed by coating an anode electrode material 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, handling and waterproofing properties 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.

A hole injection layer 30 is formed by vacuum thermal evaporation or spin coating of a hole injection layer material on the anode 20 electrode. Next, the hole transport layer 40 is formed by vacuum thermal evaporation or spin coating of the hole transport layer material on the hole injection layer 30 .

Subsequently, an organic light emitting layer 50 is laminated on the hole transport layer 40 and a hole blocking layer (not shown) is selectively deposited on the organic light emitting layer 50 by a vacuum deposition method or a spin coating method to form a thin film. can do. The hole blocking layer serves to prevent this problem by using a material having a very low HOMO (Highest Occupied Molecular Orbital) level because the lifetime and efficiency of the device are reduced when holes are introduced into the cathode through the organic light emitting layer. . In this case, the hole blocking material used is not particularly limited, but has an electron transport ability and has an ionization potential higher than that of a light emitting compound, and typically BAlq, BCP, TPBI, etc. 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 metal for forming a cathode is vacuum heated on the electron injection layer 70 . By vapor deposition to form the cathode 80 electrode, the organic EL device is completed. Here, as the metal for forming the cathode, lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver ( Mg-Ag) may be used, and in order to obtain a top light emitting device, a transmissive cathode using ITO or IZO may be used.

In addition, according to a specific example of the present invention, it is preferable that the thickness of the light emitting layer is 50 to 2,000 Å, and the light emitting layer may be composed 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 [Formula 1] or [Formula 2]. In this case, the light emitting layer may further include various dopant materials.

[Formula 1] [Formula 2]

Among the [Formula 1] and [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 and 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 C3 to C50 heteroarylene group, which is substituted or unsubstituted and has 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 Chemical Formulas A1 to A10 below.

[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 of [Formula A3] are hydrogen, a deuterium atom, a substituted or unsubstituted C 1 to C 60 alkyl group, a substituted or unsubstituted C 2 to C 60 alkenyl group, a substituted or unsubstituted C 2 to 60 alkynyl group, substituted or unsubstituted C 1 to C 60 alkoxy group, substituted or unsubstituted C 1 to C 60 alkylthio group, substituted or unsubstituted C 3 to C 60 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 A heteroaryl group, a substituted or unsubstituted (alkyl)amino group having 1 to 60 carbon atoms, a di(substituted or unsubstituted alkyl having 1 to 60 carbon atoms) amino group, or a (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)amino group having 6 to 60 carbon atoms, Z ₁ to Z ₂ are the same or different from each other, and may form a condensed ring with a group adjacent to each other .

In addition, in [Formula 1],

Wherein 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,

wherein Y ₁ and Y ₂ are each independently a substituted or unsubstituted C6-C24 aryl group, a substituted or unsubstituted C2-C24 heteroaryl group, a substituted or unsubstituted C1-C24 alkyl group, 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 a 6 to 24 aryloxy group, a substituted or unsubstituted C 1 to C 40 alkylsilyl group, a substituted or unsubstituted C 6 to C 30 arylsilyl group, 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 aliphatic, aromatic, aliphatic hetero or aromatic hetero with groups 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 [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 substituted hydrogen is 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 from 1 to 3, but when p is 2 or more, 2 or more R ₅ and R ₆ are the same as or different from each other;

Wherein R ₁ , R ₂ , R _{3 ,} R ₅ and R ₆ are each independently hydrogen, deuterium, halogen atom, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine, hydrazone, carboxyl group or A salt thereof, a sulfonic acid group or a salt thereof, phosphoric acid or a salt thereof, a substituted or unsubstituted C 1 to C 60 alkyl group, a substituted or unsubstituted C 2 to C 60 alkenyl group, a substituted or unsubstituted C 2 to C 60 alkynyl group , a substituted or unsubstituted C 1 to C 60 alkoxy group, a substituted or unsubstituted C 1 to C 60 alkylthio group, a substituted or unsubstituted C 3 to C 60 cycloalkyl group, a substituted or unsubstituted C 6 to 60 aryl group, substituted or unsubstituted C5 to C60 aryloxy group, substituted or unsubstituted C5 to C60 arylthio group, substituted or unsubstituted C2 to C60 heteroaryl group, substituted Or an unsubstituted (alkyl)amino group having 1 to 60 carbon atoms, di(substituted or unsubstituted alkyl)amino group having 1 to 60 carbon atoms, or (substituted or unsubstituted aryl)amino group having 6 to 60 carbon atoms, di(substituted or It may be selected from an unsubstituted C 6 to C 60 aryl) amino group, a substituted or unsubstituted C 1 to C 40 alkylsilyl group, a substituted or unsubstituted C 6 to C 30 arylsilyl group, germanium, phosphorus, and boron, ,

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

In addition, the amine group bonded to A of the [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.

[Substitute 1] [Substitute 2] [Substitute 3]

[Substitute 4] [Substitute 5] [Substitute 6]

[Substitute 7] [Substitute 8] [Substitute 9]

[substituent 10] [substituent 11] [substituent 12]

[Substitute 13] [Substitute 14] [Substitute 15]

[Substitute 16] [Substitute 17] [Substitute 18]

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

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

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

[Substitute 28] [Substitute 29] [Substitute 30]

[substituent 31] [substituent 32] [substituent 33]

[Substitute 34] [Substitute 35] [Substitute 36]

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

[Substitute 40] [Substitute 41] [Substitute 42]

[substituent 43] [substituent 44] [substituent 45]

[Substitute 46] [Substitute 47] [Substitute 48]

[Substitute 49] [Substitute 50] [Substitute 51]

[Substitute 52]

In the above substituents, R is the same or independently of each other, hydrogen, deuterium, halogen atom, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine, hydrazone, carboxyl group or a salt thereof, sulfonic acid group or a salt thereof, phosphoric acid or a salt thereof, a substituted or unsubstituted C 1 to C 60 alkyl group, a substituted or unsubstituted C 2 to C 60 alkenyl group, a substituted or unsubstituted C 2 to C 60 alkynyl group, a substituted or unsubstituted C 1 to C 1 A 60 alkoxy group, a substituted or unsubstituted C 1 to C 60 alkylthio group, a substituted or unsubstituted C 3 to C 60 cycloalkyl group, a substituted or unsubstituted C 6 to C 60 aryl group, a substituted or An unsubstituted C5 to C60 aryloxy group, a substituted or unsubstituted C5 to C60 arylthio group, a substituted or unsubstituted C2 to C60 heteroaryl group, a substituted or unsubstituted C1 to C60 (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) ) may be selected from an amino group, a substituted or unsubstituted alkylsilyl group having 1 to 40 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, germanium, phosphorus, and boron, each of which may be substituted by 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 skilled in the art that the scope of the present invention is not limited thereby.

(Example)

Synthesis Example 1: Synthesis of compound 5

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

According to Scheme 1 below, Intermediate 1-a was synthesized:

<Scheme 1>

<Intermediate 1-a>

In a 500mL round-bottom flask reactor (10-phenyl (d5)-anthracene-9-boronic acid (38.6 g, 127 mmol), 1-bromo-4-iodobenzene (30.0 g, 106 mmol), tetrakis (triphenyl) Phosphine) palladium (3.43 g, 3 mmol), potassium carbonate (27.35 g, 197.9 mmol) were added, toluene 150 mL, tetrahydrofuran 150 mL, and water 60 mL 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 separated by column chromatography to obtain <Intermediate 1-a> (35.0 g, 79.7%)

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

Intermediate 1-b was synthesized according to Scheme 2:

<Scheme 2>

<Intermediate 1-b>

In a well-dried 2L round-bottom flask reactor, 1,3-dimethoxybenzene (100.0 g, 0.724 mol) and 800 ml of tetrahydrofuran were put and dissolved. The reaction solution was cooled to -10 degrees in a nitrogen atmosphere, and then n-butyl lithium (543ml, 0.868mol) was slowly added dropwise. After stirring at the same temperature for 4 hours, it was cooled to -78°C. While maintaining the same temperature, trimethylboride (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, 2N 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 was filtered and washed with heptane.

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

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

Intermediate 1-c was synthesized according to Scheme 3:

<Scheme 3>

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

In a 2L round-bottom flask reactor, 1-bromo-2-fluorobenzene (80.0 g, 0.457 mol), <Intermediate 1-b> (91.5 g, 0.503 mol), tetrakis (triphenylphosphine) palladium (11.6 g) , 0.01 mol), potassium carbonate (126.4 g, 0.914 mol) were 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, extraction was performed with ethyl acetate, and the organic layer was separated. The organic layer was concentrated under reduced pressure and separated by column chromatography to obtain <Intermediate 1-c>. (85.0 g, 80%)

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

Intermediate 1-d was synthesized according to Scheme 4:

<Scheme 4>

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

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

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

Intermediate 1-e was synthesized according to Scheme 5:

<Scheme 5>

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

<Intermediate 1-d> (71.0, 39mmol), potassium carbonate (96.1g, 0.695mol), and 1-methyl-2-pyrrolidinone 1060ml were put in a 2L round-bottom flask reactor 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>. (60.0 g, 93.7%)

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

Intermediate 1-f was synthesized according to Scheme 6:

<Scheme 6>

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

In a 2L round-bottom flask reactor, <Intermediate 1-e> (60.0g, 0.326mol) and 600ml of methylene chloride were put and dissolved, and then pyridine (38.7g, 0.489mol) was slowly added and stirred at room temperature for 30 minutes. After the reaction solution was cooled to 0°C, 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. It was extracted with water and ethyl acetate, and 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:

<Scheme 7>

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

In a 2L round-bottom flask reactor, <Intermediate 1-f> (87.0 g, 0.275 mol), bis (pinacolato) diboron (83.8 g, 0.330 mol), 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 it through a celite pad. The material was separated and purified by column chromatography to obtain <Intermediate 1-g>. (65.3 g, 80.7%)

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

Compound 1 was synthesized according to Scheme 8 below:

<Scheme 8>

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

<Intermediate 1-a> (5.5g, 13mmol), <Intermediate 1-g> (4.7g, 16mmol), tetrakis(triphenylphosphine)palladium (0.46g, 3mmol), potassium in a 250mL round-bottom flask reactor Carbonate (3.67 g, 26.5 mmol) was added, and toluene 30 mL, 1,4-dioxane 30 mL, and water 11 mL 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, extraction was performed with ethyl acetate, and the organic layer was separated. The organic layer was concentrated under reduced pressure and then separated by column chromatography. Recrystallization from toluene and acetone gave <Compound 1>. (3.2 g, 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:

<Scheme 9>

<Intermediate 2-a>

2-Bromodibenzofuran (70.0g, 0.283mol), bis(pinacolato)diboron (86.3g, 0.340mol), 1,1'-bis(diphenylphosphino)ferrocene- in a 2L round bottom flask reactor 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 it through a celite pad. The material was separated and purified by column chromatography to obtain <Intermediate 2-a>. (66.4 g, 79%)

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

Compound 13 was synthesized according to Scheme 10:

<Scheme 10>

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

<Compound 13> (3.0 g, 66.1% ) was obtained in the same manner 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:

<Scheme 11>

<Intermediate 3-a>

<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:

<Scheme 12>

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

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

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:

<Scheme 13>

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

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

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:

<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) ) was obtained.

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

Compound 43 was synthesized according to Scheme 15:

<Scheme 15>

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

<Compound 43> (4.2 g, 69.4% ) was obtained in the same manner 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:

<Scheme 16>

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

<Compound 52> (4.0 g, 67.4% ) was obtained in the same manner 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 in the same manner 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:

<Scheme 18>

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

<Intermediate 7-a> (110.0 g, 0.259 mol), 10-phenyl (d5)-anthracene-9-boronic acid (78.6 g, 0.259 mol), tetrakis (triphenylphosphine) palladium in a 2L round-bottom flask reactor (6.0 g, 5 mmol), 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 resulting 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 from methanol to obtain <Intermediate 7-b>. (100.0 g, 72.3%)

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

Compound 61 was synthesized according to Scheme 19:

<Scheme 19>

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

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

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.

<Scheme 20>

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

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

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.

<Scheme 21>

<Intermediate 9-a> <Compound 118>

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

MS: m/z 547.2 [M ⁺ ]

Examples 1 to 7: Preparation of organic light emitting device

After patterning so that the light emitting area of the ITO glass has a size of 2mm x mm, it was washed. After mounting the ITO glass in a vacuum chamber, the base pressure was set to 1 x 10 ^-7 torr, and then HAT-CN (50 Å) and α-NPD (600 Å) were formed on the ITO in this order. The light emitting layer is formed by mixing the host and BD1 (5 wt%) shown in Table 1 below (200 Å), and then [Formula E-1] and [Formula E-2] as an electron transport layer in a 1:1 ratio of 300 Å, [Formula E-1] as an electron injection layer was formed into a film in the order of 10 Å, Al (1000 Å) to prepare an organic light emitting diode. 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 diode was manufactured in the same manner except that [BH1] to [BH7] were used 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 diodes manufactured according to Examples 1 to 7 and Comparative Examples 1 to 7, the results of measuring driving voltages 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 in [Table 1], it can be seen that the organic light emitting device using the compound having the structure according to the embodiment of the present invention has a lower driving voltage than the organic light emitting device according to the comparative example.

Claims (12)

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

In the [Formula A],
R ₁ to R ₅ are the same or different, and each independently represents hydrogen, deuterium, a substituted or unsubstituted C 1 to C 30 alkyl group, a substituted or unsubstituted C 3 to C 30 cycloalkyl group, a substituted or unsubstituted C 6 to 50 aryl group, substituted or unsubstituted and heteroaryl group having 2 to 50 carbon atoms having O, N or S as a hetero atom, cyano group, nitro group, halogen group, substituted or unsubstituted silyl having 1 to 30 carbon atoms Any one selected from the group,
Hydrogen is bonded to the 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, or any one selected from the following [Structural Formula 1] or [Structural Formula 2],
[Structural Formula 1] [Structural Formula 2]

Hydrogen or deuterium may be bonded to the carbon position of the aromatic ring in the linking group L;
k is an integer from 1 to 5,
l to n are each the same as or different from each other, and each independently an integer of 1 to 4,
o is an integer from 1 to 3,
When k to o are each 2 or more, each of R ₁ to R ₅ are the same as or different from each other,
'***' of X is a binding site that binds to the linking group L,
At least one of the substituents R ₁ to R _{5 includes deuterium,}
Wherein R ₂ and / or R ₃ is deuterium, l is 2 or more, or m is 2 or more,
or R ₄ and/or R ₅ are deuterium, n is 2 or more, or o is 2 or more;
'Substitution' in 'substituted or unsubstituted' in [Formula A] is deuterium, cyano group, halogen group, nitro group, C1-C24 alkyl group, C1-C24 halogenated alkyl group, C6-C6 A group consisting of a 24 aryl group, an arylalkyl group having 6 to 24 carbon atoms, a heteroaryl group having 2 to 24 carbon atoms, a heteroarylalkyl group having 2 to 24 carbon atoms, an alkylsilyl group having 1 to 24 carbon atoms, and an arylsilyl group having 1 to 24 carbon atoms. It means to be substituted with one or more substituents selected from. delete delete The method of claim 1,
The R ₁ is deuterium, k is an organic light emitting compound, characterized in that 5. delete delete The method of claim 1,
The organic light emitting compound is an organic light emitting compound, characterized in that represented by <Compound 136> or <Compound 137>.

<Compound 136><Compound137> a first electrode;
a second electrode opposite 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 of claims 1, 4 and 7. 9. The method of claim 8,
The organic layer comprises 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. 10. The method of claim 9,
An organic light emitting device, characterized in that the organic layer interposed between the first electrode and the second electrode is a light emitting layer, the light emitting layer is made of a host and a dopant, and the organic light emitting compound is used as a host. 10. The method of claim 9,
At least one layer selected from each of the layers is an organic light emitting device, characterized in that it is formed by a deposition process or a solution process. 9. The method of claim 8,
The organic light emitting device may include a flat panel display device; flexible display devices; devices for flat-panel lighting, either monochromatic or white; And, Monochromatic or white flexible lighting device; Organic light emitting device, characterized in that used in any one device selected from.

Images