KR102436175B1 - Novel aromatic compounds for organic light-emitting diode and organic light-emitting diode including the same - Google Patents

Abstract

상기 화학식 A에서 고리그룹 A₁ 내지 A₃, R₁ 내지 R₁₁, L, n 구조식 Q 및 구조식 A'은 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, the ring groups A ₁ to A ₃ , R ₁ to R ₁₁ , L, n Structural formula Q and Structural formula A' are as described in the detailed description of the invention.

Description

Novel aromatic compounds for organic light-emitting diode and organic light-emitting diode including the same

The present invention relates to a novel aromatic organic light emitting compound and an organic light emitting device comprising the same, and more particularly, to a compound for an organic light emitting device having excellent device characteristics such as luminous efficiency when used as a fluorescent host, and an organic light emitting device comprising the same It relates to a light emitting device.

An organic light emitting diode (OLED) is a display using a self-emission 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 and thus a full-color (full-color) display. ) 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 material 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, and may include, 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. When a voltage is applied between the two electrodes in the structure of the organic light emitting device, 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 It lights up when it falls back to the ground state. 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 the 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 the light emission 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 the light emitting material, the maximum emission wavelength moves 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, so that the 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 the 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 can be obtained according to the type of the dopant used.

As a prior art related to a host compound among these light emitting layers, Korean Patent Publication No. 10-1092006 (2011.12.09) discloses an organic light emitting device including an anthracene derivative in which phenyl groups having substituents are bonded to both ends of an anthracene structure in a light emitting medium layer. The technology is described, and in Korean Patent Publication No. 10-2006-0113954 (November 3, 2006), a technology related to an organic light emitting device including an asymmetric anthracene derivative having a specific structure in a light emitting medium layer is described.

However, despite the fact that various types of compounds for use in the light emitting medium layer including the prior art have been prepared, the need for the development of an organic material layer material for an organic light emitting device that is stable, efficient, and has a long lifespan is continuously required. the current situation.

Registered Patent Publication No. 10-1092006 (2011.12.09)

Laid-open Patent Publication No. 10-2006-0113954 (2006.11.03)

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 has excellent device characteristics such as luminous efficiency.

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],

A ₁ to A ₃ are the same or different from each other, and each independently represents a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 carbon atoms, or a substituted or unsubstituted aromatic hetero ring having 2 to 50 carbon atoms;

Two carbon atoms adjacent to each other in the aromatic ring of A ₁ and a carbon atom connected to the substituents R ₁ and R ₂ , and two carbon atoms adjacent to each other in the aromatic ring of A ₂ form a 5-membered ring to form a condensed ring form;

Two carbon atoms adjacent to each other in at least one aromatic ring of A ₁ and A ₂ are bonded to * in the structural formula Q, and two adjacent carbon atoms in the aromatic ring of A ₃ and an oxygen atom in the structural formula Q; and two carbon atoms adjacent to each other in at least one aromatic ring of A ₁ and A ₂ form a condensed ring by forming a 5-membered ring;

one carbon atom in at least one aromatic ring of A ₁ to A ₃ is connected with * in the structural formula A';

The linking group L is a single bond, a substituted or unsubstituted C1-C60 alkylene group, a substituted or unsubstituted C2-C60 Alkenylene group, a substituted or unsubstituted C 2 to C 60 alkynylene group, a substituted or unsubstituted C 3 to C 60 a cycloalkylene group, a substituted or unsubstituted heterocycloalkylene group having 2 to 60 carbon atoms, a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms;

n is an integer of 1 to 3, but when n is 2 or more, each L is the same or different from each other,

said R ₁ to R ₁₁ are the same or different, and are each independently 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 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 An aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylthioxy group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthioxy group having 5 to 30 carbon atoms, or a substituted or unsubstituted alkylamine group having 1 to 30 carbon atoms , 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 heteroaryl group having 2 to 50 carbon atoms and having O, N or S as a heteroatom , cyano group, nitro group, halogen group, substituted or unsubstituted C 1 to C 30 silyl group, substituted or unsubstituted C 1 to C 30 germanium group, substituted or unsubstituted C 1 to C 30 boron group, substituted or an 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, each of which is adjacent to each other It may be connected with a substituent to form an alicyclic, aromatic monocyclic or polycyclic ring, and the carbon atoms of the formed alicyclic, aromatic monocyclic or polycyclic ring may be substituted with any one or more heteroatoms selected from N, S, O. can;

R ₁ and R ₂ may be connected to each other to form a ring.

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 superior luminous efficiency compared to conventional materials, and can be used in the manufacture of stable and excellent devices.

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]

In the [Formula A],

A ₁ to A ₃ are the same or different from each other, and each independently represents a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 carbon atoms, or a substituted or unsubstituted aromatic hetero ring having 2 to 50 carbon atoms;

Two carbon atoms adjacent to each other in the aromatic ring of A ₁ and a carbon atom connected to the substituents R ₁ and R ₂ , and two carbon atoms adjacent to each other in the aromatic ring of A ₂ form a 5-membered ring to form a condensed ring form;

Two carbon atoms adjacent to each other in at least one aromatic ring of A ₁ and A ₂ are bonded to * in the structural formula Q, and two adjacent carbon atoms in the aromatic ring of A ₃ and an oxygen atom in the structural formula Q; and two carbon atoms adjacent to each other in at least one aromatic ring of A ₁ and A ₂ form a condensed ring by forming a 5-membered ring;

one carbon atom in at least one aromatic ring of A ₁ to A ₃ is connected to * in the structural formula A';

The linking group L is a single bond, a substituted or unsubstituted C1-C60 alkylene group, a substituted or unsubstituted C2-C60 Alkenylene group, a substituted or unsubstituted C 2 to C 60 alkynylene group, a substituted or unsubstituted C 3 to C 60 a cycloalkylene group, a substituted or unsubstituted heterocycloalkylene group having 2 to 60 carbon atoms, a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms;

n is an integer of 1 to 3, but when n is 2 or more, each L is the same or different from each other,

said R ₁ to R ₁₁ are the same or different, and are each independently 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 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 An aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylthioxy group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthioxy group having 5 to 30 carbon atoms, or a substituted or unsubstituted alkylamine group having 1 to 30 carbon atoms , 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 heteroaryl group having 2 to 50 carbon atoms and having O, N or S as a heteroatom , cyano group, nitro group, halogen group, substituted or unsubstituted C 1 to C 30 silyl group, substituted or unsubstituted C 1 to C 30 germanium group, substituted or unsubstituted C 1 to C 30 boron group, substituted or an 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, each of which is adjacent to each other It may be connected with a substituent to form an alicyclic, aromatic monocyclic or polycyclic ring, and the carbon atoms of the formed alicyclic, aromatic monocyclic or polycyclic ring may be substituted with any one or more heteroatoms selected from N, S, O. can;

R ₁ and R ₂ may be linked to each other to form a ring;

'Substitution' in 'substituted or unsubstituted' in [Formula A] is deuterium, a cyano group, a halogen group, a hydroxy 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 being 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 substituted by the substituent. For example, a phenyl group substituted with a butyl group at the para position should be regarded as corresponding 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 an "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, and 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 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.

When driving an organic light emitting device employing the compound represented by the formula A in the present invention between a pair of electrodes (anode and cathode), the compound represented by the formula A is a condensation product having a benzofuranyl group in the structural formula Q A structure in which the skeleton structure of the ring and the skeleton structure of the condensed ring by a fluorenyl group including a carbon atom bonded to the substituent R1 and the substituent R2 are connected to each other and the anthracene skeleton structure represented by the Structural Formula A' are connected to each other By the characteristic, it is possible to increase the luminous efficiency of the organic light emitting device.

That is, in the present invention, the luminous efficiency of the organic light emitting diode may be increased by bonding the anthracene skeleton of the structural formula A′ to any one or more of the ring groups A ₁ , A ₂ or A ₃ in the general formula A.

In the present invention, the linking group L in Formula A is a single bond, or any one selected from the following [Structural Formula 1] to [Structural Formula 8], and n may be 1 or 2.

[Structural formula 1] [Structural formula 2] [Structural formula 3] [Structural formula 4]

[Structural formula 5] [Structural formula 6] [Structural formula 7] [Structural formula 8]

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

In addition, the substituents R1 and R2 in Formula A of the present invention may be the same or different from each other and independently of each other, may be a substituted or unsubstituted C6-C24 aryl group.

Also, in the present invention, A1 and A3 may be the same as or different from each other, and independently of each other may be any one selected from the following [Structural Formula 10] to [Structural Formula 18].

[Structural formula 10] [Structural formula 11] [Structural formula 12]

[Structural formula 13] [Structural formula 14] [Structural formula 15]

[Structural formula 16] [Structural formula 17] [Structural formula 18]

In the [Structural Formula 10] to [Structural Formula 18], "-*" is a binding site for forming a 5-membered ring containing carbon atoms connected to the substituents R1 and R2, or a 5-membered ring containing an oxygen atom of Structural Formula Q to form means a binding site for, in the structural formula, R is the same as R ₃ to R ₁₁ as defined above,

m is an integer of 1 to 8, and when m is 2 or more, each R may be the same as or different from each other.

In this case, the ring group A ₂ may be a ring represented by [Structural Formula 10], and R ₇ may be a substituted or unsubstituted aryl group having 6 to 50 carbon atoms.

[Structural formula 10]

Here, R is the same as defined above, and m is an integer of 1 to 3.

Hereinafter, as an embodiment of the organic light emitting compound of the present invention, any one compound selected from the group represented by the following [Formula 1] to [Formula 96] is shown, but the compounds according to the present invention are not limited thereto .

[Formula 1] [Formula 2] [Formula 3]

[Formula 4] [Formula 5] [Formula 6]

[Formula 7] [Formula 8] [Formula 9]

[Formula 10] [Formula 11] [Formula 12]

[Formula 13] [Formula 14] [Formula 15]

[Formula 16] [Formula 17] [Formula 18]

[Formula 19] [Formula 20] [Formula 21]

[Formula 22] [Formula 23] [Formula 24]

[Formula 25] [Formula 26] [Formula 27]

[Formula 28] [Formula 29] [Formula 30]

[Formula 31] [Formula 32] [Formula 33]

[Formula 34] [Formula 35] [Formula 36]

[Formula 37] [Formula 38] [Formula 39]

[Formula 40] [Formula 41] [Formula 42]

[Formula 43] [Formula 44] [Formula 45]

[Formula 46] [Formula 47] [Formula 48]

[Formula 49] [Formula 50] [Formula 51]

[Formula 52] [Formula 53] [Formula 54]

[Formula 55] [Formula 56] [Formula 57]

[Formula 58] [Formula 59] [Formula 60]

[Formula 61] [Formula 62] [Formula 63]

[Formula 64] [Formula 65] [Formula 66]

[Formula 67] [Formula 68] [Formula 69]

[Formula 70] [Formula 71] [Formula 72]

[Formula 73] [Formula 74] [Formula 75]

[Formula 76] [Formula 77] [Formula 78]

[Formula 79] [Formula 80] [Formula 81]

[Formula 82] [Formula 83] [Formula 84]

[Formula 85] [Formula 86] [Formula 87]

[Formula 88] [Formula 89] [Formula 90]

[Formula 91] [Formula 92] [Formula 93]

[Formula 94] [Formula 95] [Formula 96]

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 of the organic light emitting compounds of 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 pyrene compounds, deuterium substituted pyrene compounds, arylamines, deuterium substituted arylamines, peryl compounds, deuterium substituted peryl compounds, pyrrole compounds, 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, 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 the hole injection function and the hole transport function at the same time, the light emitting layer, the electron transport layer and the 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 a monochromatic or white flexible lighting device; may be used in any one device selected from the group consisting of:

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 mainly diamine, triamine or tetraamine derivatives 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) or the like can be used.

A hole injection layer (HIL, Hole Injecting Layer) may be additionally stacked 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, 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 is an oxadiazole derivative etc. can 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 any particular limitation, and for example, a material such as LiF, NaCl, CsF, Li ₂ O, 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, a material for an anode electrode is coated on the substrate 10 to form the anode 20 . 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, 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 as a material for the anode electrode.

A hole injection layer 30 is formed by vacuum thermal deposition 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, or 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 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 light emitting layer has a thickness of 50 to 2,000 Å, and the light emitting layer may consist 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 C5 to C50 aryl group, a substituted or unsubstituted heteroaryl group having O, N or S as a hetero atom, a substituted or unsubstituted C6 to C60 arylene group , 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 , di(substituted or unsubstituted aryl having 6 to 60 carbon atoms) at least one selected from the group consisting of an amino group, Z ₁ to Z ₂ Each may be 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, and 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 as or different from each other, and R ₃ In this plural, each R ₃ may be in a fused form, and n is an integer of 1 to 4.

In addition, the amine group bonded to A in [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]

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

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

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

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

[Substitute 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] [substituent 38] [substituent 39]

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

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

[substituent 46] [substituent 47] [substituent 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 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 unsubstituted C 6 to C 60 aryl group, 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 C1 to C40 alkylsilyl group, a substituted or unsubstituted C6 to C30 arylsilyl group, 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 of ordinary skill in the art that the scope of the present invention is not limited thereby.

(Example)

Synthesis example 1: Synthesis of Formula 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>

9-bromoanthracene (15.0 g, 58 mmol), phenylboronic acid (8.5 g, 70 mol), tetrakis (triphenylphosphine) palladium (2.02 g, 0.18 mmol), potassium carbonate (16.13) in a 250 mL round-bottom flask reactor g, 116.7 mmol) was added, and toluene 75 mL, tetrahydrofuran 75 mL, and water 30 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. (11.0 g, 74.1%)

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

Intermediate 1-b was synthesized according to Scheme 2:

<Scheme 2>

<Intermediate 1-a> <Intermediate 1-b>

<Intermediate 1-a> (11.0 g, 43 mmol) was placed in a 250 ml round-bottom flask, and N,N-dimethylformamide (110 ml) was added thereto and dissolved. N-bromosuccinimide (8.5 g, 48 mmol) was slowly added and stirred at room temperature. After confirming the completion of the reaction by thin layer chromatography, 100 ml of H2O was slowly added to the reaction solution and stirred. After stirring for about 1 hour, the resulting solid was filtered. After sufficiently washing with H2O, dissolved in toluene, filtered through silica gel, and concentrated under reduced pressure, the resulting filtrate was recrystallized from n-hexane to obtain a product (12.0 g, 83.3%).

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>

<Intermediate 1-b> (12.0g, 36mmol) was put in a 250ml round-bottom flask, and 100ml of tetrahydrofuran was added and dissolved. The reaction solution was cooled to -78°C under a nitrogen atmosphere. Normal butyl lithium (24.76ml, 40mmol) was slowly added dropwise to the cooled solution over 30 minutes, and stirred at the same temperature for 1 hour. Trimethylborate (4.5 g, 43 mmol) was added dropwise at the same temperature and stirred at room temperature overnight. The reaction solution was acidified by dropwise addition of 2-N hydrochloric acid, followed by stirring for 1 hour. After extraction with ethyl acetate, the organic layer was separated, concentrated under reduced pressure, and crystallized by adding normal hexane. <Intermediate 1-c> was obtained. (7.5g, 69%)

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

Intermediate 1-d was synthesized according to Scheme 4:

<Scheme 4>

<Intermediate 1-d>

Methyl 5-bromo-2-iodobenzoate (20.0 g, 59 mmol), 4-dibenzoboronic acid (8.5 g, 70 mol), tetrakis (triphenylphosphine) palladium (1.36) in a 500 mL round bottom flask reactor g, 0.12 mmol), potassium carbonate (16.2 g, 117.3 mmol) were added, and toluene 100 mL, tetrahydrofuran 110 mL, and water 40 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 separated by column chromatography to obtain Intermediate 1-d. (15.0 g, 67.1%)

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> (15.0, 39 mmol) and sodium hydroxide (1.89 g, 47 mmol) were put in a 500 mL round-bottom flask reactor, and the mixture was stirred under reflux for 48 hours. After confirming the completion of the reaction by thin layer chromatography, it was cooled to room temperature. To the cooled solution, 2-normal hydrochloric acid was added dropwise and acidified, and the resulting solid was filtered after stirring for 30 minutes. <Intermediate 1-e> was obtained by recrystallization from methylene chloride and n-hexane. (13.5 g, 93.4%)

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>

<Intermediate 1-e> (13.5 g, 37 mmol) and 135 ml of methanesulfonic acid were added to a 250 ml round-bottom flask reactor, the temperature was raised to 80°C, and the mixture was stirred for 3 hours. After confirming the completion of the reaction by thin film chromatography, it was cooled to room temperature. The reaction solution was slowly added dropwise to 150 ml of ice water and stirred for 30 minutes. The resulting solid was filtered and washed with water and methanol. <Intermediate 1-f> was obtained. (11.50 g, 89.6%)

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 250ml round-bottom flask reactor, 2-bromobiphenyl (10.7g, 46mmol) and 120ml of tetrahydrofuran were added and cooled to -78°C in a nitrogen atmosphere. Normal butyl lithium (24.7 ml, 40 mmol) was added dropwise to the cooled reaction solution at the same temperature. After stirring the reaction solution for 2 hours, <Intermediate 1-f> (11.5 g, 33 mmol) was added little by little and stirred at room temperature. When the color of the reaction solution changed, completion of the reaction was confirmed by TLC. 50 ml of H2O was added to complete the reaction, and extraction was performed with ethyl acetate and water. The organic layer was separated, concentrated under reduced pressure, and recrystallized from acetonitrile to obtain <Intermediate 1-g>. (13.6 g, 82%)

Synthesis example 1-(8): Synthesis of Intermediate 1-h

Intermediate 1-h was synthesized according to Scheme 8 below:

<Scheme 8>

<Intermediate 1-g> <Intermediate 1-h>

In a 250ml round-bottom flask reactor, <Intermediate 1-g> (13.6g, 27mmol), 130ml acetic acid, and 2ml sulfuric acid were added and stirred under reflux for 5 hours. When a solid was formed, the reaction was confirmed by thin film chromatography and then cooled to room temperature. The resulting solid was filtered, washed with H 2 O and methanol, dissolved in monochlorobenzene, filtered through silica gel, concentrated and cooled to room temperature to obtain <Intermediate 1-h>. (11.2 g, 85%>

Synthesis example 1-(9): Synthesis of compound 5

Compound 5 was synthesized according to Scheme 9:

<Scheme 9>

<Intermediate 1-h> <Intermediate 1-c> <Compound 5>

<Intermediate 1-h> (5.5g, 11mmol), <Intermediate 1-c> (4.1g, 14mmol), tetrakis(triphenylphosphine)palladium (0.39g, 0.3mmol), Potassium carbonate (3.13 g, 227 mmol) was added, and toluene 30 mL, tetrahydrofuran 30 mL, and water 10 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. The intermediate <Compound 5> was obtained by recrystallization from toluene and acetone. (3.2 g, 42.9%)

MS (MALDI-TOF): m/z 658.23 [M ⁺ ]

Synthesis example 2: Synthesis of Formula 28

Synthesis example 2-(1): Synthesis of Intermediate 2-a

Intermediate 2-a was synthesized according to Scheme 10:

<Scheme 10>

<Intermediate 2-a>

<Intermediate 2-a> (14 g) using the same method except that 1,2-dibromobenzene was used instead of methyl 5-bromo-2-iodobenzoate in Synthesis Example 1-(4) , 68% ) was obtained.

Synthesis example 2-(2): Synthesis of Intermediate 2-b

Intermediate 2-b was synthesized according to Scheme 11 below:

<Scheme 11>

<Intermediate 1-f> <Intermediate 2-a> <Intermediate 2-b>

<Intermediate 2-b> (12 g, 65%) was obtained in the same manner as in Synthesis Example 1-(7), except that <Intermediate 2-a> was used instead of 2-bromobiphenyl.

Synthesis example 2-(3): Synthesis of Intermediate 2-c

Intermediate 2-c was synthesized according to Scheme 12:

<Scheme 12>

<Intermediate 2-b> <Intermediate 2-c>

<Intermediate 2-c> (10 g, 85.9%) was obtained in the same manner as in Synthesis Example 1-(8), except that <Intermediate 2-b> was used instead of <Intermediate 1-g>.

Synthesis example 2-(4): Synthesis of compound 28

Compound 28 was synthesized according to Scheme 13 below:

<Scheme 13>

<Intermediate 2-c> <Intermediate 1-c> <Compound 28>

<Compound 28> (2.3 g, 30.8% ) was obtained in the same manner except that <Intermediate 2-c> was used instead of <Intermediate 1-h> in Synthesis Example 1-(9).

MS (MALDI-TOF): m/z 748.2 [M ⁺ ]

Synthesis example 3: Synthesis of Formula 44

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

Intermediate 3-a was synthesized according to Scheme 14 below:

<Scheme 14>

<Intermediate 3-a>

In a 2L round-bottom flask reactor, 1-hydroxy 2-naphthalic acid (50 g, 266 mmol), methanol 1000 ml, and sulfuric acid 100 ml were added and stirred under reflux for 100 hours. After confirming the completion of the reaction by TLC, it was cooled to room temperature. The solution was concentrated under reduced pressure and extracted with dichloromethane and water. The organic layer was separated, concentrated under reduced pressure, and crystallized by adding an excess of heptane to obtain <Intermediate 3-a> (40 g, 74.4%).

Synthesis example 3-(2): Synthesis of Intermediate 3-b

Intermediate 3-b was synthesized according to Scheme 15:

<Scheme 15>

<Intermediate 3-a> <Intermediate 3-b>

<Intermediate 3-a> (40 g, 198 mmol) and 400 ml of acetic acid were placed in a 1L round-bottom flask reactor and stirred at room temperature. Bromine (12.16ml, 237mmol) was diluted in 80ml of acetic acid and added dropwise to the reaction solution. The reaction solution was stirred at room temperature for 5 hours. After confirming the completion of the reaction by TLC, filtration was performed, and <Intermediate 3-b> (50 g, 89%) was obtained after a heptane slurry.

Synthesis example 3-(3): Synthesis of Intermediate 3-c

Intermediate 3-c was synthesized according to Scheme 16 below:

<Scheme 16>

<Intermediate 3-b> <Intermediate 3-c>

<Intermediate 3-b> (50g, 178mmol) and dichloromethane were added to a 2L round-bottom flask reactor and stirred. Pyridine (28.1 g, 356 mmol) was added to the reaction solution in a nitrogen atmosphere and stirred at room temperature for 20 minutes. After the reaction solution was cooled to 0 degrees, trifluoromethanesulfonic anhydride (65.24 g, 231 mmol) was added dropwise in a nitrogen atmosphere. After stirring for 3 hours, completion of the reaction was confirmed by TLC, 10 ml of water was added, and the mixture was stirred for 10 minutes. The reaction solution was concentrated under reduced pressure, followed by column separation to obtain <Intermediate 3-c> (40 g, 54%).

Synthesis example 3-(4): Synthesis of intermediate 3-d

Intermediate 3-d was synthesized according to Scheme 17 below:

<Scheme 17>

<Intermediate 3-c> <Intermediate 3-d>

<Intermediate 3-d> (19 g, 45) using the same method except that <Intermediate 3-c> was used instead of methyl 5-bromo-2-iodobenzoate in Synthesis Example 1-(4) %) was obtained.

Synthesis example 3-(5): Synthesis of Intermediate 3-e

Intermediate 3-e was synthesized according to Scheme 18:

<Scheme 18>

<Intermediate 3-d> <Intermediate 3-e>

<Intermediate 3-e> (15 g, 81.6% ) was obtained in the same manner as in Synthesis Example 1-(5), except that <Intermediate 3-d> was used instead of <Intermediate 1-d>.

Synthesis example 3-(6): Synthesis of Intermediate 3-f

Intermediate 3-f was synthesized according to Scheme 19 below:

<Scheme 19>

<Intermediate 3-e> <Intermediate 3-f>

<Intermediate 3-f> (11.6 g, 67.4% ) was obtained in the same manner except that <Intermediate 3-e> was used instead of <Intermediate 1-e> in Synthesis Example 1-(6).

Synthesis example 3-(7): Synthesis of intermediate 3-g

Intermediate 3-g was synthesized according to Scheme 20:

<Scheme 20>

<Intermediate 3-f> <Intermediate 3-g>

<Intermediate 3-g> (13 g, 80% ) was obtained in the same manner except that <Intermediate 3-f> was used instead of <Intermediate 1-f> in Synthesis Example 1-(7).

Synthesis example 3-(8): Synthesis of Intermediate 3-h

Intermediate 3-h was synthesized according to Scheme 21:

<Scheme 21>

<Intermediate 3-g> <Intermediate 3-h>

<Intermediate 3-h> (5.2 g, 41% ) was obtained in the same manner except that <Intermediate 3-g> was used instead of <Intermediate 1-g> in Synthesis Example 1-(8).

Synthesis example 3-(9): Synthesis of compound 44

Compound 44 was synthesized according to Scheme 22:

<Scheme 22>

<Intermediate 3-h> <Compound 44>

In Synthesis Example 1-(9), <Intermediate 3-h> instead of <Intermediate 1-h> and 9-(2-naphthyl)anthracene 10-boronic acid were used instead of <Intermediate 1-c> in Synthesis Example 1-(9). <Compound 44> (52.1 g, 57% ) was obtained by using the method.

MS (MALDI-TOF): m/z 758.2 [M ⁺ ]

Synthesis example 4: Synthesis of Formula 51

Synthesis example 4-(1): Synthesis of Intermediate 4-a

Intermediate 4-a was synthesized according to Scheme 23:

<Scheme 23>

<Intermediate 4-a>

<Intermediate 4-a> (12 g, 75% ) was obtained in the same manner as in Synthesis Example 1-(1), except that 4-methylphenylboronic acid was used instead of phenylboronic acid.

Synthesis example 4-(2): Synthesis of Intermediate 4-b

Intermediate 4-b was synthesized according to Scheme 24:

<Scheme 24>

<Intermediate 4-a> <Intermediate 4-b>

<Intermediate 4-b> (12 g, 76% ) was obtained in the same manner except that <Intermediate 4-a> was used instead of <Intermediate 1-a> in Synthesis Example 1-(2).

Synthesis example 4-(3): Synthesis of Intermediate 4-c

Intermediate 4-c was synthesized according to Scheme 25:

<Scheme 25>

<Intermediate 4-b> <Intermediate 4-c>

<Intermediate 4-c> (7.5 g, 70% ) was obtained in the same manner except that <Intermediate 4-b> was used instead of <Intermediate 1-b> in Synthesis Example 1-(3).

Synthesis example 4-(4): Synthesis of intermediate 4-d

Intermediate 4-d was synthesized according to Scheme 26:

<Scheme 26>

<Intermediate 4-d>

In a 2L round-bottom flask reactor, 4-bromodibenzofuran (100 g, 0.405 mol), (1R, 2R)-cyclohexane-1,2-diamine (46.21 g, 0.404 mol), acetamide (71.7 g, 1.21 mol) , copper (I) iodide (77.08 g, 0404 mol), potassium carbonate (200 g, 0.809 mol), and 1000 ml of toluene were added and stirred under reflux overnight. After the reaction was completed, it was filtered through a pad of celite and washed with ethyl acetate. The filtrate was extracted with water and ethyl acetate to separate the organic layer. The organic layer was filtered and concentrated under reduced pressure after anhydrous treatment with magnesium sulfate. The material was recrystallized from dichloromethane and petroleum ether to obtain <Intermediate 4-d> (50 g, 32%).

Synthesis example 4-(5): Synthesis of Intermediate 4-e

Intermediate 4-e was synthesized according to Scheme 27 below:

<Scheme 27>

<Intermediate 4-d> <Intermediate 4-e>

<Intermediate 4-d> (50 g, 0.222 mol) and 600 ml of acetic acid were dissolved in a 2L round-bottom flask reactor and stirred at room temperature. Bromine (11.37 ml, 0.222 mol) was diluted in 200 ml of acetic acid and added dropwise to the reaction solution, followed by stirring for 4 hours. After the reaction was completed, the resulting solid was filtered and washed with water. The solid was dissolved in 1000 ml of a tetrahydrofuran/water/ethanol ratio 1:1:1 solution, potassium hydroxide (250g, 1.11mol) was added, and the mixture was stirred under reflux overnight. After completion of the reaction, the solvent was concentrated under reduced pressure and extracted with ethyl acetate and water. The organic layer was separated, anhydrous treatment with magnesium sulfate, filtered, and concentrated under reduced pressure. It was recrystallized from ethyl acetate and heptane to obtain <Intermediate 4-e> (40 g, 68.7%).

Synthesis example 4-(6): Synthesis of intermediate 4-f

Intermediate 4-f was synthesized according to Scheme 28 below:

<Scheme 28>

<Intermediate 4-e> <Intermediate 4-f>

<Intermediate 4-e> (40 g, 0.153 mol), bis (pinacolato) diboron (51.67 g, 0.183 mol), and 400 ml of acetonitrile were placed in a 1L round-bottom flask reactor and stirred at room temperature. To the reaction solution, tertiary-butylnitrile (26.2g, 0229mol) was added little by little, the temperature was raised, and the mixture was stirred at 80°C for 2 hours. After completion of the reaction, it was cooled to room temperature. The reaction solution was concentrated under reduced pressure and separated by column chromatography to obtain <Intermediate 4-f> (20 g, 35%).

Synthesis example 4-(7): Synthesis of intermediate 4-g

Intermediate 4-g was synthesized according to Scheme 29 below:

<Scheme 29>

<Intermediate 4-f> <Intermediate 4-g>

In Synthesis Example 1-(4), methyl 2-bromobenzoate instead of methyl 5-bromo-2-iodobenzoate, and <Intermediate 4-f> instead of 4-dibenzoboronic acid were used, except that <Intermediate 4-g> (12 g, 67%) was obtained using the method.

Synthesis example 4-(8): Synthesis of intermediate 4-h

Intermediate 4-h was synthesized according to Scheme 30:

<Scheme 30>

<Intermediate 4-g> <Intermediate 4-h>

In Synthesis Example 1-(5), <Intermediate 4-g> (10 g, 86% ) was obtained in the same manner except that <Intermediate 4-g> was used instead of <Intermediate 1-d>.

Synthesis example 4-(9): Synthesis of intermediate 4-i

Intermediate 4-i was synthesized according to Scheme 31 below:

<Scheme 31>

<Intermediate 4-h> <Intermediate 4-i>

<Intermediate 4-i> (8.4 g, 88% ) was obtained in the same manner except that <Intermediate 4-h> was used instead of <Intermediate 1-e> in Synthesis Example 1-(6).

Synthesis example 4-(10): Synthesis of intermediate 4-j

Intermediate 4-j was synthesized according to Scheme 32 below:

<Scheme 32>

<Intermediate 4-i> <Intermediate 4-j>

In Synthesis Example 1-(7), <Intermediate 4-j> (8g, 66%) was obtained by using the same method, except that <Intermediate 4-i> was used instead of <Intermediate 1-f>.

Synthesis example 4-(11): Synthesis of intermediate 4-k

Intermediate 4-k was synthesized according to Scheme 33:

<Scheme 33>

<Intermediate 4-j> <Intermediate 4-k>

In Synthesis Example 1-(8), <Intermediate 4-k> (5.8 g, 74%) was obtained by using the same method, except that <Intermediate 4-j> was used instead of <Intermediate 1-g>.

Synthesis example 4-(11): Synthesis of compound 51

Compound 51 was synthesized according to Scheme 34:

<Scheme 34>

<Intermediate 4-k> <Intermediate 4-c> <Compound 51>

<Compound 51> using the same method except for using <Intermediate 4-k> instead of <Intermediate 1-h> and <Intermediate 4-c> instead of <Intermediate 1-c> in Synthesis Example 1-(9) > (2.8 g, 34% ) was obtained.

MS (MALDI-TOF): m/z 672.2 [M ⁺ ]

Synthesis example 5: Synthesis of Formula 75

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

Intermediate 5-a was synthesized according to Scheme 35:

<Scheme 35>

<Intermediate 5-a>

<Intermediate 5-a> (13 g, 64% ) was obtained in the same manner as in Synthesis Example 1-(1), except that 4-dibenzofuranboronic acid was used instead of phenylboronic acid.

Synthesis example 5-(2): Synthesis of Intermediate 5-b

Intermediate 5-b was synthesized according to Scheme 36 below:

<Scheme 36>

<Intermediate 5-a> <Intermediate 5-b>

<Intermediate 5-b> (14 g, 87%) was obtained in the same manner except that <Intermediate 5-a> was used instead of <Intermediate 1-a> in Synthesis Example 1-(2)

Synthesis example 5-(3): Synthesis of Intermediate 5-c

Intermediate 5-c was synthesized according to Scheme 37 below:

<Scheme 37>

<Intermediate 5-b> <Intermediate 5-c>

<Intermediate 5-c> (7 g, 63%) was obtained by using the same method, except that <Intermediate 5-b> was used instead of <Intermediate 1-b> in Synthesis Example 1-(3)

Synthesis example 5-(4): Synthesis of compound 75

Compound 75 was synthesized according to Scheme 38:

<Scheme 38>

<Intermediate 1-h> <Intermediate 5-c> <Compound 75>

<Compound 75> (3 g, 35%) was obtained in the same manner as in Synthesis Example 1-(9), except that <Intermediate 5-c> was used instead of <Intermediate 1-c>. MS (MALDI-TOF): m/z 748.2 [M ⁺ ]

Synthesis example 6: Synthesis of Formula 76

Synthesis example 6-(1): Synthesis of intermediate 6-a

Intermediate 6-a was synthesized according to Scheme 39:

<Scheme 39>

<Intermediate 6-a>

1-bromo-4-fluorobenzene (25 g, 0.143 mol) and 400 ml of tetrahydrofuran were placed in a 1L round-bottom flask reactor, and the mixture was cooled and stirred at -78°C in a nitrogen atmosphere. Normal butyl lithium (98.2ml, 0.157mol) was added dropwise to the cooled reaction solution, followed by stirring at the same temperature for 1 hour. Trimethylborate (18.8 g, 0.171 mol) was added dropwise followed by stirring at room temperature overnight. After completion of the reaction, 2-normal hydrochloric acid was added dropwise to acidify and stirred for 1 hour. After extraction with ethyl acetate and water, the organic layer was separated and concentrated under reduced pressure. The material was recrystallized from ethyl acetate and heptane to obtain <Intermediate 6-a> (12 g, 60%).

Synthesis example 6-(2): Synthesis of intermediate 6-b

Intermediate 6-b was synthesized according to Scheme 40:

<Scheme 40>

<Intermediate 6-a> <Intermediate 6-b>

Except for using 1,2-dibromobenzene instead of methyl 5-bromo-2-iodobenzoate in Synthesis Example 1-(4) and <Intermediate 6-a> instead of 4-dibenzofuran boronic acid , to obtain <Intermediate 6-b> (10 g, 71%) using the same method.

Synthesis example 6-(3): Synthesis of intermediate 6-c

Intermediate 6-c was synthesized according to Scheme 41:

<Scheme 41>

<Intermediate 1-f> <Intermediate 6-b> <Intermediate 6-c>

<Intermediate 6-c> (9.0 g, 60%) was obtained by using the same method except that <Intermediate 6-b> was used instead of 2-bromobiphenyl in Synthesis Example 1-(7)

Synthesis example 6-(4): Synthesis of intermediate 6-d

Intermediate 6-d was synthesized according to Scheme 42:

<Scheme 42>

<Intermediate 6-c> <Intermediate 6-d>

<Intermediate 6-d> (6.0 g, 69%) was obtained in the same manner except that <Intermediate 6-c> was used instead of <Intermediate 1-g> in Synthesis Example 1-(8).

Synthesis example 6-(5): Synthesis of compound 76

Compound 76 was synthesized according to the following Scheme 43

<Scheme 43>

<Intermediate 6-d> <Intermediate 1-c> <Compound 76>

<Compound 76> (3 g, 39%) was obtained in the same manner except that <Intermediate 6-d> was used instead of <Intermediate 1-h> in Synthesis Example 1-(9).

MS (MALDI-TOF): m/z 676.2 [M ⁺ ]

Synthesis example 7: Synthesis of Formula 91

Synthesis example 7-(1): Synthesis of intermediate 7-a

Intermediate 7-a was synthesized according to Scheme 44 below.

<Scheme 44>

<Intermediate 7-a>

4-dibenzoboronic acid (85.0 g, 0.401 mol), bismuth (III) nitrate pentahydrate (99.2 g, 0.200 mol), and 400 ml of toluene were placed in a 1L round-bottom flask reactor, and the mixture was stirred in a nitrogen atmosphere at 70°C for 3 hours. After completion of the reaction, the mixture was cooled to room temperature and the resulting solid was filtered. After washing with toluene, <Intermediate 7-a> (61.5 g, 72%) was obtained.

Synthesis example 7-(2): Synthesis of intermediate 7-b

Intermediate 7-b was synthesized according to Scheme 45 below.

<Scheme 45>

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

Ethylcyanoacetate (202.9g, 1.794mol) and 500ml of dimethylformamide were placed in a 2L round-bottom flask reactor. Potassium hydroxide (67.10g, 1.196mol) and potassium cyanide (38.95g, 0.598mol) were added, 200ml of dimethylformamide was added, and the mixture was stirred at room temperature. After adding <Intermediate 7-a> (127.5 g, 0.737 mol) little by little to the reaction solution, it was stirred at 50°C for 72 hours. After completion of the reaction, 200 ml of an aqueous sodium hydroxide solution (25%) was added and stirred under reflux. After stirring for 3 hours, it was cooled to room temperature, and extracted with ethyl acetate and water. The organic layer was separated, concentrated under reduced pressure, and separated and purified by column chromatography to obtain <Intermediate 7-b> (20.0 g, 16%).

Synthesis example 7-(3): Synthesis of intermediate 7-c

Intermediate 7-c was synthesized according to Scheme 46 below.

<Scheme 46>

<Intermediate 7-b> <Intermediate 7-c>

<Intermediate 7-b> (20.0 g, 0.096 mol), 600 ml of ethanol, and 170 ml of an aqueous potassium hydroxide solution (142.26 g, 2.53 mol) were placed in a 2L round-bottom flask reactor, and the mixture was stirred under reflux for 12 hours. When the reaction was completed, it was cooled to room temperature. 400 ml of 6N hydrochloric acid was added to the reaction solution for acidification, and the resulting solid was stirred for 20 minutes and then filtered. After washing the solid with ethanol, <Intermediate 7-c> (17.0 g, 88.5%) was obtained.

Synthesis example 7-(4): Synthesis of intermediate 7-d

Intermediate 7-d was synthesized according to Scheme 47 below.

<Scheme 47>

<Intermediate 7-c> <Intermediate 7-d>

<Intermediate 7-c> (17.0 g, 0.075 mol) and 15 ml of sulfuric acid were put in a 2L round-bottom flask reactor, and the mixture was stirred under reflux for 72 hours. After completion of the reaction, the mixture was cooled to room temperature and extracted with ethyl acetate and water. The organic layer was separated and washed with an aqueous sodium hydrogen carbonate solution. An excess of methanol was added to the organic layer during concentration under reduced pressure, and the resulting solid was filtered to obtain <Intermediate 7-d> (14.0 g, 77.6%).

Synthesis example 7-(5): Synthesis of intermediate 7-e

Intermediate 7-e was synthesized according to Scheme 48 below.

<Scheme 48>

<Intermediate 7-d> <Intermediate 7-e>

<Intermediate 7-d> (14.0 g, 0.058 mol), 20 ml of hydrochloric acid, and 100 ml of water were added to a 500 mL round-bottomed flask reactor, cooled to 0°C, and stirred for 1 hour. At the same temperature, 50 ml of an aqueous sodium nitrite (7.4 g, 0.116 mol) solution was added dropwise to the reaction solution, followed by stirring for 1 hour. When 100 ml of an aqueous solution of potassium iodide (30.0 g, 0.180 mol) was added dropwise, it was added dropwise, being careful not to let the temperature of the reaction solution exceed 5 degrees. After stirring at room temperature for 5 hours, after completion of the reaction, the mixture was washed with an aqueous sodium thiosulfate solution and extracted with ethyl acetate and water. The organic layer was separated and concentrated under reduced pressure, followed by separation and purification by column chromatography to obtain <Intermediate 7-e> (9.1 g, 48%).

Synthesis example 7-(6): Synthesis of intermediate 7-f

Intermediate 7-f was synthesized according to Scheme 49 below.

<Scheme 49>

<Intermediate 7-e> <Intermediate 7-f>

Methyl 5-bromo-2-iodobenzoate (9.3 g, 25 mmol), 4-dibenzoboronic acid (8.3 g, 28 mmol), tetrakis (triphenylphosphine) palladium (0.6 g) in a 250 mL round-bottom flask reactor , 0.05mmol), potassium carbonate (6.7g, 50mmol) were added, toluene 50mL, tetrahydrofuran 50mL, and water 20mL. The temperature of the reactor was raised to 80 degrees and stirred for 10 hours. 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 7-f> (5.3 g, 52.3%).

Synthesis example 7-(7): Synthesis of intermediate 7-g

Intermediate 7-g was synthesized according to Scheme 50 below.

<Scheme 50>

<Intermediate 7-f> <Intermediate 7-g>

Bromobenzene (25.5 g, 0.163 mol) and 170 ml of tetrahydrofuran were added to a 500 ml round-bottom flask reactor and cooled to -78°C in a nitrogen atmosphere. Normal butyl lithium (1.6M) (95.6 ml, 0.153 mol) was added dropwise to the cooled reaction solution. After stirring at the same temperature for 1 hour, <Intermediate 7-f> (20.0 g, 0.051 mol) was added, followed by stirring at room temperature for 3 hours. After completion of the reaction, 50 ml of water was added and stirred for 30 minutes. After extraction with ethyl acetate and water, the organic layer was separated and concentrated under reduced pressure. 200 ml of acetic acid and 1 ml of hydrochloric acid were added to the concentrated material, and the temperature was raised to 80 degrees and stirred. After completion of the reaction, it was cooled to room temperature and the resulting solid was filtered. After washing with methanol, <Intermediate 7-g> (20.0 g, 78%) was obtained.

Synthesis example 7-(8): Synthesis of intermediate 7-h

Intermediate 7-h was synthesized according to Scheme 51 below.

<Scheme 51>

<Intermediate 7-g> <Intermediate 7-h>

In a 100mL round-bottom flask reactor, <Intermediate 7-g> (5.5g, 11mmol>, 40ml of dichloromethane was added and stirred at room temperature. Bromine (0.4ml, 8mmol) was diluted in 10ml of dichloromethane and added dropwise, followed by stirring at room temperature for 8 hours. After completion of the reaction, 20 ml of acetone was added to the reaction vessel and stirred. The resulting solid was filtered and washed with acetone. The solid was recrystallized from monochlorobenzene to obtain <Intermediate 7-h> (1.9 g, 30%).

Synthesis example 7-(9): Synthesis of intermediate 7-i

Intermediate 7-i was synthesized according to Scheme 52 below.

<Scheme 52>

<Intermediate 7-i>

<Intermediate 7-i> (6.6 g) using the same method except that 9-(4-bromophenyl)-10-phenylanthracene was used instead of <Intermediate 1-b> in Synthesis Example 1-(3) , 72%) was obtained.

Synthesis example 7-(10): Synthesis of compound 91

Compound 91 was synthesized according to Scheme 53 below.

<Scheme 53>

<Intermediate 7-h> <Intermediate 7-i> <Compound 91>

<Compound 91> was used in the same manner as in Synthesis Example 1-(9), except that <Intermediate 7-h> was used instead of <Intermediate 1-h> and <Intermediate 7-i> was used instead of <Intermediate 1-c> > (3.5 g, 37%).

MS (MALDI-TOF): m/z 826.29 [M+]

Example 1 to 7: Preparation of organic light emitting device

After patterning so that the light emitting area of the ITO glass is 2mm × 2mm in size, it was washed. After the ITO glass was mounted in a vacuum chamber, the base pressure was set to 1×10 ^-6 torr, and then a film was formed on the ITO in the order of DNTPD (700 Å), α-NPD (300 Å), and then the compound according to the present invention ( Compounds 5, 28, 44, 51, 75, 76, 91) and [BD1] 3% were mixed to form a film (250 Å), followed by Alq ₃ (350 Å), LiF (5 Å), Al (1000 Å) An organic light emitting diode was manufactured by forming a film in the order of The emission characteristics of the organic electroluminescent device were measured at 0.4 mA. The structures of [DNTPD], [α-NPD], [BD1], and [Alq ₃ ] are as follows.

[DNTPD] [α-NPD]

[BD1] [Alq_{3 ]}

[BD1] [Alq _{3 ]}

comparative example 1 to 2

It was prepared in the same manner except that BH1 and BH2, which are generally used as fluorescent host materials, were used instead of the compound used in Example 1, and the structures of BH1 and BH2 are as follows.

<BH1><BH2>

For the organic electroluminescent devices manufactured according to Examples 1 to 6 and Comparative Examples 1 to 2, voltage, luminance, and color coordinates were measured, and the results are shown in [Table 1] below.

division host dopant V CD /m ² CIEx CIEy Comparative Example 1 BH1 BD1 4.3 550 0.14 0.12 Comparative Example 2 BH2 BD1 4.2 530 0.14 0.11 Example 1 compound 5 BD1 3.8 770 0.138 0.12 Example 2 compound 28 BD1 3.8 786 0.137 0.12 Example 3 compound 44 BD1 3.8 767 0.134 0.12 Example 4 compound 51 BD1 3.8 759 0.134 0.12 Example 5 compound 75 BD1 3.8 779 0.136 0.12 Example 6 compound 76 BD1 3.8 780 0.135 0.12 Example 7 compound 91 BD1 3.8 778 0.138 0.12

As shown in the evaluation results of [Table 1], the organic light emitting device using the compound of the new structure according to the embodiment of the present invention compared to the comparative example of the organic light emitting device using the compound of the new structure according to the embodiment of the present invention. It can be seen that the driving voltage is low and the luminance is better.

Claims (11)

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

In the [Formula A],
A ₁ to A ₃ are the same or different from each other, and each independently represent a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 carbon atoms;
Two carbon atoms adjacent to each other in the aromatic ring of A1, a carbon atom connected to the substituents R ₁ and R ₂ , and two carbon atoms adjacent to each other in the aromatic ring of A ₂ form a 5-membered ring to form a condensed ring form;
In the [Formula A], the remaining substituents except for A1 to A3 are defined as i) or ii) below.
i) Two carbon atoms adjacent to each other in one aromatic ring of A ₁ and A ₂ are bonded to * in the structural formula Q, and two adjacent carbon atoms in the aromatic ring of A ₃ and an oxygen atom in the structural formula Q , and two carbon atoms adjacent to each other in at least one aromatic ring of A ₁ and A ₂ form a condensed ring by forming a 5-membered ring;
one carbon atom in one aromatic ring of A ₁ to A ₃ is connected to * in the structural formula A';
The linking group L is a single bond or a substituted or unsubstituted arylene group having 6 to 60 carbon atoms;
n is an integer of 1 to 3, but when n is 2 or more, each L is the same as or different from each other,
Wherein R ₃ To R ₁₁ are the same or different, and are each independently 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 Any one selected from an aryl group having 6 to 50 carbon atoms, a cyano group, a nitro group, a halogen group, and a substituted or unsubstituted silyl group having 1 to 30 carbon atoms,
Substituents R ₁ and R ₂ are the same or different from each other and are each independently a substituted or unsubstituted C6-C24 aryl group,
R ₁ and R ₂ are connected to each other to form a ring,

ii) two carbon atoms adjacent to each other in each aromatic ring of A ₁ and A ₂ are bonded to * in the structural formula Q, and two adjacent carbon atoms in the aromatic ring of A ₃ and an oxygen atom in the structural formula Q; and two carbon atoms adjacent to each other in at least one aromatic ring of A ₁ and A ₂ form a condensed ring by forming a 5-membered ring;
one carbon atom in one aromatic ring of A ₁ to A ₃ is connected to * in the structural formula A';
The linking group L is a single bond or a substituted or unsubstituted arylene group having 6 to 60 carbon atoms;
n is an integer of 1 to 3, but when n is 2 or more, each L is the same as or different from each other,
Wherein R ₃ To R ₁₁ are the same or different, and are each independently 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 Any one selected from an aryl group having 6 to 50 carbon atoms, a cyano group, a nitro group, a halogen group, and a substituted or unsubstituted silyl group having 1 to 30 carbon atoms,
Substituents R ₁ and R ₂ are the same or different and are each independently a substituted or unsubstituted C6-C24 aryl group, a substituted or unsubstituted C1-C30 alkyl group, and a substituted or unsubstituted C3-C30 aryl group. selected from the cycloalkyl group of
'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 Substituted with one or more substituents selected from the group consisting of a to 24 aryl group, an arylalkyl group having 6 to 24 carbon atoms, a heteroaryl 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. means to be The method of claim 1,
The linking group L is a single bond, or any one selected from the following [Structural Formula 1], [Structural Formula 2], [Structural Formula 4], [Structural Formula 6] and [Structural Formula 7],
n is 1 or 2, characterized in that the organic light emitting compound.
[Structural formula 1] [Structural formula 2] [Structural formula 4]

[Structural formula 6] [Structural formula 7]

Hydrogen or deuterium may be bonded to the carbon site of the aromatic ring in the linking group L. The method of claim 1,
ii) two carbon atoms adjacent to each other in each aromatic ring of A ₁ and A ₂ are bonded to * in the structural formula Q, and two adjacent carbon atoms in the aromatic ring of A ₃ and an oxygen atom in the structural formula Q; and two carbon atoms adjacent to each other in at least one aromatic ring of A ₁ and A ₂ form a condensed ring by forming a 5-membered ring; When one carbon atom in one aromatic ring of A ₁ to A ₃ is connected to * in the structural formula A',
Substituents R ₁ and R ₂ in Formula A are each the same or different and independently of each other, an organic light emitting compound, characterized in that it is a substituted or unsubstituted aryl group having 6 to 24 carbon atoms. The method of claim 1,
The A ₁ to A ₃ are the same as or different from each other, and independently of each other, an organic light emitting compound, characterized in that any one selected from the following [Structural Formula 10] to [Structural Formula 18].
[Structural formula 10] [Structural formula 11] [Structural formula 12]

[Structural formula 13] [Structural formula 14] [Structural formula 15]

[Structural formula 16] [Structural formula 17] [Structural formula 18]

In the [Structural Formula 10] to [Structural Formula 18], "-*" forms a 5-membered ring including a binding site or an oxygen atom of Structural Formula Q for forming a 5-membered ring including carbon atoms connected to the substituents R ₁ and R ₂ It means a binding site for, in the structural formula R is the same as R ₃ to R ₁₁ as defined in claim 1,
m is an integer of 1 to 8, and when m is 2 or more, each R may be the same as or different from each other. 5. The method of claim 4,
A ₂ is a ring represented by [Structural Formula 10],
R ₇ is an organic light-emitting compound, characterized in that a substituted or unsubstituted aryl group having 6 to 50 carbon atoms.
[Structural formula 10]

Wherein R is the same as defined in claim 4,
m is an integer from 1 to 3. The method of claim 1,
The organic light emitting compound is the following [Formula 1] to [Formula 13], [Formula 15] to [Formula 17], [Formula 25], [Formula 30] to [Formula 53], [Formula 55], [Formula 56 ], [Formula 65], [Formula 70] to [Formula 74], [Formula 76], [Formula 77], [Formula 89], [Formula 91] to [Formula 93], [Formula 95] and [Formula 96] ] An organic light-emitting compound, characterized in that any one selected from the group represented by.
[Formula 1] [Formula 2] [Formula 3]

[Formula 4] [Formula 5] [Formula 6]

[Formula 7] [Formula 8] [Formula 9]

[Formula 10] [Formula 11] [Formula 12]

[Formula 13] [Formula 15]

[Formula 16] [Formula 17]

[Formula 25] [Formula 30]

[Formula 31] [Formula 32] [Formula 33]

[Formula 34] [Formula 35] [Formula 36]

[Formula 37] [Formula 38] [Formula 39]

[Formula 40] [Formula 41] [Formula 42]

[Formula 43] [Formula 44] [Formula 45]

[Formula 46] [Formula 47] [Formula 48]

[Formula 49] [Formula 50] [Formula 51]

[Formula 52] [Formula 53]

[Formula 55] [Formula 56]

[Formula 65]

[Formula 70] [Formula 71] [Formula 72]

[Formula 73] [Formula 74]

[Formula 76] [Formula 77]

[Formula 89]

[Formula 91] [Formula 92] [Formula 93]

[Formula 95] [Formula 96]

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 to 6. 8. The method of claim 7,
The organic layer comprises 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. 9. The method of claim 8,
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 consists of a host and a dopant, and the organic light emitting compound is used as a host. 9. The method of claim 8,
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. 8. The method of claim 7,
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.

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