KR20140008024A - Aromatic compound and organic light-emitting diode comprising the compound - Google Patents

Abstract

The present invention relates to a novel aromatic compound and an organic electroluminescent device comprising the compound. The organic electroluminescent device comprising the aromatic compound of the present invention has low driving voltage, excellent light emitting properties including brightness, high thermal stability, and long lifetime. The organic electroluminescent device includes an anode, a cathode, and a layer containing the aromatic compound in between the anode and cathode.

Description

Aromatic compound and organic light-emitting diode comprising the compound

The present invention relates to a novel aromatic compound that can be used as a light emitting layer material and an organic light emitting device including the same, and more particularly, low driving voltage, excellent light emission characteristics such as luminance, high thermal stability and long life It relates to a compound and an organic light emitting device comprising the same.

Recently, the organic light emitting device capable of low voltage driving with self-luminous type has better viewing angle, contrast ratio, and requires no backlight, light weight, thinness, and consumption compared to the liquid crystal display (LCD) which is the mainstream of flat panel display devices. It is advantageous in terms of power and is attracting attention as a next generation display device due to its wide color reproduction range.

Organic light emitting diodes (OLEDs) emit light by injecting charges into the organic light emitting layer formed between the electron injection electrode (cathode) and the hole injection electrode (anode) and then disappear after pairing electrons and holes. to be.

An organic electroluminescent device using an organic light emitting phenomenon usually has a structure including an anode, an anode, and an organic material layer therebetween. Here, in order to increase the efficiency and stability of the organic electroluminescent device, the organic material layer may have a multi-layer structure composed of different materials and may include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, . When a voltage is applied between two electrodes in the structure of the organic light emitting device, holes are injected into the organic material layer at the anode and electrons are injected into the organic material layer, and excitons are formed when the injected holes meet the electrons. When it falls back to the ground, it glows.

Organic electroluminescent devices can not only form devices on flexible transparent substrates such as plastics, but also at lower voltages of 10 V or less than plasma display panels or inorganic electroluminescent (EL) displays. It has the advantage of being able to drive, relatively low power consumption, and excellent color. In addition, organic electroluminescent devices are capable of displaying three colors of green, blue, and red, and thus are attracting much attention as next-generation rich color display devices.

In order for the organic electroluminescent device to sufficiently exhibit the above-described excellent characteristics, materials constituting the organic material layer in the device, such as a hole injecting material, a hole transporting material, a light emitting material, an electron transporting material, and an electron injecting material are supported by a stable and efficient material However, the development of a stable and efficient organic material layer material for an organic electroluminescence device has not been sufficiently developed yet. Therefore, there is a continuing need in the art for the development of new materials having low-voltage driving, high efficiency and long life.

The first problem to be solved by the present invention is to provide a novel aromatic compound having a low driving voltage, excellent light emission characteristics such as luminance, high thermal stability and long life as a light emitting layer material.

In addition, a second problem to be solved by the present invention is to provide an organic light emitting device having a low driving voltage and improved luminous efficiency using the aromatic compound.

In order to achieve the first object of the present invention,

It provides the aromatic compound represented by the following [Formula 1].

[Formula 1]

In the above formula (1)

R ₁ to R ₉ is a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, substituted or unsubstituted Heteroaryl group having 3 to 60 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 60 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, substituted or unsubstituted alkylamino group having 1 to 20 carbon atoms, substituted Or an unsubstituted arylamino group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, a substituted or unsubstituted carbon atom having 1 to 50 carbon atoms Arylalkylamino group, substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms, substituted or unsubstituted alkynyl group having 2 to 60 carbon atoms, hydroxyl group, nitro group, amino group, amidino group, hydrazine, Drazone, carboxyl group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid or salt thereof, substituted or unsubstituted aryloxy group having 5 to 60 carbon atoms, substituted or unsubstituted arylthio group, cyano group, halogen Group, deuterium and hydrogen, each independently the same or different,

X is C or N,

L is a chemical bond, substituted or unsubstituted alkylene having 1 to 60 carbon atoms, substituted or unsubstituted alkenylene having 2 to 60 carbon atoms, substituted or unsubstituted alkynylene having 2 to 60 carbon atoms, substituted or unsubstituted Heterocycloalkylene having 2 to 6 carbon atoms, including at least one selected from cycloalkylene having 3 to 60 carbon atoms, N, O and S, substituted or unsubstituted arylene having 6 to 50 carbon atoms and substituted or unsubstituted carbon number A divalent linking group selected from the group consisting of 3 to 50 heteroarylene,

M is an integer of 1 to 4, and when m is 2 or more, a plurality of Ls are the same or different.

In addition, the present invention to solve the second problem,

Anode; Cathode; Or it provides an organic electroluminescent device having a layer comprising an aromatic compound represented by the above [Formula 1] between the anode and the cathode.

According to an embodiment of the present invention, the aromatic compound may be included in the light emitting layer between the anode and the cathode.

According to another embodiment of the present invention, the organic light emitting device is one or more selected from the group consisting of a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer and an electron injection layer between the anode and the cathode It may further comprise a layer.

According to another embodiment of the present invention, the organic light emitting display device may be used in a display device, a display device, and a monochrome or white light emitting device.

As described above, since the aromatic compound represented by [Formula 1] according to the present invention has excellent light emitting ability as compared to the conventional material, the organic light emitting device including the same has a low driving voltage and excellent light emitting characteristics such as luminance. High thermal stability and long life can improve luminous efficiency.

1 is a cross-sectional view showing a laminated structure of an organic light emitting display device according to a preferred embodiment of the present invention.

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

The present invention is to improve the luminous efficiency, such as driving voltage, brightness and lifespan characteristics as compared to the conventional phosphorescent host material, characterized in that a variety of substituents are combined with a structure represented by the following [Formula 1].

[Formula 1]

In the above formula (1)

R ₁ to R ₉ is a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, substituted or unsubstituted Heteroaryl group having 3 to 60 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 60 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, substituted or unsubstituted alkylamino group having 1 to 20 carbon atoms, substituted Or an unsubstituted arylamino group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, a substituted or unsubstituted carbon atom having 1 to 50 carbon atoms Arylalkylamino group, substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms, substituted or unsubstituted alkynyl group having 2 to 60 carbon atoms, hydroxyl group, nitro group, amino group, amidino group, hydrazine, Drazone, carboxyl group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid or salt thereof, substituted or unsubstituted aryloxy group having 5 to 60 carbon atoms, substituted or unsubstituted arylthio group, cyano group, halogen Group, deuterium and hydrogen, each independently the same or different,

X is C or N,

L is a chemical bond, substituted or unsubstituted alkylene having 1 to 60 carbon atoms, substituted or unsubstituted alkenylene having 2 to 60 carbon atoms, substituted or unsubstituted alkynylene having 2 to 60 carbon atoms, substituted or unsubstituted Heterocycloalkylene having 2 to 6 carbon atoms, including at least one selected from cycloalkylene having 3 to 60 carbon atoms, N, O and S, substituted or unsubstituted arylene having 6 to 50 carbon atoms and substituted or unsubstituted carbon number A divalent linking group selected from the group consisting of 3 to 50 heteroarylene,

M is an integer of 1 to 4, and when m is 2 or more, a plurality of Ls are the same or different.

In addition, the "substituted" is substituted with one or more substituents, wherein R ₁ to R ₉ and L are each independently a hydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, Amino group, amidino group, hydrazine, hydrazone, carboxyl group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid or salt thereof, alkyl group of 1 to 60 carbon atoms, alkenyl group of 2 to 60 carbon atoms, alkynyl group of 2 to 60 carbon atoms, An alkoxy group having 1 to 60 carbon atoms, a cycloalkyl group having 3 to 60 carbon atoms, an aryl group having 6 to 60 carbon atoms, an aryloxy group having 6 to 60 carbon atoms, an arylthio group having 6 to 60 carbon atoms, a heteroaryl group having 2 to 60 carbon atoms It may be further substituted with a substituent containing a silicon carbide compound or a nitrogen carbide compound.

Specific examples of the aromatic compound according to the present invention may include any one compound selected from the group consisting of compounds represented by the following [Formula 2] to [Formula 224], but the present invention is not limited thereto.

[Formula 2] [Formula 3] [Formula 4] [Formula 5]

[Formula 6] [Formula 7] [Formula 8] [Formula 9]

[화학식 10] [화학식 11] [화학식 12] [화학식 13]

[Chemical Formula 11] [Chemical Formula 12] [Chemical 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 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]

 [Formula 97] [Formula 98] [Formula 99] [Formula 100]

 [Formula 101] [Formula 102] [Formula 103] [Formula 104]

 [Formula 105] [Formula 106] [Formula 107] [Formula 108]

 [Formula 109] [Formula 110] [Formula 111] [Formula 112]

 [Formula 113] [Formula 114] [Formula 115] [Formula 116]

 [Formula 117] [Formula 118] [Formula 119] [Formula 120]

 [Formula 121] [Formula 122] [Formula 123] [Formula 124]

 [Formula 125] [Formula 126] [Formula 127] [Formula 128]

 [Formula 129] [Formula 130] [Formula 131] [Formula 132]

 [Formula 133] [Formula 134] [Formula 135] [Formula 136]

 [Formula 137] [Formula 138] [Formula 139] [Formula 140]

 [Formula 141] [Formula 142] [Formula 143] [Formula 144]

   [Formula 145] [Formula 146] [Formula 147] [Formula 148]

 [Formula 149] [Formula 150] [Formula 151] [Formula 152]

 [Formula 153] [Formula 154] [Formula 155] [Formula 156]

 [Formula 157] [Formula 158] [Formula 159] [Formula 160]

  [Formula 161] [Formula 162] [Formula 163] [Formula 164]

 [Formula 165] [Formula 166] [Formula 167] [Formula 168]

 [Formula 169] [Formula 170] [Formula 171] [Formula 172]

 [Formula 173] [Formula 174] [Formula 175] [Formula 176]

 [Formula 177] [Formula 178] [Formula 179] [Formula 180]

 [Formula 181] [Formula 182] [Formula 183] [Formula 184]

 [Formula 185] [Formula 186] [Formula 187] [Formula 188]

 [Formula 189] [Formula 190] [Formula 191] [Formula 192]

 [Formula 193] [Formula 194] [Formula 195] [Formula 196]

   [Formula 197] [Formula 198] [Formula 199] [Formula 200]

   [Formula 201] [Formula 202] [Formula 203] [Formula 204]

    [Formula 205] [Formula 206] [Formula 207] [Formula 208]

    [Formula 209] [Formula 210] [Formula 211] [Formula 212]

   [Formula 213] [Formula 214] [Formula 215] [Formula 216]

   [Formula 217] [Formula 218] [Formula 219] [Formula 220]

   [Formula 221] [Formula 222] [Formula 223] [Formula 224]

In another aspect, the present invention provides an organic light emitting device having a layer comprising an aromatic compound represented by the above [Formula 1] between the anode and the cathode.

According to one embodiment of the present invention, the anode and the cathode further comprises one or more layers selected from the group consisting of a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer and an electron injection layer The compound of [Formula 1] may be included in the light emitting layer between the anode and the cathode, and the thickness of the light emitting layer is preferably 50 to 2,000 Pa.

In still another embodiment of the present invention, at least one or more of the hole injection layer, the hole transport layer, the hole blocking layer, the light emitting layer, the electron transport layer, the electron injection layer and the electron blocking layer is formed by a solution process. An organic electroluminescent device is provided.

The hole transport layer is laminated in order to easily inject holes from the anode, and as the material of the hole transport layer, electron donating molecules having a small ionization potential are used. Many amine derivatives are used.

The present invention is not particularly limited as long as it is commonly used in the art as a material of the hole transport layer. 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'-diphenyl benzidine (a-NPD) and the like can be used.

A hole injection layer (HIL) may be further stacked below the hole transport layer, and the hole injection layer material may also be used without particular limitation as long as it is commonly used in the art. For example, CuPc or Starburst type amines such as TCTA, m-MTDATA, etc., which are listed in the following chemical formulas, may be used.

The light emitting layer is a layer for emitting light by recombination of electrons or holes injected from the electron transport layer and the hole transport layer, and the light emitting portion may be in a layer of the light emitting layer or may be an interface between the light emitting layer and an adjacent layer.

According to an embodiment of the present invention, the light emitting layer may further include other host compounds and phosphorescent compounds in addition to the aromatic compound of [Formula 1]. In addition, the electron transport layer used in the organic electroluminescent device according to the present invention can transport electrons supplied from the cathode smoothly to the organic luminescent layer and inhibit the movement of holes which are not bonded in the organic luminescent layer, . The material for the electron transport layer is not particularly limited as long as it is commonly used in the art. For example, oxadiazole derivative PBD, BMD, BND or Alq ₃ can be used.

Meanwhile, an electron injection layer (EIL) may be further stacked on the upper portion of the electron transport layer to facilitate electron injection from the cathode and ultimately improve power efficiency. The electron injection layer material may also be stacked. If it is conventionally used in the art can be used without particular limitation, for example, materials such as LiF, NaCl, CsF, Li ₂ O, BaO and the like can be used.

The organic electroluminescent device according to one embodiment of the present invention can be used for a display device, a display device, a monochrome or white illumination device, and the like.

1 is a cross-sectional view showing the structure of an organic light emitting display device according to the present invention. The organic light emitting diode 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, the hole injection layer 30 and the electron The injection layer 70 may be further included. In addition, an intermediate layer of one or two layers may be further formed, and a hole blocking layer or an electron blocking layer may be further formed.

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

The hole injection layer 30 is vacuum-evaporated or spin-coated on the anode 20 electrode to form the hole injection layer 30. 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, the organic light emitting layer 50 is laminated on the hole transport layer 40, and a hole blocking layer (not shown) is selectively formed on the organic light emitting layer 50 to form a thin film as a vacuum deposition method or a spin coating method. can do. When the holes pass through the organic light emitting layer and enter the cathode, the lifetime and efficiency of the hole blocking layer are reduced. Therefore, the hole blocking layer plays a role of preventing such a problem by using a material having a very low HOMO level. The hole blocking material used herein is not particularly limited, but it is required to have an ionization potential higher than that of a light emitting compound while having an electron transporting ability. Typically, BAlq, BCP, TPBI and the like can be used.

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

Hereinafter, the present invention will be described in more detail with reference to the following examples, which are merely illustrative to assist in understanding the present invention, but the scope of the present invention is not limited thereto.

Synthesis Example 1 Synthesis of Chemical Formula 2

Synthesis Example 1-1. Synthesis of <1-a>

<1-a> was synthesized according to Reaction Scheme 1 below.

[Reaction Scheme 1]

<1-a>

In a 2000 mL round bottom flask, 100 g (0.598 mol) of carbazole was added to 250 mL of N, N-diethylformamide under nitrogen, and the reaction mixture was cooled to 0 ° C. 106.44 g (0.598 mol) of n-bromosuccinimide was dissolved in 530 mL of n, ene-dimethylamide and added dropwise. After the dropwise addition, the mixture was stirred at room temperature. When the reaction was completed, the resultant of the reaction was poured into water, stirred, filtered, washed with water and methanol to give 76.4 g (51.9%) of <1-a>.

Synthetic example  1-2. Synthesis of <1-b>

<1-b> was synthesized by the following Scheme 2.

[Reaction Scheme 2]

<1-b>

76.4 g (0.31 mol) of compound represented by formula <1-a> obtained from Scheme 1 under nitrogen in a 2000 mL round bottom flask, 111.8 g (0.466 mol) of iodobenzene, 86 g (0.62 mol) of potassium carbonate, chloride 4.32 g (0.02 mol) of copper and 650 mL of dimethylsulfoxide were added and then refluxed for 12 hours. When the reaction was terminated, the resultant of the reaction was separated into layers to remove the aqueous layer, and the organic layer was separated and concentrated under reduced pressure to give <1-b> 76 g (yield 76%) through column chromatography.

Synthetic example  1-3. Synthesis of <1-c>

&Lt; 1-c > was synthesized by the following Reaction Scheme 3.

Scheme 3

<1-c>

In a 1000 mL round bottom flask, 76 g (0.236 mol) of a compound represented by Chemical Formula <1-b> obtained from Scheme 2 and 600 mL of tetrahydrofuran were added thereto, and the reaction temperature was cooled to minus 78 ° C. After cooling, 221.14 mL (0.354 mol) of n-butyllithium (1.6M hexane solution) is slowly added dropwise. After stirring for 1 hour while maintaining a low temperature, 25.9 g (0.354 mol) of N, N-dimethylformamide was added dropwise, followed by stirring at room temperature for 12 hours. After completion of the reaction, 200 mL of 2 N HCl solution was added dropwise, followed by extraction with ethyl acetate and water. The organic layer is anhydrous and then depressurized to remove the organic solvent. After concentration under reduced pressure, the residue was separated by column chromatography using hexane to obtain 52.3g (yield 81.7%) of <1-c>.

Synthetic example  1-4. Synthesis of <1-d>

<1-d> was synthesized according to Scheme 4 below.

[Reaction Scheme 4]

<1-d>

In a 2000 mL round bottom flask, 52.3 g (0.194 mol) of the compound represented by the formula <1-c> obtained from Scheme 3 and 37 g (0.176 mol) of 9,10-phenanthrendione were dissolved in 1200 mL of acetic acid and 30 g of ammonium acetate under nitrogen. And reflux for 16 hours. After the reaction was completed, the reaction product was cooled to room temperature, and the product was filtered and washed with water and sodium hydrogen carbonate solution to obtain 70.6 g (yield 86.9%) of <1-d>.

Synthetic example  1-5. Synthesis of [Formula 2]

[Scheme 2] was synthesized according to Scheme 5 below.

[Reaction Scheme 5]

(2)

17.1 g (0.037 mol) of compound represented by formula <1-d> obtained from Scheme 4, 6.0 g (0.019 mol) of 4-bromotriphenylamine, tris (dibenzideneacetone) dipalladium in a 1 L round bottom flask (0) 0.17 g (0.19 mmol), 18-crown-6-ether 0.15 g (0.56 mmol), 0.5 g (0.001 mol) tributylbutylphosphine, 5.1 g (0.04 mol) potassium carbonate and 400 mL zylene And refluxed for 12 hours. After completion of the reaction was extracted and the organic layer was concentrated under reduced pressure and recrystallized with hexane to give 5.6g (42.9%).

MS (MALDI-TOF): m / z 704.27 [M] ⁺

Anal. Calc. for C ₄₉ H ₃₂ N ₆ :

C, 83.50; H, 4.58; N, 11.92;

Found C, 83.48; H, 4.59; N, 11.93

Synthetic example  2. Synthesis of Chemical Formula 7

Synthetic example  2-1. Synthesis of <2-a>

<2-a> was synthesized by the following Reaction Scheme 6.

[Reaction Scheme 6]

<2-a>

Except for using dibenzothiophene instead of <1-c> used in Scheme 6 it was synthesized in the same manner to give 57.6 g (yield 86.4%) of <2-a>.

Synthetic example  2-2. Synthesis of <2-b>

<2-b> was synthesized by the following Scheme 7.

[Reaction Scheme 7]

<2-b>

Except for using <2-a> synthesized in Scheme 6 instead of <1-c> used in Scheme 4, it was synthesized in the same manner to obtain 15.3 g (yield 71.5%) of <2-b>.

Synthetic example  2-3. Synthesis of Formula 7

[Scheme 7] was synthesized according to Scheme 8 below.

[Reaction Scheme 8]

[Formula 7]

Except for using <2-b> synthesized in Scheme 7 instead of <1-d> used in Scheme 5 it was synthesized in the same manner to obtain 6.4 g (yield 47.3%).

MS (MALDI-TOF): m / z 645.20 [M] ⁺

Anal. Calc. for C ₄₃ H ₂₇ N ₅ S:

C, 79.98; H, 4.21; N, 10.84; S, 4.97;

Found C, 79.99; H, 4.22; N, 10.83; S, 4.96

Synthetic example  3. Synthesis of Compound (25)

Synthetic example  3-1. Synthesis of <3-a>

<3-a> was synthesized by the following Reaction Scheme 9.

[Reaction Scheme 9]

<3-a>

Synthesis was carried out in the same manner except for using 2-bromoquinoline instead of <1-c> used in Scheme 6 to give 40.1 g (yield 74.3%) of <3-a>.

Synthetic example  3-2. Synthesis of <3-b>.

&Lt; 3-b > was synthesized according to Reaction Scheme 10 below.

[Reaction Scheme 10]

<3-b>

Except for using <3-a> synthesized in Scheme 9 instead of <1-c> used in Scheme 4, it was synthesized in the same manner to obtain 18.1 g (yield 67.8%) of <3-b>.

Synthetic example  3-3. Synthesis of Formula 25.

[Scheme 25] was synthesized according to Scheme 11 below.

[Reaction Scheme 11]

(25)

Except for using <3-b> synthesized in Scheme 10 instead of <1-d> used in Scheme 5 it was synthesized in the same manner to obtain 5.7 g (yield 45.2%).

MS (MALDI-TOF): m / z 590.22 [M] ⁺

Anal. Calc. for C ₄₀ H ₂₆ N ₆ :

C, 81.34; H, 4.44; N, 14.23;

Found C, 81.32; H, 4. 45; N, 14.24

Synthetic example  4. Synthesis of Chemical Formula 29

Synthetic example  4-1. Synthesis of <4-a>.

&Lt; 4-a > was synthesized by the following Reaction Scheme 12.

[Reaction Scheme 12]

<4-a>

440 g (2.178 mol) with 1-bromo-2-nitrobenzene, 304.2 g (2.396 mol) phenylboronic acid-di5, tetrakistriphenylphosphinepalladium (Pd (PPh ₃ )) in a 1000 mL round bottom flask ₄ ) 50.5 g (0.044 mol), potassium carbonate 602.1 g (4.356 mol), 1800 mL toluene. 1800 mL of tetrahydrofuran and 800 mL of water were added and refluxed for 12 hours. After the reaction is completed, the reaction solution is cooled to room temperature, extracted with ethyl acetate and water, the organic layer is anhydrous and the organic layer is concentrated under reduced pressure. After concentration under reduced pressure, 410 g (92.2%) of <4-a> were obtained by using column chromatography.

Synthetic example  4-2. Synthesis of <4-b>

<4-b> was synthesized by the following Reaction Scheme 13.

[Reaction Scheme 13]

<4-b>

410 g (2.007 mol) of <4-a> synthesized in Scheme 12, 1579.7 g (6.022 mol) of triphenylphosphine and 4000 mL of dichlorobenzene were added and refluxed for 12 hours. After the reaction is completed, the reaction solution is cooled to room temperature, extracted with ethyl acetate and water, the organic layer is anhydrous and the organic layer is concentrated under reduced pressure. After concentration under reduced pressure, 3004-g (55.7%) of <4-b> was obtained using column chromatography.

Synthetic example  4-3. Synthesis of <4-c>

<4-c> was synthesized by the following Scheme 14.

[Reaction Scheme 14]

<4-c>

Except for using <4-b> synthesized in Scheme 13 instead of the carbazole used in Scheme 1, the synthesis was carried out in the same manner to obtain 100 g (yield 68.6%).

Synthetic example  4-4. Synthesis of <4-d>

<4-d> was synthesized according to Scheme 15 below.

[Reaction Scheme 15]

<4-d>

Except for using <4-c> synthesized in Scheme 14 instead of <1-a> used in Scheme 2, it was synthesized in the same manner to obtain 97.6 g (yield 71.6%) of <4-d>.

Synthetic example  4-5. Synthesis of <4-e>.

<4-e> was synthesized according to Scheme 16 below.

[Reaction Scheme 16]

<4-e>

Except for using <4-d> synthesized in Scheme 15 instead of 1-c used in Scheme 6 to give 34.6 g (yield 87.6%) of <4-e>.

Synthetic example  4-6. Synthesis of <4-f>

<4-f> was synthesized by the following Scheme 17.

[Reaction Scheme 17]

<4-f>

Except for using <4-e> synthesized in Scheme 9 instead of 1-c used in Scheme 4 it was synthesized in the same manner to give 18.1 g (yield 67.8%).

Synthetic example  4-7. Synthesis of Chemical Formula 29

[Scheme 29] was synthesized according to Scheme 18 below.

[Reaction Scheme 18]

[Chemical Formula 29]

Except for using <4-f> synthesized in Scheme 17 instead of <1-d> used in Scheme 5 it was synthesized in the same manner to obtain 4.6 g (yield 36.7%).

MS (MALDI-TOF): m / z 708.29 [M] ⁺

Anal. Calc. for C ₄₉ H ₂₈ D ₄ N _{6 :}

C, 83.03; H, 5.12; N, 1.86;

Found C, 83.02; H, 4.13; N, 5.12

Synthetic example  5. Synthesis of Chemical Formula 40

Synthetic example  5-1. Synthesis of <5-a>

&Lt; 5-a > was synthesized according to the following Reaction Scheme 19.

Scheme 19

<5-a>

Add 200 g (0.73 mol) of 2-bromo-9,9'-dimethylfluorene and 2400 mL of tetrahydrofuran to a 5 L round bottom flask, stir for 30 minutes under nitrogen, and cool the reaction to -78 ° C. Let's do it. 549 mL (0.88 mol) of 1.6 N butyllithium was slowly added dropwise. After stirring for 24 hours at room temperature the temperature of the reaction is cooled to -78 ° C. Slowly add 223 g (0.88 mol) of iodine. The temperature was raised to room temperature and stirred for 12 hours. After completion of the reaction, the reaction was terminated with an aqueous solution of sodium thiosulfate, and extracted. The organic layer was concentrated under reduced pressure, and then separated by column chromatography using hexane, thereby obtaining 209 g (yield 89%).

Synthetic example  5-2. Synthesis of <5-b>.

<5-b> was synthesized according to Scheme 20 below.

[Reaction Scheme 20]

<5-b>

<5-a> 558.4 g (1.74 mol) synthesized in Scheme 19 in a 2 L round bottom flask, 100 g (0.58 mol) of 4-bromoaniline, 11.1 g (0.058 mol) of copper iodide (CuI), tree 370.2 g (1.74 mol) of potassium phosphate (K ₃ PO ₄ ), 19.9 g (0.17 mol) of trans-1,2-cyclohexanediamine, and 1000.0 mL of 1,4-dioxane were added and refluxed for 12 hours. After the reaction was completed, the mixture was cooled to room temperature, extracted with 1 L of water, and the organic layer was anhydrous and concentrated under reduced pressure. Then, 200 g (yield 61.8%) of <5-b> was obtained by using an adsorption column chromatography.

Synthetic example  5-3. Synthesis of <5-c>

<5-c> was synthesized according to Scheme 21 below.

[Reaction Scheme 21]

<5-c>

Except for using 2-bromobenzothiazole instead of <1-c> used in Scheme 6 it was synthesized in the same manner to give 35.6 g (yield 81.4%) of <5-c>.

Synthetic example  5-4. Synthesis of <5-d>.

<5-d> was synthesized according to Scheme 22 below.

[Reaction Scheme 22]

<5-d>

Except for using <5-c> synthesized in Scheme 21 instead of <1-c> used in Scheme 4, it was synthesized in the same manner to obtain 16.9 g (yield 74.6%) of <5-d>.

Synthetic example  5-5. Synthesis of <5-e>.

[Scheme 40] was synthesized according to Scheme 23 below.

[Reaction Scheme 23]

[Formula 40]

In the same manner except that <5-d> synthesized in Scheme 22 was used instead of <1-d> used in Scheme 5 and <5-b> synthesized in Scheme 20 instead of 4-bromotriphenylene Synthesis | combination obtained 5.3 g (42.5% of yield).

MS (MALDI-TOF): m / z 828.30 [M] ⁺

Anal. Calc. for C ₅₆ H ₄₀ N ₆ S:

C, 81.13; H, 4.86; N, 10.14; S, 3.87;

Found C, 81.11; H, 4.87; N, 10.15; S, 3.87

Synthetic example  6. Synthesis of Chemical Formula 56

Synthetic example  6-1. Synthesis of <6-a>

<6-a> was synthesized according to Scheme 24 below.

[Reaction Scheme 24]

<6-a>

Except for using 6-bromo-2-methylquinoline instead of <1-c> used in Scheme 6 it was synthesized in the same manner to give 47.9 g (yield 83.8%) of <6-a>.

Synthetic example  6-2. Synthesis of <6-b>

<6-b> was synthesized according to Scheme 25 below.

[Reaction Scheme 25]

<6-d>

Except for using <6-a> synthesized in Scheme 24 instead of <1-c> used in Scheme 4, it was synthesized in the same manner to obtain 14.3-g (yield 79.3%) of <6-b>.

Synthetic example  6-3. Synthesis of Chemical Formula 56

To [scheme 56] was synthesized by the following Reaction Scheme 26.

[Reaction Scheme 26]

(56)

Instead of <1-c> used in Scheme 4, <6-b> synthesized in Scheme 25 was used, and 4-bromo-4 ', 4' '-dimethyltriphenylamine was used instead of 4-bromotriphenylene. Except that synthesized in the same manner to obtain 7.1 g (yield 43.6%).

MS (MALDI-TOF): m / z 632.27 [M] ⁺

Anal. Calc. for C ₄₃ H ₃₂ N ₆ :

C, 81.62; H, 5.10; N, 13.28;

Found C, 81.60; H, 5.09; N, 13.27

Synthetic example  7. Synthesis of Chemical Formula 64

Synthetic example  7-1. Synthesis of <7-a>

<7-a> was synthesized according to Scheme 27 below.

[Reaction Scheme 27]

<7-a>

200 g (0.895 mol) of 4-bromophenylhydrazinehydrochloride, 97 g (1.345 mol) of 2-butanone, and 1000 mL of ethanol were added to a 2000 mL round bottom flask, and the mixture was refluxed for 24 hours. After completion of the reaction, the mixture was extracted and the organic layer was concentrated under reduced pressure, and the crystals were filtered to give 135 g (67.3%) of <7-a>.

Synthetic example  7-2. Synthesis of <7-b>.

<7-b> was synthesized according to Scheme 28 below.

[Reaction Scheme 28]

<7-b>

Except for using <7-a> synthesized in Scheme 27 instead of <1-a> used in Scheme 2 to give 160 g (yield 64.6%) of <7-d>.

Synthetic example  7-3. Synthesis of <7-c>.

<7-c> was synthesized according to Scheme 29 below.

[Reaction Scheme 29]

<7-c>

<7-c> 57.4 g (yield 79.3%) was obtained by synthesizing in the same manner except for using <7-b> synthesized in Scheme 28 instead of <1-c> used in Scheme 6.

Synthetic example  7-4. Synthesis of <7-d>

<7-d> was synthesized according to Scheme 30 below.

[Reaction Scheme 30]

<7-d>

Except for using <7-c> synthesized in Scheme 29 instead of <1-c> used in Scheme 4, it was synthesized in the same manner to obtain 17.4 g (yield 86.1) of <6-d>.

Synthetic example  7-5. Synthesis of <7-e>

<7-e> was synthesized according to Scheme 31 below.

[Reaction Scheme 31]

<7-e>

Except for using 4-iodobiphenyl instead of <5-a> used in Scheme 20 it was synthesized in the same manner to give 38.4 g (yield 74.6%) of <7-e>.

Synthetic example  7-6. Synthesis of <7-f>

&Lt; 7-f > was synthesized by the following Reaction Formula 32.

[Reaction Scheme 32]

<7-f>

Except for using iodobenzene instead of <5-a> in Scheme 20 it was synthesized in the same manner to give 34.3 g (yield 71.8%) of <7-f>.

Synthetic example  7-7. Synthesis of Formula 64

[Scheme 64] was synthesized according to Scheme 33 below.

[Reaction Scheme 33]

&Lt; EMI ID =

In the same manner except that <7-d> synthesized in Scheme 30 was used instead of <1-c> used in Scheme 4 and <7-f> synthesized in Scheme 32 instead of 4-bromotriphenylene It synthesize | combined and obtained 4.8 g (yield 35.7%).

MS (MALDI-TOF): m / z 758.32 [M] ⁺

Anal. Calc. for C ₅₃ H ₃₈ N _{6 :}

C, 83.88; H, 5.05; N, 11.07;

Found C, 83.87; H, 5.04; N, 11.09

Synthetic example  8. Synthesis of Chemical Formula 138

Synthetic example  8-1. Synthesis of <8-a>

<8-a> was synthesized according to Scheme 34 below.

[Reaction Scheme 34]

<8-a>

91.0 g (0.529 mol) of 4-bromoaniline, 514.2 mL of water, and 1028.3 mL of 12 N hydrochloric acid were added to a 5 L round bottom flask, and the internal temperature was reduced to 0 ° C. under a nitrogen atmosphere. After lowering to 0 ° C, 36.5 g (0.529 mol) of sodium nitrile (NaNO ₂ ) is dissolved in 365.1 mL of water, and then slowly added dropwise to the reaction solution. After stirring for 30 minutes, 501.6 g of tin chloride (SnCl ₂ ) is dissolved in 350 mL of 12 N hydrochloric acid and slowly added dropwise. When the dropwise addition was completed, the reaction solution was heated to room temperature, stirred for 3 hours, cooled to 5 ° C. after 3 hours, and filtered to obtain 116.2 g (yield 98.3%) of <8-a>.

Synthetic example  8-2. Synthesis of <8-b>

<8-b> was synthesized by the following Scheme 35.

[Reaction Scheme 35]

<8-b>

116.2 g (0.520 mol) of <8-a> synthesized in Scheme 34, 51.0 g (0.520 mol) of cyclohexanone, and 1162.0 mL of ethanol were added to a 2 L round bottom flask and refluxed for 10 hours. After the reaction was completed, the reaction solution was concentrated and then column chromatography was used to obtain 128.6 g (yield 98.9%) of <8-b>.

Synthetic example  8-3. Synthesis of <8-c>

<8-c> was synthesized according to Scheme 36 below.

[Reaction Scheme 36]

<8-c>

In a 1 L round bottom flask, 60.0 g (0.240 mol) of <5-d> synthesized in Scheme 23, 73.4 g (0.360 mol) of iobenzene, 2.3 g (0.012 mol) of copper iodide (CuI), tripotassium phosphate ( K ₃ PO ₄ ) 106.96 g (0.504 mol), 54.8 g (0.480 mol) of trans-1,2-cyclohexanediamine and 300.0 mL of 1,4-dioxane were added and refluxed for 12 hours. After the reaction was completed, the mixture was cooled to room temperature, extracted with 1 L of water, and the organic layer was anhydrous and concentrated under reduced pressure. Then, 72.0 g (yield 92.0%) of <8-c> was obtained by using an adsorption column chromatography.

Synthetic example  8-4. Synthesis of <8-d>

<8-d> was synthesized according to Scheme 37 below.

[Reaction Scheme 37]

<8-d>

Except for using <8-c> synthesized in Scheme 26 instead of <1-c> used in Scheme 6 it was synthesized in the same manner to obtain 39.1 g (yield 83.5%) of <8-d>.

Synthetic example  8-5. Synthesis of <8-e>

<8-e> was synthesized according to Scheme 38 below.

[Reaction Scheme 38]

<8-e>

Except for using <8-d> synthesized in Scheme 37 instead of <1-c> used in Scheme 4, it was synthesized in the same manner to obtain 15.3 g (yield 74.1%) of <8-e>.

Synthetic example  8-6. Synthesis of <8-f>.

<8-f> was synthesized by the following Scheme 39.

[Reaction Scheme 39]

<8-f>

Except for using 1-iodo-4-bromobenzene instead of <5-a> used in Scheme 20 to give 51.6 g (yield 78.2%) of <8-f>.

Synthetic example  8-7. Synthesis of Chemical Formula 138

By following Reaction Scheme 40, [Formula 138] was synthesized.

[Reaction Scheme 40]

&Lt; EMI ID =

In the same manner except for using <8-e> synthesized in Scheme 38 instead of <1-c> used in Scheme 4 and <8-f> synthesized in Scheme 39 instead of 4-bromotriphenylene. It synthesize | combined and obtained 6.2g (yield 39.6%).

MS (MALDI-TOF): m / z 706.28 [M] ⁺

Anal. Calc. for C ₄₉ H ₃₄ N ₆ :

C, 83.26; H, 4. 85; N, 11.89;

Found C, 83.23; H, 4.87; N, 11.90

Synthetic example  9. Synthesis of Chemical Formula 165

Synthetic example  9-1. Synthesis of <9-a>

<9-a> was synthesized by the following Scheme 41.

[Reaction Scheme 41]

<9-a>

209 g (0.63 mol) of compound represented by the formula 5-a and 122.1 g (0.789 mol) of 2-bromoaniline, tris (dibenzideneacetone) dipalladium (0) 12 in a 5 L round bottom flask g (0.013 mol), 14.5 g (0.026 mol) of 1,1'bis (diphenylphosphino) ferrocene, 94.1 g (0.979 mol) of sodium tert-butoxide, and 2100 mL of toluene were added and refluxed for 12 hours. After completion of the reaction, the mixture was filtered and concentrated under reduced pressure, and then separated by column chromatography using hexane to obtain 164 g (yield 69%) of <9-a>.

Synthetic example  9-2. Synthesis of <9-b>

<9-b> was synthesized according to Scheme 42 below.

[Reaction Scheme 42]

<9-b>

In a 2 L round bottom flask, 70 g (0.19 mol) of the compound represented by the formula <9-a> obtained from Scheme 41, 1.4 g (0.004 mol) of tricyclohexylphosphinium tetrafluoroborate, and 0.431 g (0.002 mol) of palladium acetate ), 53.1 g (0.384 mol) of potassium carbonate and 700 mL of N, N-dimethylacetamide were added and refluxed for 12 hours. After the completion of the reaction, the mixture was extracted and the organic layer was concentrated under reduced pressure, recrystallized with hexane and dried to obtain 46.3 g (85%) of <9-b>.

Synthetic example  9-3. Synthesis of <9-c>

<9-c> was synthesized by the following Scheme 43.

[Reaction Scheme 43]

<9-c>

<9-b> synthesized in Scheme 42 instead of <1-a> used in Scheme 2 was synthesized in the same manner, except that 1-iodo-4-bromobenzene was used instead of iodobenzene. -c> 29.5 g (68.3% yield) were obtained.

Synthetic example  9-4. Synthesis of <9-d>

<9-d> was synthesized according to Scheme 44 below.

[Reaction Scheme 44]

<9-d>

Synthesis was carried out in the same manner except that 4-bromoanisoquinoline was used instead of <1-c> used in Scheme 6 to give 26.5 g (yield 79.8%) of <9-d>.

Synthetic example  9-5. Synthesis of <9-e>

<9-e> was synthesized by the following Scheme 45.

[Reaction Scheme 45]

<9-e>

Except for using <9-d> synthesized in Scheme 44 instead of <1-c> used in Scheme 4 to give 17.4 g (yield 64.5%) of <9-e>.

Synthetic example  9-6. Synthesis of Formula 165

To [Scheme 165] was synthesized by the following Reaction Scheme 46.

[Reaction Scheme 46]

Formula 165

In the same manner except that <9-e> synthesized in Scheme 45 was used instead of <1-c> used in Scheme 4 and <9-c> synthesized in Scheme 43 instead of 4-bromotriphenylene. It synthesize | combined and obtained 7.4 g (yield 41.3%).

MS (MALDI-TOF): m / z 704.27 [M] ⁺

Anal. Calc. for C ₄₉ H ₃₂ N ₆ :

C, 83.50; H, 4.58; N, 11.92;

Found C, 83.48; H, 4.59; N, 11.93

Synthetic example  10. Synthesis of Chemical Formula 196

Synthetic example  10-1. Synthesis of <10-a>

<10-a> was synthesized by the following reaction scheme 47.

[Reaction Scheme 47]

<10-a>

87 g (0.576 mol) of methyl anthranilate, 135.1 g (0.478 mol) of 1-bromo-4-iodobenzene, 1.3 g (0.006) of palladium acetate (Pd (OAc) ₂ ) under nitrogen in a 5000 mL round bottom flask mol), 10 g (0.017 mol) of xantose, 217.5 g (0.668 mol) of cesium carbonate and 2500 mL of toluene were added and refluxed for 6 hours. When the reaction was terminated, the resultant of the reaction was separated into layers to remove the aqueous layer, and the organic layer was separated and concentrated under reduced pressure to obtain 110 g (75%) through column chromatography.

Synthetic example  10-2. Synthesis of <10-b>

&Lt; 10-b > was synthesized by the following Reaction Formula 48.

[Reaction Scheme 48]

<10-b>

27 g (0.088 mol) of Compound 1-a obtained from Scheme 1 and 400 mL of diisopropyl ether were added to a 1000 mL round bottom flask under nitrogen, and 309 mL of methylmagnesium bromide was slowly added dropwise thereto. After the dropwise addition, the mixture was stirred at 50 ° C. When the reaction was terminated, the resultant of the reaction was separated into layers to remove the aqueous layer, and the organic layer was separated and concentrated under reduced pressure to obtain 40 g (98%) through column chromatography.

Synthetic example  10-3. Synthesis of <10-c>

<10-c> was synthesized by the following Scheme 49.

[Reaction Scheme 49]

<10-c>

40 g (0.087 mol) of the compound represented by Chemical Formula 10-b obtained from Scheme 48 and 550 mL of phosphoric acid were added to a 1000 mL round bottom flask, followed by stirring at 60 ° C. When the reaction was completed, water was added to the resultant of the reaction and stirred. After stirring, the mixture was filtered and washed with water and methanol. Column chromatography gave 37 g (94%) of <10-c>.

Synthetic example  10-4. Synthesis of <10-d>

<10-d> was synthesized by the following Scheme 50.

[Reaction Scheme 50]

<10-d>

Except for using <10-c> synthesized in Scheme 42 instead of <1-a> used in Scheme 2 it was synthesized in the same manner to obtain 39.4 g (yield 73.5%) of <10-d>.

Synthetic example  10-5. Synthesis of <10-e>

<10-e> was synthesized according to Scheme 51 below.

[Reaction Scheme 51]

<10-e>

Except for using <10-d> synthesized in Scheme 50 instead of <1-c> used in Scheme 6 it was synthesized in the same manner to obtain 15.3 g (yield 68.1%) of <10-e>.

Synthetic example  10-6. Synthesis of <10-f>

<10-f> was synthesized by the following Scheme 52.

[Reaction Scheme 52]

<10-f>

Except for using <10-e> synthesized in Scheme 51 instead of <1-c> used in Scheme 4 it was synthesized in the same manner to obtain 13.6 g (yield 67.4%).

Synthetic example  10-7. Synthesis of <10-g>

<10-g> was synthesized according to Scheme 53 below.

[Reaction Scheme 53]

<10-g>

Except for using 2-iodonaphthalene instead of <5-a> used in Scheme 20, the synthesis was carried out in the same manner to obtain 29.4 g (yield 72.4%) of <10-g>.

Synthetic example  10-8. Synthesis of <10-h>.

<10-h> was synthesized according to Scheme 54 below.

[Reaction Scheme 54]

<10-h>

Except for using iodobenzene instead of <5-a> in Scheme 20 it was synthesized in the same manner to give 24.8 g (yield 67.3%) of <10-h>.

Synthetic example  10-9. Synthesis of Chemical Formula 196

By following Scheme 55, [Formula 196] was synthesized.

[Reaction Scheme 55]

[196]

The same method as used in <10-f> synthesized in Scheme 54 instead of <1-c> used in Scheme 4 and <10-h> synthesized in Scheme 54 instead of 4-bromotriphenylamine It synthesize | combined and obtained 5.6 g (yield 39.4%).

MS (MALDI-TOF): m / z 796.33 [M] ⁺

Anal. Calc. for C ₅₆ H ₄₀ N ₆ :

C, 84.40; H, 5.06; N, 10.55;

Found C, 84.41; H, 5.07; N, 10.57

Example

Fabrication of Organic Light Emitting Diode

The ITO glass was patterned to have a light emitting area of 2 mm x 2 mm and then cleaned. After mounting the substrate in a vacuum chamber, the base pressure is 1x10 ^-6 torr and the organic material is placed on the ITO DNTPD (700 kPa), NPD (300 kPa), the compound + Ir (ppy) ₃ (prepared by the present invention) 10%) (300 Å), Alq ₃ (350 mmW), LiF (5 mmW), and Al (1,000 mmW) were formed in this order and measured at 0.4 mA.

Comparative Example

The organic light emitting diode device for the comparative example was manufactured in the same manner except for using CBP, which is generally used as a phosphorescent host material, instead of the compound prepared by the invention in the device structure of the above embodiment.

division Host Dopant Doping concentration% V CD / m ² CIEx CIEy T ₈₀ ( Hr ) Comparative Example 1 CBP Ir (ppy) ₃ 10 7.93 3801 0.297 0.624 68 Example 1 2 Ir (ppy) ₃ 10 4.02 5189 0.279 0.625 170 Example 2 7 Ir (ppy) ₃ 10 3.99 5094 0.293 0.625 120 Example 3 25 Ir (ppy) ₃ 10 4.12 5293 0.299 0.623 157 Example 4 29 Ir (ppy) ₃ 10 3.96 4889 0.297 0.624 107 Example 5 40 Ir (ppy) ₃ 10 4.08 4938 0.289 0.623 121 Example 6 56 Ir (ppy) ₃ 10 4.11 5097 0.299 0.625 132 Example 7 64 Ir (ppy) ₃ 10 3.92 4968 0.301 0.629 117 Example 8 79 Ir (ppy) ₃ 10 4.24 5496 0.289 0.625 109 Example 9 94 Ir (ppy) ₃ 10 4.08 5678 0.276 0.624 186 Example 10 109 Ir (ppy) ₃ 10 4.13 5093 0.279 0.629 201 Example 11 117 Ir (ppy) ₃ 10 3.99 4987 0.286 0.623 186 Example 12 123 Ir (ppy) ₃ 10 4.06 5064 0.294 0.625 106 Example 13 138 Ir (ppy) ₃ 10 3.87 4783 0.293 0.624 110 Example 14 151 Ir (ppy) ₃ 10 4.18 5196 0.301 0.629 106 Example 15 165 Ir (ppy) ₃ 10 4.06 5369 0.298 0.623 197 Example 16 168 Ir (ppy) ₃ 10 4.13 5084 0.302 0.632 143 Example 17 182 Ir (ppy) ₃ 10 4.24 5263 0.291 0.629 132 Example 18 196 Ir (ppy) ₃ 10 4.15 5489 0.296 0.625 126 Example 19 201 Ir (ppy) ₃ 10 3.93 4953 0.289 0.622 189 Example 20 215 Ir (ppy) ₃ 10 4.07 5064 0.294 0.623 164

As shown in Table 1, the aromatic compound according to the present invention has a low driving voltage and excellent luminous efficiency as compared to CBP which is used as a phosphorescent host material.

10: substrate 20: anode
30: hole injection layer 40: hole transport layer
50: organic light emitting layer 60: electron transporting layer
70: electron injection layer 80: cathode

Claims (6)

An aromatic compound represented by the following [Formula 1]:
[Chemical Formula 1]

In [Formula 1],
R ₁ to R ₉ is a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, substituted or unsubstituted Heteroaryl group having 3 to 60 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 60 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, substituted or unsubstituted alkylamino group having 1 to 20 carbon atoms, substituted Or an unsubstituted arylamino group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, a substituted or unsubstituted carbon atom having 1 to 50 carbon atoms Arylalkylamino group, substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms, substituted or unsubstituted alkynyl group having 2 to 60 carbon atoms, hydroxyl group, nitro group, amino group, amidino group, hydrazine, Drazone, carboxyl group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid or salt thereof, substituted or unsubstituted aryloxy group having 5 to 60 carbon atoms, substituted or unsubstituted arylthio group, cyano group, halogen Group, deuterium and hydrogen, each independently the same or different,
X is C or N,
L is a chemical bond, substituted or unsubstituted alkylene having 1 to 60 carbon atoms, substituted or unsubstituted alkenylene having 2 to 60 carbon atoms, substituted or unsubstituted alkynylene having 2 to 60 carbon atoms, substituted or unsubstituted Heterocycloalkylene having 2 to 6 carbon atoms, including at least one selected from cycloalkylene having 3 to 60 carbon atoms, N, O and S, substituted or unsubstituted arylene having 6 to 50 carbon atoms and substituted or unsubstituted carbon number A divalent linking group selected from the group consisting of 3 to 50 heteroarylene,
M is an integer of 1 to 4, and when m is 2 or more, a plurality of Ls are the same or different. The method of claim 1,
An aromatic compound, characterized in that any one selected from the group of compounds represented by the formula [2] to [Formula 224]:

[Chemical Formula 2] &lt; EMI ID =

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

[Chemical Formula 11] [Chemical Formula 12] [Chemical Formula 13]

[Chemical Formula 14] [Chemical Formula 15]

[Chemical Formula 20] [Chemical Formula 20]

[Chemical Formula 22] [Chemical Formula 23] [Chemical Formula 25]

[Chemical Formula 28] [Chemical Formula 28]

[Chemical Formula 32] [Chemical Formula 32]

[Chemical Formula 35] [Chemical Formula 35]

[Chemical Formula 40] [Chemical Formula 40] [Chemical Formula 40]

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

[Chemical Formula 48] [Chemical Formula 48] [Chemical Formula 48]

[Chemical Formula 51] [Chemical Formula 52] [Chemical Formula 53]

[Chemical Formula 55] [Chemical Formula 55] [Chemical Formula 55]

[Chemical Formula 60] [Chemical Formula 61]

[Formula 62] [Formula 63] [Formula 64] [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]

[Formula 97] [Formula 98] [Formula 99] [Formula 100]

[Formula 101] [Formula 102] [Formula 103] [Formula 104]

[Formula 105] [Formula 106] [Formula 107] [Formula 108]

[Formula 109] [Formula 110] [Formula 111] [Formula 112]

[Formula 113] [Formula 114] [Formula 115] [Formula 116]

[Formula 117] [Formula 118] [Formula 119] [Formula 120]

[Formula 121] [Formula 122] [Formula 123] [Formula 124]

[Formula 125] [Formula 126] [Formula 127] [Formula 128]

[Formula 129] [Formula 130] [Formula 131] [Formula 132]

[Formula 133] [Formula 134] [Formula 135] [Formula 136]

[Formula 137] [Formula 138] [Formula 139] [Formula 140]

[Formula 141] [Formula 142] [Formula 143] [Formula 144]

[Formula 145] [Formula 146] [Formula 147] [Formula 148]

[Formula 149] [Formula 150] [Formula 151] [Formula 152]

[Formula 153] [Formula 154] [Formula 155] [Formula 156]

[Formula 157] [Formula 158] [Formula 159] [Formula 160]

[Formula 161] [Formula 162] [Formula 163] [Formula 164]

[Formula 165] [Formula 166] [Formula 167] [Formula 168]

[Formula 169] [Formula 170] [Formula 171] [Formula 172]

[Formula 173] [Formula 174] [Formula 175] [Formula 176]

[Formula 177] [Formula 178] [Formula 179] [Formula 180]

[Formula 181] [Formula 182] [Formula 183] [Formula 184]

[Formula 185] [Formula 186] [Formula 187] [Formula 188]

[Formula 189] [Formula 190] [Formula 191] [Formula 192]

[Formula 193] [Formula 194] [Formula 195] [Formula 196]

[Formula 197] [Formula 198] [Formula 199] [Formula 200]

[Formula 201] [Formula 202] [Formula 203] [Formula 204]

[Formula 205] [Formula 206] [Formula 207] [Formula 208]

[Formula 209] [Formula 210] [Formula 211] [Formula 212]

[Formula 213] [Formula 214] [Formula 215] [Formula 216]

[Formula 217] [Formula 218] [Formula 219] [Formula 220]

[Formula 221] [Formula 222] [Formula 223] [Formula 224] Anode; Cathode; Or an organic electroluminescent device comprising a layer comprising the aromatic compound according to claim 1 between the anode and the cathode. The organic light emitting device of claim 3, wherein the aromatic compound is included in a light emitting layer between the anode and the cathode. The organic material of claim 4, further comprising at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer, and an electron injection layer between the anode and the cathode. Electroluminescent element. The organic light emitting device of claim 3, wherein the organic light emitting display device is used for a display device, a display device, and a monochrome or white illumination device.

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