KR101256205B1 - Organic light emitting compound and organic light emitting device comprising the same - Google Patents

Abstract

상기 화학식 I에서, A, B₁, B₂, B₃, R₁, R₂ 및 R₃는 발명의 상세한 설명을 참조한다.An organic light emitting compound represented by formula (I) is disclosed:
(I)

In the above formula (I), A, B ₁ , B ₂ , B ₃ , R ₁ , R ₂ and R ₃ refer to the detailed description of the invention.

Description

Organic light emitting compound and organic light emitting device comprising the same

The present invention relates to an organic light emitting compound and an organic light emitting device having the same. It is about.

The light emitting device is a self-luminous device, and has a wide viewing angle, excellent contrast, and fast response time. The light emitting device is classified into an inorganic light emitting device using an inorganic compound and an organic light emitting device (OLED) using an organic compound in an emitting layer. The organic light emitting device is a subject of much research in that it is excellent in physical properties such as high luminance, low driving voltage, short response speed, and multicolored, compared to the inorganic light emitting device.

The organic light emitting device generally has a stack structure of anode / organic light emitting layer / cathode, and includes anode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode or anode / hole injection layer / hole transport layer / light emitting layer / It may have various structures such as a hole blocking layer / electron transport layer / electron injection layer / cathode.

In order to realize an organic light emitting device having high luminous efficiency and long operating life, a high performance organic light emitting compound is important.

Therefore, a light emitting material having high luminous efficiency and luminous luminance is required.

The first technical challenge is to provide new organic light emitting compounds.

The second technical problem is to provide an organic light emitting device having improved luminous efficiency and luminous brightness.

According to one aspect, an organic light emitting compound represented by the following formula (I) is provided.

<Formula I>

In Formula I,

A is CH or N;

B ₁ , B ₂ and B ₃ are each independently a covalent bond, a phenylene group, a biphenylene group or a 9,9'-spirobifluorenylene group,

,

, 카바졸릴기, N-(C₁-C₅알킬)카바졸릴기, N-(C₆-C₂₀아릴)카바졸릴기, 치환 또는 비치환된 트리아졸기, 9,9'-디(C₁-C₅알킬)실라플루오레닐기, 9,9'-디(C₆-C₂₀아릴)실라플루오레닐기, 디벤조티오페닐기, 트리페닐레닐기, 9,9'-스파이로바이플루오레닐기 또는 페닐기이며,R ₁ , R ₂ and R ₃ are independently of each other

,

, Carbazolyl group, N- (C ₁ -C ₅ alkyl) carbazolyl group, N- (C ₆ -C ₂₀ aryl) carbazolyl group, substituted or unsubstituted triazole group, 9,9'-di (C ₁ -C ₅ alkyl) silafluorenyl group, 9,9'-di (C ₆ -C ₂₀ aryl) silafluorenyl group, dibenzothiophenyl group, triphenylenyl group, 9,9'-spirobifluorenyl group Or a phenyl group,

CY1, CY2, CY3 are each independently a substituted or unsubstituted C ₆ -C ₅₀ aromatic ring, or a substituted or unsubstituted C ₂ -C ₅₀ heteroaromatic ring,

Provided that R ₁ , R ₂ and R ₃ are not a phenyl group at the same time.

According to another aspect, the first electrode; A second electrode; And an organic light emitting device including at least one organic film between the first electrode and the second electrode, wherein the organic film includes an organic light emitting compound as described above.

An organic light emitting device having a new organic light emitting compound according to one aspect improves luminous efficiency and luminous luminance.

1A to 1C are cross-sectional views schematically illustrating structures of one embodiment of an organic light emitting diode according to the present invention.

Hereinafter, an organic light emitting compound and an organic light emitting device having the same according to at least one exemplary embodiment will be described in more detail.

In the present specification, the organic light emitting compound is a compound used in an organic light emitting device, which is not necessarily limited to a compound capable of emitting light, and its application range is not limited to the organic light emitting layer, and includes a hole injection layer, a hole transport layer, and an electron injection. All of the layers constituting the organic light emitting device such as the layer and the electron transport layer can be used.

An organic light emitting compound according to one embodiment is represented by Formula I:

<Formula I>

In Formula I,

A is CH or N;

B ₁ , B ₂ and B ₃ are each independently a covalent bond, a phenylene group, a biphenylene group or a 9,9'-spirobifluorenylene group,

,

, 카바졸릴기, N-(C₁-C₅알킬)카바졸릴기, N-(C₆-C₂₀아릴)카바졸릴기, 치환 또는 비치환된 트리아졸기, 9,9'-디(C₁-C₅알킬)실라플루오레닐기, 9,9'-디(C₆-C₂₀아릴)실라플루오레닐기, 디벤조티오페닐기, 트리페닐레닐기, 9,9'-스파이로바이플루오레닐기 또는 페닐기이며,R ₁ , R ₂ and R ₃ are independently of each other

,

, Carbazolyl group, N- (C ₁ -C ₅ alkyl) carbazolyl group, N- (C ₆ -C ₂₀ aryl) carbazolyl group, substituted or unsubstituted triazole group, 9,9'-di (C ₁ -C ₅ alkyl) silafluorenyl group, 9,9'-di (C ₆ -C ₂₀ aryl) silafluorenyl group, dibenzothiophenyl group, triphenylenyl group, 9,9'-spirobifluorenyl group Or a phenyl group,

CY1, CY2, CY3 are each independently a substituted or unsubstituted C ₆ -C ₅₀ aromatic ring, or a substituted or unsubstituted C ₂ -C ₅₀ heteroaromatic ring,

Provided that R ₁ , R ₂ and R ₃ are not a phenyl group at the same time.

The compound represented by Chemical Formula I is suitable as a material forming an organic film interposed between the first electrode and the second electrode of the organic light emitting device. The compound of formula (I) is suitable for use in organic membranes of organic light emitting devices, especially light emitting layers, hole injection layers, hole transport layers or electron transport layers, and may be used as a phosphorescent host material as well as a dopant material. Compound represented by the formula (I) is excellent in life characteristics.

The aromatic ring is a divalent to 10-valent group having an aromatic ring system, and may include two or more ring systems, and the two or more ring systems may exist in a bonded or fused form with each other. The heteroaromatic ring refers to a group in which at least one carbon of the aromatic ring is substituted with at least one selected from the group consisting of N, O, S and P.

More specifically, the CY1, CY2, CY3 are independently of each other, benzene, N- (C ₆ -C ₂₀ aryl) carbazole, 9,9'-di (C ₁ -C ₅ alkyl) fluorene, dibenzoti Offen, 9,9'-di (C ₁ -C ₅ alkyl) silafluorene, 1,1'-di (C ₁ -C ₅ alkyl) indene, N- (C ₆ -C ₂₀ aryl) indole, indolo It may be an aromatic or heteroaromatic ring derived from a compound selected from the group consisting of carbazole and derivatives thereof.

When the triazole group, aromatic ring, heteroaromatic ring is substituted, the substituents of the triazole group, aromatic ring, heteroaromatic ring are independently of each other C ₁ -C ₅₀ alkyl group; C ₆ -C ₅₀ aryl groups unsubstituted or substituted with C ₁ -C ₅₀ alkyl groups; And a C ₂ -C ₅₀ heteroaryl group which is unsubstituted or substituted with a C ₁ -C ₅₀ alkyl group.

More specifically, the organic light emitting compound may have a structure of Formula 1 to 55, but is not limited thereto:

&Lt; Formula 1 > < EMI ID =

&Lt; Formula 3 > < Formula 4 >

&Lt; Formula 5 > < EMI ID =

<Formula 7> <Formula 8>

<Formula 9> <Formula 10>

<Formula 11> <Formula 12>

<Formula 13> <Formula 14>

<Formula 15> <Formula 16>

<Formula 17> <Formula 18>

&Lt; Formula 19 > < EMI ID =

<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>

The organic light emitting compound represented by Chemical Formula I may be synthesized using a conventional synthetic method, and for a more detailed synthetic route of the compound, see Scheme of Synthesis Example below.

An organic light emitting device according to another embodiment, the first electrode; A second electrode; And an organic layer interposed between the first electrode and the second electrode, wherein the organic layer includes at least one compound represented by Formula (I).

<Formula I>

,

, 카바졸릴기, N-(C₁-C₅알킬)카바졸릴기, N-(C₆-C₂₀아릴)카바졸릴기, 치환 또는 비치환된 트리아졸기, 9,9'-디(C₁-C₅알킬)실라플루오레닐기, 9,9'-디(C₆-C₂₀아릴)실라플루오레닐기, 디벤조티오페닐기, 트리페닐레닐기, 9,9'-스파이로바이플루오레닐기 또는 페닐기이며, CY1, CY2, CY3가 서로 독립적으로 치환 또는 비치환된 C₆-C₅₀방향족 고리, 또는 치환 또는 비치환된 C₂-C₅₀헤테로방향족 고리이며, 단, R₁, R₂ 및 R₃가 동시에 페닐기가 아니다.
In formula (I), A is CH or N; B ₁ , B ₂ and B ₃ are independently of each other a covalent bond, a phenylene group, a biphenylene group or a 9,9'-spirobifluorenylene group, and R ₁ , R ₂ and R ₃ are independently of each other

,

, Carbazolyl group, N- (C ₁ -C ₅ alkyl) carbazolyl group, N- (C ₆ -C ₂₀ aryl) carbazolyl group, substituted or unsubstituted triazole group, 9,9'-di (C ₁ -C ₅ alkyl) silafluorenyl group, 9,9'-di (C ₆ -C ₂₀ aryl) silafluorenyl group, dibenzothiophenyl group, triphenylenyl group, 9,9'-spirobifluorenyl group Or a phenyl group, and CY1, CY2, CY3 are each independently a substituted or unsubstituted C ₆ -C ₅₀ aromatic ring, or a substituted or unsubstituted C ₂ -C ₅₀ heteroaromatic ring, provided that R ₁ , R ₂ and R ₃ is not a phenyl group at the same time.

The compound of formula (I) is suitable for use in organic membranes of organic light emitting devices, in particular in light emitting layers, hole injection layers, hole transport layers, electron injection layers or electron transport layers.

The structure of the organic light emitting device according to another embodiment is very diverse. The organic EL device may further include at least one layer selected from the group consisting of a hole injecting layer, a hole transporting layer, a hole blocking layer, an electron blocking layer, an electron transporting layer, and an electron injecting layer between the first electrode and the second electrode.

More specifically, the embodiment of the organic light emitting device refer to Figures 1a, 1b and 1c. The organic light emitting device of Figure 1a has a structure consisting of a first electrode / hole injection layer / light emitting layer / electron transport layer / electron injection layer / second electrode, the organic light emitting device of Figure 1b has a first electrode / hole injection layer / hole transport layer / Light emitting layer / electron transport layer / electron injection layer / second electrode. In addition, the organic light emitting device of FIG. 1C has a structure of a first electrode / hole injection layer / hole transport layer / light emitting layer / hole blocking layer / electron transport layer / electron injection layer / second electrode. At this time, one or more of the light emitting layer, the hole injection layer and the hole transport layer may include a compound represented by the formula (I).

The emission layer of the organic light emitting diode may include a phosphorescent or fluorescent dopant including red, green, blue, or white. Among these, the phosphorescent dopant may be an organometallic compound including at least one element selected from the group consisting of Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, and Tm. In addition, the compound represented by Formula I may be used as a fluorescent host, fluorescent dopant, phosphorescent host or phosphorescent dopant in the light emitting layer.

A method of manufacturing an organic light emitting diode according to another embodiment will be described with reference to the organic light emitting diode illustrated in FIG. 1C.

First, a first electrode material having a high work function on the substrate is disposed by a deposition method or a sputtering method to form a first electrode. The first electrode may be an anode. Herein, a substrate used in a conventional organic light emitting device is used, but a glass substrate or a transparent plastic substrate having excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and waterproofness is preferable. As the first electrode material, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO 2), zinc oxide (ZnO), and the like, which are transparent and have excellent conductivity, may be used.

Next, a hole injection layer HIL may be formed on the first electrode by using various methods such as vacuum deposition, spin coating, casting, and LB.

In the case of forming the hole injection layer by vacuum deposition, the deposition conditions vary depending on the compound used as the material of the hole injection layer, the structure and thermal properties of the hole injection layer, and the like. It is preferable that a vacuum degree of 10 ^-8 to 10 ^-3 torr, a deposition rate of 0.01 to 100 Pa / sec, and a film thickness are appropriately selected in the range of usually 100 Pa to 10 µm.

When the hole injection layer is formed by the spin coating method, the coating conditions vary depending on the compound used as the material of the hole injection layer, the structure and the thermal properties of the desired hole injection layer, but the coating speed is preferably from about 2000 rpm to 5000 rpm , And the heat treatment temperature for removing the solvent after coating is suitably selected within a temperature range of about 80 캜 to 200 캜.

The hole injection layer material may be a compound represented by Formula (I) as described above. Or phthalocyanine compounds such as copper phthalocyanine disclosed in US Pat. No. 4,356,429 or the starburst type amine derivatives described in Advanced Material, 6, p.677 (1994), for example, TCTA, m-MTDATA, m-. MTDAPB, 2-TNATA (4,4 ', 4 "-tris (N- (2-naphtyl) -N-phenylamino) triphenylamine: 4,4', 4" -tris (N- (naphthyl) -N-phenyl Amino) triphenylamine), DNTPD (4,4'-bis- (N- {4- [N '-(3-methylphenyl-N'-phenylamino] phenyl) -N-phenylamino) biphenyl}, soluble conductivity Polymer Pani / DBSA (Polyaniline / Dodecylbenzenesulfonic acid: polyaniline / dodecylbenzenesulfonic acid) or PEDOT / PSS (Poly (3,4-ethylenedioxythiophene) / Poly (4-styrenesulfonate): poly (3,4-ethylenedioxythiophene) Poly (4-styrenesulfonate)), PANI / CSA (Polyaniline / Camphor sulfonicacid: polyaniline / camphorsulfonic acid) or PANI / PSS (Polyaniline) / Poly (4-styrenesulfonate): polyaniline) / poly (4-styrenesulfonate Known hole injection materials such as It can be used.

PANI / DBSA PEDOT / PSS

The thickness of the hole injection layer may be about 100 Å to 10000 Å, preferably 100 Å to 1000 Å. This is because when the thickness of the hole injection layer is less than 100 kV, the hole injection characteristic may be lowered, and when the thickness of the hole injection layer exceeds 10000 kV, the driving voltage may increase.

Next, a hole transport layer (HTL) may be formed on the hole injection layer by using various methods such as vacuum deposition, spin coating, cast, and LB. In the case of forming the hole transporting layer by the vacuum deposition method and the sputtering method, the deposition conditions and the coating conditions vary depending on the compound used, but are generally selected from substantially the same range of conditions as the formation of the hole injection layer.

The hole transport layer material may comprise a compound of formula (I) as described above. Alternatively, for example, carbazole derivatives such as N-phenylcarbazole, polyvinylcarbazole, N, N'-bis (3-methylphenyl) -N, N'-diphenyl- [1,1-biphenyl ] 4,4'-diamine (TPD), N, N'-di (naphthalen-1-yl) -N, N'-diphenyl benzidine (α-NPD), and other conventional amine derivatives having aromatic condensed rings Known hole transport materials such as the like may be used.

The hole transport layer may have a thickness of about 50 kPa to 1000 kPa, preferably 100 kPa to 600 kPa. When the thickness of the hole transporting layer is less than 50 Å, the hole transporting property may be degraded. When the thickness of the hole transporting layer is more than 1000 Å, the driving voltage may increase.

Next, the light emitting layer EML may be formed on the hole transport layer by using a vacuum deposition method, a spin coating method, a cast method, an LB method, or the like. When the light emitting layer is formed by the vacuum deposition method or the spin coating method, the deposition conditions vary depending on the compound used, but are generally selected from the ranges of conditions substantially the same as those of forming the hole injection layer.

The light emitting layer may include the compound represented by Formula I as described above. At this time, it may be used with a known host material suitable for the compound of the formula (I), or may be used with a known dopant material. It is also possible to use the compounds of formula (I) alone. For host materials, for example, Alq3 (tris (8-hydroxy-quinolatealuminium) or CBP (4,4'-N, N'-dicarbazole-biphenyl), or PVK (poly (n-vinylcarbazole) ) Can be used.

PVK

In the case of the dopant material, as the fluorescent dopant, IDE102, IDE105, and C545T, available from Hayashibara, can be used. Ir (PPy) 3 (PPy = 2-phenylpyridine), F 2 Irpic which is a blue phosphorescent dopant, a red phosphorescent dopant RD 61 manufactured by UDC, and the like can be used. MQD (N-methylquinacridone), coumarine derivatives and the like can also be used. Doping concentration is not particularly limited, but the content of the dopant is generally 0.01 to 15 parts by weight based on 100 parts by weight of the host.

The thickness of the light emitting layer may be about 100 Å to 1000 Å, preferably 200 Å to 600 Å. When the thickness of the light emitting layer is less than 100 Å, the light emitting characteristics may be degraded. If the thickness of the light emitting layer is more than 1000 Å, the driving voltage may increase.

When a light emitting compound is used with a phosphorescent dopant in the light emitting layer, a method such as vacuum deposition, spin coating, cast method, LB method, etc. is used on the light emitting layer to prevent the triplet excitons or holes from diffusing into the electron transport layer. The hole blocking layer HBL can be formed. In the case of forming the hole blocking layer by the vacuum deposition method and the spin coating method, the conditions vary depending on the compound used, but are generally selected from substantially the same range of conditions as the formation of the hole injection layer. Known hole blocking materials that can be used include, for example, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, and BCP.

The hole blocking layer may have a thickness of about 50 kPa to 1000 kPa, preferably 100 kPa to 300 kPa. This is because when the thickness of the hole blocking layer is less than 50 kV, the hole blocking property may be deteriorated. When the thickness of the hole blocking layer is more than 1000 kV, the driving voltage may increase.

When the hole blocking layer is omitted, an organic light emitting device having the structure shown in FIG. 1A is obtained.

Next, an electron transport layer (ETL) is formed by various methods such as a vacuum evaporation method, a spin coating method, and a casting method. In the case of forming the electron transporting layer by the vacuum deposition method and the spin coating method, the conditions vary depending on the compound used, but generally, the conditions are substantially the same as those for forming the hole injection layer. For example, the compound of formula I may be used in the electron transport layer. The electron transport layer material functions to stably transport electrons injected from an electron injection electrode (Cathode), and a quinoline derivative, particularly a known material such as tris (8-quinolinorate) aluminum (Alq3), TAZ, Balq, etc. Can also be used.

PBD

The electron transport layer may have a thickness of about 100 kPa to 1000 kPa, preferably 200 kPa to 500 kPa. When the thickness of the electron transporting layer is less than 100 angstroms, the electron transporting characteristics may be deteriorated. When the thickness of the electron transporting layer exceeds 1000 angstroms, the driving voltage may increase.

Further, an electron injection layer (EIL), which is a material having a function of facilitating the injection of electrons from the cathode, may be laminated on the electron transporting layer, which is not particularly limited.

As the electron injection layer, any material known as an electron injection layer forming material such as LiF, NaCl, CsF, Li 2 O, BaO or the like can be used. The deposition conditions of the electron injection layer vary depending on the compound used, but are generally selected from substantially the same range of conditions as the formation of the hole injection layer.

The thickness of the electron injection layer may be about 1 A to 100 A, preferably 5 A to 50 A. This is because, when the thickness of the electron injection layer is less than 1 kW, the electron injection characteristic may be deteriorated, and when the thickness of the electron injection layer exceeds 100 kW, the driving voltage may increase.

Finally, the second electrode may be formed on the electron injection layer by using a vacuum deposition method or a sputtering method. The second electrode may be used as a cathode. As the metal for forming the second electrode, a metal, an alloy, an electrically conductive compound having a low work function, and a mixture thereof may be used. Specific examples include lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), and the like. Can be mentioned. In addition, a transmissive cathode using ITO and IZO may be used to obtain the front light emitting device.

Hereinafter, Synthesis Examples and Examples of the present invention will be specifically described, but the present invention is not limited to the following Synthesis Examples and Examples.

[Synthesis Example 1] Synthesis of compound [1]

5.0 g (19.55 mmol) of 3-chloro-4,5-diphenyl-4H-1,2,4-triazole, 3.27 g (19.55 mmol) of 9H-carbazole, 372 mg of copper iodide in a 250 mL round bottom flask (1.95 mmol), 8.30 g (39.1 mmol) of potassium phosphate (K ₃ PO ₄ ), and 1.96 mL (29.33 mmol) of 1,2-ethylenediamine were added thereto, and the mixture was stirred at reflux for 12 hours at 120 ° C. with 150 mL of toluene under a nitrogen stream. And reacted.

After the reaction was completed, the reaction solution was cooled to room temperature, and the reaction solution was poured into 200 mL of diluted aqueous hydrochloric acid solution to separate the layers. The organic layer was separated and washed with 200 mL saturated brine. The washed organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and then recrystallized from dichloromethane and methanol to obtain 4.5 g (60%) of the title compound [1] as a white solid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 8.50 (d, 1H), 8.15 (m, 2H), 8.10 (m, 2H), 7.65 ~ 7.20 (m, 13H)

MS / FAB: 386 (M ⁺ )

[Synthesis Example 2] Synthesis of compound [2]

Target compound [2] 6.5 using 3-chloro-4,5-diphenyl-4H-1,2,4-triazole 5.0 g (19.55 mmol) and compound [2-1] in the same manner as in Synthesis example 1 g (60%) was obtained.

¹ H NMR (300 MHz, CDCl ₃ ): δ 8.49 (d, 2H), 8.20 (m, 2H), 7.95m, 2H), 7.61 ~ 7.23 (m, 19H)

MS / FAB: 551 (M ⁺ )

[Synthesis Example 3] Synthesis of compound [3]

Target compound [3] 5.5 using 5.0 g (19.55 mmol) of 3-chloro-4,5-diphenyl-4H-1,2,4-triazole and compound [3-1] in the same manner as in Synthesis example 1 5.5 g (51%) was obtained.

¹ H NMR (300 MHz, CDCl ₃ ): δ 8.51 (m, 2H), 8.25 (m, 2H), 8.10 (d, 1H), 7.90 (m, 2H), 7.61 ~ 7.21 (m, 18H)

MS / FAB: 551 (M ⁺ )

[Synthesis Example 4] Synthesis of compound [4]

Target compound [4] 7.0 using 3-chloro-4,5-diphenyl-4H-1,2,4-triazole 5.0 g (19.55 mmol) and compound [4-1] in the same manner as in Synthesis example 1 7.0 g (65%) was obtained.

¹ H NMR (300 MHz, CDCl ₃ ): δ 8.54 (d, 1H), 8.25 (m, 2H), 8.10 (m, 2H), 7.65 ~ 7.20 (m, 20H)

MS / FAB: 551 (M ⁺ )

[Synthesis Example 5] Synthesis of compound [5]

Target compound [5] 5.1 using 3-chloro-4,5-diphenyl-4H-1,2,4-triazole 5.0 g (19.55 mmol) and compound [5-1] in the same manner as in Synthesis example 1 5.1 g (52%) was obtained.

¹ H NMR (300 MHz, CDCl ₃ ): δ 8.55 (d, 1H), 8.25 (m, 2H), 8.10 ~ 8.00 (m, 3H), 7.75 (d, 1H), 7.60 ~ 7.21 (m, 13H) , 1.75 (s, 6H)

MS / FAB: 502 (M ⁺ )

[Synthesis Example 6] Synthesis of compound [6]

Target compound [6] 6.7 using 5.0 g (19.55 mmol) of 3-chloro-4,5-diphenyl-4H-1,2,4-triazole and compound [6-1] in the same manner as in Synthesis example 1 g (68%) was obtained.

¹ H NMR (300 MHz, CDCl ₃ ): δ 8.51 (d, 1H), 8.27 (m, 2H), 8.11 (m, 2H), 7.95 (d, 1H), 7.64 ~ 7.23 (m, 14H)

MS / FAB: 502 (M ⁺ )

Synthesis Example 7 Synthesis of Compound [7]

Using the same method as in Synthesis Example 1, 5.0 g (19.55 mmol) of 3-chloro-4,5-diphenyl-4H-1,2,4-triazole and Compound [7-1] were used as the target compound [7] 5.7 g (59%) was obtained.

¹ H NMR (300 MHz, CDCl ₃ ): δ 8.50 (m, 2H), 8.27 (m, 2H), 8.10 to 8.00 (m, 3H), 7.60 to 7.20 (m, 13H)

MS / FAB: 492 (M ⁺ )

[Synthesis Example 8] Synthesis of compound [8]

Target compound [8] 5.1 using 3-chloro-4,5-diphenyl-4H-1,2,4-triazole 5.0 g (19.55 mmol) and compound [8-1] in the same manner as in Synthesis example 1 g (53%) was obtained.

¹ H NMR (300 MHz, CDCl ₃ ): δ 8.50 (m, 2H), 8.29 (m, 2H), 7.99 ~ 7.90 (m, 3H), 7.62 ~ 7.23 (m, 13H)

MS / FAB: 492 (M ⁺ )

[Synthesis Example 9] Synthesis of compound [9]

Target compound [9] 6.3 using 5.0 g (19.55 mmol) of 3-chloro-4,5-diphenyl-4H-1,2,4-triazole and compound [9-1] in the same manner as in Synthesis example 1 g (65%) was obtained.

¹ H NMR (300 MHz, CDCl ₃ ): δ 8.51-8.49 (m, 2H), 8.25 (m, 2H), 7.95 (m, 2H), 7.80 (s, 2H), 7.55-7.24 (m, 12H)

MS / FAB: 492 (M ⁺ )

[Synthesis Example 10] Synthesis of Compound [10]

Target compound [10] 5.9 using 5.0 g (19.55 mmol) of 3-chloro-4,5-diphenyl-4H-1,2,4-triazole and compound [10-1] in the same manner as in Synthesis example 1 g (58%) was obtained.

¹ H NMR (300 MHz, CDCl ₃ ): δ 8.56 (d, 1H), 8.30 (m, 3H), 7.90 (m, 3H), 7.63 ~ 7.23 (m, 13H), 0.65 (s, 6H)

MS / FAB: 518 (M ⁺ )

[Synthesis Example 11] Synthesis of compound [11]

Using the same method as in Synthesis Example 1, 5.0 g (19.55 mmol) of 3-chloro-4,5-diphenyl-4H-1,2,4-triazole and compound [11-1] were used as the target compound [11] 6.9 g (68%) was obtained.

¹ H NMR (300 MHz, CDCl ₃ ): δ 8.57 (d, 1H), 8.25 (m, 2H), 7.91 (m, 3H), 7.70 (s, 1H), 7.65 ~ 7.27 (m, 13H), 0.66 (s, 6H)

MS / FAB: 518 (M ⁺ )

[ Synthetic example  12] Synthesis of Compound [12]

6.1 g of the target compound [12] using 3-chloro-4,5-diphenyl-4H-1,2,4-triazole 5.0 g (19.55 mmol) and compound [12-1] in the same manner as in Synthesis example 1. g (51%) was obtained.

¹ H NMR (300 MHz, CDCl ₃ ): δ 8.53 (s, 1H), 8.47 (m, 2H), 8.12 to 8.07 (m, 3H), 7.74 to 7.71 (m, 2H), 7.62 to 7.41 (m, 12H), 7.26 ~ 7.21 (m, 2H), 1.72 (s, 12H)

MS / FAB: 618 (M ⁺ )

[Synthesis Example 13] Synthesis of compound [13]

Using the same method as in Synthesis Example 1, 5.0 g (19.55 mmol) of 3-chloro-4,5-diphenyl-4H-1,2,4-triazole and compound [13-1] were used as the target compound [13] 6.7 g (56%) was obtained.

¹ H NMR (300 MHz, CDCl ₃ ): δ 8.83 (s, 1H), 8.45 (m, 2H), 8.15 ~ 8.09 (m, 3H), 7.65 ~ 7.43 (m, 14H), 7.25 ~ 7.21 (m, 2H), 1.72 (s, 12H)

MS / FAB: 618 (M ⁺ )

[Synthesis Example 14] Synthesis of compound [14]

Target compound [14] 6.0 using 3-chloro-4,5-diphenyl-4H-1,2,4-triazole 5.0 g (19.55 mmol) and compound [14-1] in the same manner as in Synthesis example 1. g (62%) was obtained.

¹ H NMR (300 MHz, CDCl ₃ ): δ 8.56 ~ 8.54 (m, 2H), 8.39 ~ 8.36 (m, 2H), 8.11 ~ 8.07 (m, 2H), 7.66 ~ 7.24 (m, 17H)

MS / FAB: 501 (M ⁺ )

[Synthesis Example 15] Synthesis of compound [15]

Target compound [15] 5.7 using 3-chloro-4,5-diphenyl-4H-1,2,4-triazole 5.0 g (19.55 mmol) and compound [15-1] in the same manner as in Synthesis example 1 g (41%) was obtained.

¹ H NMR (300 MHz, CDCl ₃ ): δ 8.55 ~ 8.51 (m, 3H), 8.13 ~ 8.09 (m, 2H), 7.77 ~ 7.72 (m, 3H), 7.64 ~ 7.23 (m, 24H)

MS / FAB: 716 (M ⁺ )

[Synthesis Example 16] Synthesis of compound [16]

In the same manner as in Synthesis Example 1, 6.3 g (59%) of the target compound [16] was obtained by using 5.0 g (19.63 mmol) of 2-chloro-1,5-diphenyl-1H-imidazole and compound [3-1]. Obtained.

¹ H NMR (300 MHz, CDCl ₃ ): δ 8.56 ~ 8.54 (m, 2H), 8.13 ~ 8.10 (m, 3H), 7.75 ~ 7.71 (m, 2H), 7.67 ~ 7.22 (m, 19H)

MS / FAB: 550 (M ⁺ )

[Synthesis Example 17] Synthesis of Compound [17]

In the same manner as in Synthesis Example 1, 6.8 g (63%) of the target compound [17] was obtained by using 5.0 g (19.63 mmol) of 5-chloro-1,2-diphenyl-1H-imidazole and compound [3-1]. Obtained.

¹ H NMR (300 MHz, CDCl ₃ ): δ 8.56 ~ 8.54 (m, 2H), 8.15 ~ 8.11 (m, 3H), 7.74 ~ 7.70 (m, 2H), 7.65 ~ 7.24 (m, 19H)

MS / FAB: 550 (M ⁺ )

[Synthesis Example 18] Synthesis of Compound [18]

4.3 g (46%) of the target compound [18] using 5.0 g (15.11 mmol) of 2-chloro-1,4,5-triphenyl-1H-imidazole and compound [3-1] in the same manner as in Synthesis example 1. ) Was obtained.

¹ H NMR (300 MHz, CDCl ₃ ): δ 8.55 ~ 8.53 (m, 2H), 8.15 ~ 8.10 (m, 3H), 7.76 ~ 7.73 (m, 2H), 7.66 ~ 7.21 (m, 23H)

MS / FAB: 626 (M ⁺ )

[ Synthetic example  19] Synthesis of Compound [19]

[19-2] prepared using compound [19-1], n-butyllithium and trimethylborate prepared from 9H-carbazole and 1-bromo-3-iodobenzene in the same manner as in Synthesis example 1 Target compound using 3-chloro-4,5-diphenyl-4H-1,2,4-triazole 5.0 g (19.55 mmol), tetrakis (triphenylphosphite) palladium (II), potassium carbonate and toluene [19] 5.2 g (58%) were obtained.

¹ H NMR (300 MHz, CDCl ₃ ): δ 8.54 (d, 1H), 8.44-8.39 (m, 3H), 8.14-8.11 (m, 2H), 7.81 (d, 1H), 7.68-7.33 (m, 15H)

MS / FAB: 462 (M ⁺ )

[Synthesis Example 20] Synthesis of compound [20]

Compound [20-1] prepared from 9H-carbazole and 1-bromo-4-iodobenzene in the same manner as in Synthesis example 1, compound obtained using n-butyllithium and trimethylborate [20-2], Target compound using 3-chloro-4,5-diphenyl-4H-1,2,4-triazole 5.0 g (19.55 mmol), tetrakis (triphenylphosphite) palladium (II), potassium carbonate and toluene [20] 5.8 g (65%) were obtained.

¹ H NMR (300 MHz, CDCl ₃ ): δ 8.56 ~ 8.54 (m, 2H), 8.28 ~ 8.25 (m, 3H), 7.95 ~ 7.92 (m, 2H), 7.78 ~ 7.75 (m, 2H), 7.69 ~ 7.25 (m, 22)

MS / FAB: 627 (M ⁺ )

[Synthesis Example 21] Synthesis of Compound [21]

Compound [21-1] prepared from 9H-carbazole, 4-bromo-4'-iodobiphenyl, n-butyllithium and trimethylborate [21-2] in the same manner as in Synthesis example 1 ], 3-chloro-4,5-diphenyl-4H-1,2,4-triazole 5.0 g (19.55 mmol), tetrakis (triphenylphosphino) palladium (0), potassium carbonate and toluene 7.5 g (55%) of the title compound [21] were obtained.

¹ H NMR (300 MHz, CDCl ₃ ): δ 8.54 ~ 8.52 (m, 2H), 8.29 ~ 8.24 (m, 3H), 7.96 ~ 7.93 (m, 2H), 7.86 ~ 7.78 (m, 4H), 7.64 ~ 7.23 (m, 22 H)

MS / FAB: 703 (M ⁺ )

[Synthesis Example 22] Synthesis of compound [22]

Compound [22-1], n prepared from 11-phenyl-11,12-dihydroindolo [2,3-a] carbazole and 1-bromo-3-iodobenzene in the same manner as in Synthesis example 1 Compound [22-2] obtained using -butyllithium and trimethylborate, 5.0 g (19.55 mmol) of 3-chloro-4,5-diphenyl-4H-1,2,4-triazole, tetrakis (triphenyl Phosino) palladium (0), potassium carbonate and toluene were used to give 2.6 g (41%) of the desired compound [22].

¹ H NMR (300 MHz, CDCl ₃ ): δ 8.55 ~ 8.53 (m, 2H), 8.31 ~ 8.26 (m, 3H), 8.11 ~ 8.08 (m, 2H), 7.95 ~ 7.91 (m, 2H), 7.68 ~ 7.29 (m, 20 H)

MS / FAB: 627 (M ⁺ )

[Synthesis Example 23] Synthesis of compound [23]

5.15 g (11.7 mmol) of compound [23-1], 30 ml of toluene, 3 ml of water, tetrakis (triphenylphosphino) palladium (0) 0.47 g (1.17 mmol), and potassium carbonate 3.2 g ( 23.5 mmol) and 3.0 g (11.7 mmol) of 3-chloro-4,5-diphenyl-4H-1,2,4-triazole were obtained to obtain 3.2 g (47.1%) of the title compound [23] as a white solid. It was.

¹ H NMR (300 MHz, CDCl ₃ ): 8.06 (d, 1H), 7.61 (dd, 1H), 7.22 ~ 7.55 (m, 20H), 7.08 (t, 1H), 7.00 (t, 1H), 1.67 ( s, 6 H)

MS / FAB: 579 (M ⁺ )

[Synthesis Example 24] Synthesis of compound [24]

5.03 g (11.7 mmol) of intermediate compound [24-1], 30 ml of toluene, 3 ml of water, tetrakis (triphenylphosphino) palladium (0) 0.47 g (1.17 mmol) and potassium carbonate 3.2 g in the same manner as in Synthesis example 19 (23.5 mmol) and 3.0 g (11.7 mmol) of 3-chloro-4,5-diphenyl-4H-1,2,4-triazole were used to prepare 3.8 g (56.9%) of the target compound [24] as a white solid. Obtained.

¹ H NMR (300 MHz, CDCl ₃ ): 7.86 (d, 1H), 7.78 (m, 2H), 7.55 (d, 1H), 7.48 ~ 7.50 (m, 4H), 7.20 ~ 7.40 (m, 14H), 7.00 ~ 7.08 (m, 2H)

MS / FAB: 569 (M ⁺ )

[Synthesis Example 25] Synthesis of compound [25]

5.13 g (11.7 mmol) of an intermediate compound [25-1], 30 ml of toluene, 3 ml of water, tetrakis (triphenylphosphino) palladium (0) 0.47 g (1.17 mmol) and potassium carbonate 3.2 g in the same manner as in Synthesis example 19 (23.5 mmol) and 3.0 g (11.7 mmol) of 3-chloro-4,5-diphenyl-4H-1,2,4-triazole were used to prepare 2.7 g (39.8%) of the target compound [25] as a white solid. Obtained.

¹ H NMR (300 MHz, CDCl ₃ ): 7.54 (d, 1H), 7.55 (d, 1H), 7.48 ~ 7.50 (m, 4H), 7.20 ~ 7.40 (m, 17H), 7.00 ~ 7.08 (m, 4H )

MS / FAB: 578 (M ⁺ )

[Synthesis Example 26] Synthesis of compound [26]

Carbazole 2.22 g (13.3 mmol toluene 30 ml, copper iodide (I) copper 0.76 g (0.266 mmol), potassium phosphate 5.65 g (26.6 mmol), 1,2-ethylenediamine 0.16 g (2.66 mmol) and the same method as in Synthesis Example 1 4- (3'-bromophenyl) -3,5-diphenyl-4H-1,2,4-triazole [26-1] using 5.0 g (13.3 mmol) of the desired compound as a white solid [26] 2.2 g (35.8%) was obtained.

¹ H NMR (300 MHz, CDCl ₃ ): 7.57 (d, 1H), 7.55 (d, 1H), 7.48 (dd, 4H), 7.42 (d, 1H), 7.41 (d, 1H), 7.30 ~ 7.32 ( m, 8H), 7.22-7.73 (m, 2H), 7.00-7.08 (m, 4H)

MS / FAB: 463 (M ⁺ )

[Synthesis Example 27] Synthesis of compound [27]

2.22 g (13.3 mmol) of carbazole, 30 ml of toluene, 0.76 g (0.266 mmol) of copper (I) iodide, 5.65 g (26.6 mmol) of potassium phosphate, 0.16 g (2.66 mmol) of 1,2-ethylenediamine ) And the desired compound as a white solid using 5.0 g (13.3 mmol) of 4- (4'-bromophenyl) -3,5-diphenyl-4H-1,2,4-triazole [27-1] [ 27] 2.9 g (47.1%) were obtained.

¹ H NMR (300 MHz, CDCl ₃ ): 7.55 (d, 2H), 7.48 (d, 4H), 7.40 (d, 2H), 7.32 (td, 4H), 7.29 (d, 2H), 7.27 (d, 2H), 7.22 (td, 2H), 7.08 (td, 2H), 7.00 (td, 2H)

MS / FAB: 463 (M ⁺ )

[Synthesis Example 28] Synthesis of compound [28]

4.42 g (13.3 mmol) of intermediate compound [3-1], 30 ml of toluene, 0.76 g (0.266 mmol) of copper (I) iodide, 5.65 g (26.6 mmol) of potassium phosphate, 1,2-ethylene in the same manner as in Synthesis example 2 0.16 g (2.66 mmol) of diamine and 5.0 g (13.3 mmol) of 4- (3'-bromophenyl) -3,5-diphenyl-4H-1,2,4-triazole [26-1] 3.1 g (37.1%) of the title compound [28] was obtained as a white solid.

¹ H NMR (300 MHz, CDCl ₃ ): 7.48 ~ 7.55 (m, 7H), 7.22 ~ 7.32 (m, 17H), 7.05 ~ 7.10 (m, 4H), 7.00 (d, 1H)

MS / FAB: 628 (M ⁺ )

[Synthesis Example 29] Synthesis of compound [29]

4.42 g (13.3 mmol) of intermediate compound [4-1], 30 ml of toluene, 0.76 g (0.266 mmol) of copper (I) iodide, 5.65 g (26.6 mmol) of potassium phosphate, 1,2-ethylene in the same manner as in Synthesis example 1 0.16 g (2.66 mmol) of diamine and 5.0 g (13.3 mmol) of 4- (4'-bromophenyl) -3,5-diphenyl-4H-1,2,4-triazole [27-1] 3.0 g (35.9%) of the title compound [29] was obtained as a white solid.

¹ H NMR (300 MHz, CDCl ₃ ): 7.48-7.55 (m, 8H), 7.22-7.72 (m, 17H), 7.05-7.10 (m, 4H),

MS / FAB: 628 (M ⁺ )

[Synthesis Example 30] Synthesis of compound [30]

3.98 g (13.3 mmol) of intermediate compound [11-1], 30 ml of toluene, 0.76 g (0.266 mmol) of copper (I) iodide, 5.65 g (26.6 mmol) of potassium phosphate, 1,2-ethylene in the same manner as in Synthesis example 2 0.16 g (2.66 mmol) of diamine and 5.0 g (13.3 mmol) of 4- (3'-bromophenyl) -3,5-diphenyl-4H-1,2,4-triazole [26-1] 3.2 g (40.5%) of the title compound [30] was obtained as a white solid.

¹ H NMR (300 MHz, CDCl ₃ ): 7.89 (s, 1H), 7.72 (s, 1H), 7.60 (d, 1H), 7.58 (d, 1H), 7.55 (d, 1H), 7.22 ~ 7.48 ( m, 17H), 7.00-7.08 (m, 2H), 0.66 (s, 6H)

MS / FAB: 595 (M ⁺ )

[Synthesis Example 31] Synthesis of Compound [31]

5.31 g (13.3 mmol) of intermediate compound [13-1], 30 ml of toluene, 0.76 g (0.266 mmol) of copper (I) iodide, 5.65 g (26.6 mmol) of potassium phosphate, 1,2-ethylene in the same manner as in Synthesis example 2 0.16 g (2.66 mmol) of diamine and 5.0 g (13.3 mmol) of 4- (4'-bromophenyl) -3,5-diphenyl-4H-1,2,4-triazole [27-1] 3.8 g (41.1%) of the title compound [31] was obtained as a white solid.

¹ H NMR (300 MHz, CDCl ₃ ): 8.06 (d, 2H), 7.61 (d, 2H), 7.54 (s, 2H), 7.48 (s, 2H), 7.44-7.46 (m, 6H), 7.32 ( td, 4H), 7.32 (d, 2H), 7.30 (d, 2H), 7.26 (td, 2H), 7.22 (td, 2H), 1.67 (s, 12H)

MS / FAB: 695 (M ⁺ )

[Synthesis Example 32] Synthesis of compound [32]

3.77 g (13.3 mmol) of intermediate compound [6-1], 30 ml of toluene, 0.76 g (0.266 mmol) of copper (I) iodide, 5.65 g (26.6 mmol) of potassium phosphate, 1,2-ethylene in the same manner as in Synthesis example 1 0.16 g (2.66 mmol) of diamine and 5.0 g (13.3 mmol) of 4- (3'-bromophenyl) -3,5-diphenyl-4H-1,2,4-triazole [26-1] 3.5 g (45.5%) of the title compound [32] was obtained as a white solid.

¹ H NMR (300 MHz, CDCl ₃ ): 8.06 (d, 1H), 7.61 (d, 1H), 7.24-7.48 (m, 20H), 7.08 (td, 1H), 7.00 (td, 1H), 1.67 ( s, 6 H)

MS / FAB: 579 (M ⁺ )

[Synthesis Example 33] Synthesis of compound [33]

3.77 g (13.3 mmol) of intermediate compound [6-1], 30 ml of toluene, 0.76 g (0.266 mmol) of copper (I) iodide, 5.65 g (26.6 mmol) of potassium phosphate, 1,2-ethylene in the same manner as in Synthesis example 1 0.16 g (2.66 mmol) of diamine and 5.0 g (13.3 mmol) of 4- (4'-bromophenyl) -3,5-diphenyl-4H-1,2,4-triazole [27-1] 4.1 g (53.3%) of the title compound [33] was obtained as a white solid.

¹ H NMR (300 MHz, CDCl ₃ ): 8.08 (d, 1H), 7.33 ~ 7.40 (m, 21H), 7.10 ~ 7.12 (m, 2H), 1.68 (s, 6H)

MS / FAB: 579 (M ⁺ )

[ Synthetic example  34] Synthesis of Compound [34]

3.63 g (13.28 mmol) of intermediate compound [9-1] and 5 g of 4- (4-bromophenyl) -3,5-diphenyl-4H-1,2,4-triazole in the same manner as in Synthesis example 1 13.28 mmol) was used to obtain 4.1 g (55%) of the target compound of an off-white solid [34].

¹ H NMR (300 MHz, CDCl ₃ ): δ 8.50-8.45 (m, 2H), 8.30-8.28 (m, 4H), 7.98-7.94 (m, 2H), 7.86 (s, 1H), 7.78 (s, 1H), 7.64 ~ 7.62 (m, 4H), 7.52 ~ 7.25 (m, 10H)

MS / FAB: 568 (M ⁺ )

[Synthesis Example 35] Synthesis of compound [35]

3.63 g (13.28 mmol) of the intermediate compound [7-1] and 5 g of 4- (3-bromophenyl) -3,5-diphenyl-4H-1,2,4-triazole in the same manner as in Synthesis example 1 13.28 mmol) was obtained 4.0 g (53%) of the title compound [35] as an off-white solid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 8.50 ~ 8.45 (m, 2H), 8.30 ~ 8.28 (m, 4H), 8.05 ~ 7.94 (m, 3H), 7.52 ~ 7.25 (m, 15H)

MS / FAB: 568 (M ⁺ )

[Synthesis Example 36] Synthesis of compound [36]

Intermediate compound 5-phenyl-5,10-dihydroindo [3,2-b] indole 3.75 g (13.28 mmol) and 4- (3-bromophenyl) -3,5- in the same manner as in Synthesis example 1 5 g (13.28 mmol) of diphenyl-4H-1,2,4-triazole were used to obtain 3.9 g (51%) of the target compound as an off-white solid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 8.52 ~ 8.50 (m, 2H), 8.30 ~ 8.28 (m, 4H), 7.94 ~ 7.92 (m, 2H), 7.58 ~ 7.25 (m, 19H)

MS / FAB: 577 (M ⁺ )

[Synthesis Example 37] Synthesis of compound [37]

Intermediate compound 5-phenyl-5,10-dihydroindo [3,2-b] indole 3.75 g (13.28 mmol) and 4- (4-bromophenyl) -3,5- in the same manner as in Synthesis example 1 5 g (13.28 mmol) of diphenyl-4H-1,2,4-triazole were used to obtain 3.8 g (50%) of the target compound [37] as an off-white solid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 8.52 ~ 8.50 (m, 2H), 8.30 ~ 8.28 (m, 4H), 7.94 ~ 7.92 (m, 2H), 7.62 ~ 7.25 (m, 19H)

MS / FAB: 577 (M ⁺ )

[Synthesis Example 38] Synthesis of compound [38]

6.61 g (13.28 mmol) of an intermediate compound 5,10-diphenyl-10,15-dihydro-5H-diindoro [3,2-a: 3, '2'-c] carbazole in the same manner as in Synthesis example 1 ) And 4.4 g (42) of the target compound as an off-white solid using 5 g (13.28 mmol) of 4- (4-bromophenyl) -3,5-diphenyl-4H-1,2,4-triazole. %) Was obtained.

¹ H NMR (300 MHz, CDCl ₃ ): δ 8.50 ~ 8.45 (m, 3H), 8.30 ~ 8.28 (m, 4H), 7.94 ~ 7.92 (m, 3H), 7.62 ~ 7.25 (m, 26H)

MS / FAB: 792 (M ⁺ )

[Synthesis Example 39] Synthesis of compound [39]

4.58 g (15.94 mmol) of intermediate compound 9-phenyl-9H-carbazol-3-ylboronic acid and 4- (3-bromophenyl) -3,5-diphenyl-4H-1 in the same manner as in Synthesis example 19, 5 g (13.28 mmol) of 2,4-triazole were used to obtain 4.2 g (59%) of the target compound [39] as an off-white solid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 8.30-8.28 (m, 8H), 8.18-8.09 (m, 3H), 8.00 (d, 1H), 7.77 (s, 1H), 7.63-7.41 (m, 16H), 7.30-7.29 (m, 1H)

MS / FAB: 538 (M ⁺ )

[Synthesis Example 40] Synthesis of compound [40]

10 g (41.62 mmol) of N'-benzoylbenzohydrazide and 100 ml of 1,2-dichlorobenzene were added to a 100 mL round bottom flask, and the mixture was stirred in a nitrogen atmosphere. 36 g (332.97 mmol) of benzene-1,4-diamine and 25.5 g (166.48 mmol) of phosphoryl trichloride were added to the reaction solution, and the mixture was stirred under reflux at 160 ° C. for 12 hours. After completion of the reaction, the mixture was slowly cooled to room temperature, and the reaction solution was filtered. The filtered solid was washed with distilled water and methanol. The washed solid was stirred under reflux for 4 hours using 100 ml of acetone, filtered at 40 ° C., and then washed with acetone / n-hexane. The resultant was dried under vacuum at 100 ° C. to obtain 4.2 g (59%) of the target compound as an off-white solid. Obtained

¹ H NMR (300 MHz, CDCl ₃ ): δ 8.50-8.45 (m, 2H), 8.30-8.28 (m, 8H), 7.62-7.60 (m, 4H), 7.51-7.41 (m, 12H)

MS / FAB: 516 (M ⁺ )

[Synthesis Example 41] Synthesis of compound [41]

6.03 g (15.94 mmol) and 4- (3-bromophenyl) -3, intermediate compound 5,5-diphenyl-5H-dibenzo [b, d] silol-3-ylboronic acid in the same manner as in Synthesis example 19, 5 g (13.28 mmol) of 5-diphenyl-4H-1,2,4-triazole were used to obtain 5.1 g (62%) of the target compound [41] as an off-white solid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 8.30-8.28 (m, 4H), 8.09 (s, 1H), 7.95-7.89 (m, 2H), 7.82 (s, 1H), 7.61-7.35 (m, 23H)

MS / FAB: 629 (M ⁺ )

[Synthesis Example 42] Synthesis of compound [42]

3.64 g (15.94 mmol) of the intermediate compound dibenzo [b, d] thiophen-4-ylboronic acid and 4- (3-bromophenyl) -3,5-diphenyl-4H-1 in the same manner as in Synthesis example 19 5 g (13.28 mmol) of 2,4-triazole were used to obtain 3.8 g (60%) of the target compound [42] as an off-white solid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 8.45-8.41 (m, 2H), 8.30-8.22 (m, 5H), 8.09 (s, 1H), 7.98-7.97 (m, 1H), 7.58-7.41 ( m, 12H)

MS / FAB: 479 (M ⁺ )

[Synthesis Example 43] Synthesis of compound [43]

4.34 g (15.94 mmol) of the intermediate compound triphenylene-2-ylboronic acid and 4- (3-bromophenyl) -3,5-diphenyl-4H-1,2,4-tria in the same manner as in Synthesis example 19 5 g (13.28 mmol) of sol were used to obtain 4.2 g (61%) of the target compound [43] as an off-white solid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 8.60 (s, 1H), 8.53 to 8.52 (m, 2H), 8.30 to 8.28 (m, 4H), 8.18 to 8.04 (m, 5H), 7.88 to 7.82 ( m, 4H), 7.52-7.41 (m, 9H)

MS / FAB: 523 (M ⁺ )

[Synthesis Example 44] Synthesis of compound [44]

4.34 g (15.94 mmol) of the intermediate compound triphenylene-2-ylboronic acid and 4- (4-bromophenyl) -3,5-diphenyl-4H-1,2,4-tria in the same manner as in Synthesis example 19 5 g (13.28 mmol) of sol were used to obtain 4.3 g (62%) of the target compound [44] as an off-white solid.

¹ H NMR (300 MHz, CDCl ₃ ): δ 8.60 (s, 1H), 8.53 ~ 8.52 (m, 2H), 8.30 ~ 8.28 (m, 4H), 8.18 ~ 8.04 (m, 4H), 7.88 ~ 7.79 ( m, 6H), 7.68-7.57 (m, 2H), 7.51-7.41 (m, 6H)

MS / FAB: 523 (M ⁺ )

[ Synthetic example  45] Synthesis of Compound [45]

5 g (17.36 mmol) of dibenzo [b, d] thiophen-4-ylboronic acid and 4.4 g of 3-chloro-4,5-diphenyl-4H-1,2,4-triazole in the same manner as in Synthesis example 19 (17.36 mmol) was used to yield 3.9 g (56%) of the title compound [45] as an off-white solid.

¹ H NMR (300 MHz, CDCl ₃ ): 8.35-8.31 (m, 2H), 8.18 (d, 2H), 7.88 (d, 1H), 7.70 (d, 1H), 7.48-7.31 (m, 11H)

MS / FAB: 404 (M ⁺ )

[Synthesis Example 46] Synthesis of compound [46]

5 g (17.36 mmol) of dibenzo [b, d] thiophen-2-ylboronic acid and 4.4 g of 3-chloro-4,5-diphenyl-4H-1,2,4-triazole in the same manner as in Synthesis example 19 (17.36 mmol) was used to yield 3.8 g (54%) of the title compound [46] as an off-white solid.

¹ H NMR (300 MHz, CDCl ₃ ): 8.35 (d, 1H), 8.18 (d, 2H), 7.90 ~ 7.88 (m, 2H), 7.76 ~ 7.70 (m, 2H), 7.48 ~ 7.31 (m, 10H )

MS / FAB: 404 (M ⁺ )

[Synthesis Example 47] Synthesis of compound [47]

5 g (16.44 mmol) of 3- (dibenzo [b, d] thiophen-4-yl) phenylboronic acid and 3-chloro-4,5-diphenyl-4H-1,2, 4.2 g (16.44 mmol) of 4-triazole was used to obtain 4.8 g (61%) of the target compound [47] as an off-white solid.

¹ H NMR (300 MHz, CDCl ₃ ): 8.35 to 8.31 (m, 2H), 8.18 to 8.10 (m, 4H), 7.88 (d, 1H), 7.60 (s, 1H), 7.48 to 7.31 (m, 13H )

MS / FAB: 480 (M ⁺ )

[Synthesis Example 48] Synthesis of compound [48]

In the same manner as in Synthesis Example 19, 5 g (18.37 mmol) of triphenylene-2-ylboronic acid and 4.7 g (18.37 mmol) of 3-chloro-4,5-diphenyl-4H-1,2,4-triazole were used. This gave 4.3 g (52%) of the title compound [48] as an off-white solid.

¹ H NMR (300 MHz, CDCl ₃ ): 9.05 (s, 1H), 8.83 (d, 2H), 8.18 (d, 2H), 8.08 ~ 7.94 (m, 4H), 7.78 ~ 7.72 (m, 4H), 7.48 ~ 7.31 (m, 8H)

MS / FAB: 448 (M ⁺ )

[Synthesis Example 49] Synthesis of compound [49]

5 g (14.36 mmol) of 3- (triphenylen-2-yl) phenylboronic acid and 3.7 g of 3-chloro-4,5-diphenyl-4H-1,2,4-triazole in the same manner as in Synthesis example 19 (14.36 mmol) was used to yield 3.8 g (51%) of the target compound [49] as an off-white solid.

¹ H NMR (300 MHz, CDCl ₃ ): 9.05 (s, 1H), 8.83 (d, 2H), 8.18 ~ 7.94 (m, 7H), 7.78 ~ 7.72 (m, 4H), 7.60 (s, 1H), 7.48 ~ 7.31 (m, 10H)

MS / FAB: 524 (M ⁺ )

[Synthesis Example 50] Synthesis of compound [50]

5g (13.88mmol) and 3-chloro-4,5-diphenyl-4H-1,2,4-triazole 9,9'-spirobibi [florene] -2-ylboronic acid in the same manner as in Synthesis example 19 3.5 g (13.88 mmol) was used to obtain 4.2 g (57%) of the target compound [50] as an off-white solid.

¹ H NMR (300 MHz, CDCl ₃ ): 8.18 (d, 2H), 7.83 ~ 7.77 (m, 2H), 7.67 ~ 7.65 (m, 3H), 7.53 ~ 7.06 (m, 18H)

MS / FAB: 536 (M ⁺ )

[Synthesis Example 51] Synthesis of compound [51]

5 g (19.67 mmol) of 5,5-dimethyl-5H-dibenzo [b, d] silol-3-ylboronic acid and 3-chloro-4,5-diphenyl-4H-1,2 in the same manner as in Synthesis example 19 5 g (19.67 mmol) of, 4-triazole were used to obtain 4.6 g (54%) of the target compound [51] as an off-white solid.

¹ H NMR (300 MHz, CDCl ₃ ): 8.18 (d, 2H), 7.85 ~ 7.79 (m, 3H), 7.72 (s, 1H), 7.51 ~ 7.23 (m, 11H), 0.76 (s, 6H)

MS / FAB: 430 (M ⁺ )

[Synthesis Example 52] Synthesis of compound [52]

In the same manner as in Synthesis example 19, 5 g (13.22 mmol) of 5,5-diphenyl-5H-dibenzo [b, d] silol-3-ylboronic acid and 3-chloro-4,5-diphenyl-4H-1, 3.4 g (13.22 mmol) of 2,4-triazole were used to give 4.1 g (56%) of the target compound [52] as an off-white solid.

¹ H NMR (300 MHz, CDCl ₃ ): 8.18 (d, 2H), 7.85 ~ 7.79 (m, 3H), 7.72 (s, 1H), 7.51 ~ 7.23 (m, 21H)

MS / FAB: 554 (M ⁺ )

[Synthesis Example 53] Synthesis of compound [53]

5 g (14.66 mmol) of 4- (4,5-diphenyl-4H-1,2,4-triazol-3-yl) phenylboronic acid and 3-chloro-4,5-di in the same manner as in Synthesis example 19 3.7 g (14.66 mmol) of phenyl-4H-1,2,4-triazole were used to obtain 3.9 g (51%) of the target compound [53] as an off-white solid.

¹ H NMR (300 MHz, CDCl ₃ ): 8.18 (d, 4H), 7.75 (s, 4H), 7.48 ~ 7.31 (m, 16H)

MS / FAB: 520 (M ⁺ )

[Synthesis Example 54] Synthesis of compound [54]

In the same manner as in Synthesis example 19, 5 g (13.29 mmol) of 3- (4-bromophenyl) -4,5-diphenyl-4H-1,2,4-triazole, 3.4 g (13.29) of an intermediate [53-1] mmol) gave 3.9 g (50%) of the title compound [54] as an off-white solid.

¹ H NMR (300 MHz, CDCl ₃ ): 8.18 (d, 4H), 7.75 (d, 4H), 7.48-7.31 (m, 16H), 7.15 (d, 4H)

MS / FAB: 593 (M ⁺ )

[Synthesis Example 55] Synthesis of compound [55]

In the same manner as in Synthesis example 19, 5 g (12.38 mmol) of 9,9'-spirobibi [florene] -2,7'-diyl diboronic acid and 3-chloro-4,5-diphenyl-4H-1,2, 6.3 g (24.75 mmol) of 4-triazole were used to obtain 5.4 g (58%) of the target compound [55] as an off-white solid.

¹ H NMR (300 MHz, CDCl ₃ ): 8.18 (d, 4H), 7.77 ~ 7.71 (m, 4H), 7.57 (s, 2H), 7.48 ~ 7.31 (m, 20H), 7.18 ~ 7.12 (m, 4H )

MS / FAB: 755 (M ⁺ )

Comparative Example 1

Using compound a represented by the following formula a as a phosphorescent host, using a compound represented by the following formula b as a phosphorescent dopant, 2-TNATA (4,4 ', 4 "-tris (N-naphthalen-2-yl ) -N-phenylamino) -triphenylamine) is used as the hole injection layer material, and α-NPD (N, N'-di (naphthalene-1-yl) -N, N'-diphenylbenzidine) is used as the hole transport layer material. An organic light emitting device was manufactured having the following structure: ITO / 2-TNATA (80nm) / α-NPD (30nm) / Compound a + Compound b (30nm) / Alq3 (30nm) / LiF (0.5nm) / Al (60 nm).

Anode cuts Corning's 15Ω / cm ² (1000Å) ITO glass substrate into 50mm x 50mm x 0.7mm sizes, ultrasonically cleans for 15 minutes in acetone isopropyl alcohol and pure water, and then UV ozone for 30 minutes. It was used by washing. 2-TANATA was vacuum-deposited on the substrate to form a hole injection layer having a thickness of 80 nm. On top of the hole injection layer,? -NPD was vacuum deposited to form a hole transport layer having a thickness of 30 nm. Compound a represented by Formula a and Compound b represented by Formula b (8% doping) were vacuum deposited on the hole transport layer to form a light emitting layer having a thickness of 30 nm. Then, an Alq3 compound was vacuum deposited on the light emitting layer to a thickness of 30 nm to form an electron transporting layer. LiF 0.5 nm (electron injection layer) and Al 60 nm (cathode) were sequentially vacuum-deposited on the electron transporting layer to form an organic light emitting device as shown in FIG. 1B. This is referred to as Comparative Sample 1.

Comparative Example 2

Using compound a represented by the following formula a as a phosphorescent host, using compound c represented by the following formula c as a phosphorescent dopant, 2-TNATA (4,4 ', 4 "-tris (N-naphthalen-2- yl) -N-phenylamino) -triphenylamine) is used as the hole injection layer material, and α-NPD (N, N'-di (naphthalene-1-yl) -N, N'-diphenylbenzidine) is used as the hole transport layer material. Thus, an organic light emitting device having the following structure was prepared: ITO / 2-TNATA (80 nm) / α-NPD (30 nm) / Compound a + Compound c (30 nm) / Alq 3 (30 nm) / LiF (0.5 nm) / Al (60 nm).

Anode cuts Corning's 15Ω / cm ² (1000Å) ITO glass substrate into 50mm x 50mm x 0.7mm sizes, ultrasonically cleans for 15 minutes in acetone isopropyl alcohol and pure water, and then UV ozone for 30 minutes. It was used by washing. 2-TANATA was vacuum-deposited on the substrate to form a hole injection layer having a thickness of 80 nm. On top of the hole injection layer,? -NPD was vacuum deposited to form a hole transport layer having a thickness of 30 nm. Compound (a) represented by formula (a) and compound c (10% doped) represented by formula (c) were vacuum deposited on the hole transport layer to form a 30 nm thick light emitting layer. Then, an Alq3 compound was vacuum deposited on the light emitting layer to a thickness of 30 nm to form an electron transporting layer. LiF 0.5 nm (electron injection layer) and Al 60 nm (cathode) were sequentially vacuum-deposited on the electron transporting layer to form an organic light emitting device as shown in FIG. 1B. This is referred to as Comparative Sample 2.

Comparative Example 3

Using compound a represented by the following formula a as a phosphorescent host, compound d represented by the following formula d as a phosphorescent dopant, 2-TNATA (4,4 ', 4 "-tris (N-naphthalen-2- yl) -N-phenylamino) -triphenylamine) is used as the hole injection layer material, and α-NPD (N, N'-di (naphthalene-1-yl) -N, N'-diphenylbenzidine) is used as the hole transport layer material. Thus, an organic light emitting device having the following structure was manufactured: ITO / 2-TNATA (80 nm) / α-NPD (30 nm) / Compound a + Compound d (30 nm) / Alq 3 (30 nm) / LiF (0.5 nm) / Al (60 nm).

Anode cuts Corning's 15Ω / cm ² (1000Å) ITO glass substrate into 50mm x 50mm x 0.7mm sizes, ultrasonically cleans for 15 minutes in acetone isopropyl alcohol and pure water, and then UV ozone for 30 minutes. It was used by washing. 2-TANATA was vacuum-deposited on the substrate to form a hole injection layer having a thickness of 80 nm. On top of the hole injection layer,? -NPD was vacuum deposited to form a hole transport layer having a thickness of 30 nm. Compound (a) represented by Formula (a) and compound d (8% doped) represented by Formula (d) were vacuum deposited on the hole transport layer to form a 30 nm thick light emitting layer. Then, an Alq3 compound was vacuum deposited on the light emitting layer to a thickness of 30 nm to form an electron transporting layer. LiF 0.5 nm (electron injection layer) and Al 60 nm (cathode) were sequentially vacuum-deposited on the electron transporting layer to form an organic light emitting device as shown in FIG. 1B. This is referred to as Comparative Sample 3.

In this comparative example and the following comparative examples and embodiments, devices were fabricated by using an EL evaporator manufactured by DeVoiste.

<Formula a> <Formula b>

<Formula c> <Formula d>

Examples 1-24

In Comparative Example 1, except that Compound 1 to 51 represented by Formulas 1 to 51 disclosed in Synthesis Example were used as the emitting layer phosphorescent host compound instead of Compound a as the emitting layer phosphorescent host compound, in the same manner as in Comparative Example 1 Structure of ITO / 2-TNATA (80nm) / α-NPD (30nm) / [one of phosphorescent host compounds 1-51 + compound b] (30nm) / Alq3 (30nm) / LiF (0.5nm) / Al (60nm) An organic light emitting device was manufactured. These are called Samples 1 to 51, respectively.

Evaluation Example 1 Evaluation of Luminescence Characteristics of Comparative Sample 1 and Samples 1 to 51

For Comparative Sample 1 and Samples 1 to 51, light emission luminance, light emission efficiency, and light emission peak were evaluated using Keithley SMU 235 and PR650, and the results are shown in Table 1 below. The samples showed green emission peaks in the range of 516-524 nm.

Sample No. Host
compound
No. Dopant
compound
No. Luminance
[cd / m ² ] efficiency
[cd / A] Luminous Peak
[nm] Comparative Sample 1 a b 2325 23.2 516 One One b 2860 28.6 520 2 2 b 2843 28.4 520 3 3 b 2751 27.5 516 4 4 b 2643 26.4 516 5 5 b 2752 27.5 516 6 6 b 2936 29.4 520 7 7 b 2972 29.7 520 8 8 b 2856 28.6 520 9 9 b 2638 26.4 516 10 10 b 2841 28.4 520 11 11 b 2895 28.9 516 12 12 b 2673 26.7 516 13 13 b 2809 28.1 520 14 14 b 2942 29.4 520 15 15 b 2753 27.5 520 16 16 b 2860 28.6 516 17 17 b 2863 28.6 516 18 18 b 3022 30.2 516 19 19 b 2943 29.4 520 20 20 b 3046 30.5 516 21 21 b 2839 28.4 516 22 22 b 2776 27.8 520 23 23 b 2841 28.4 516 24 24 b 2763 27.6 520 25 25 b 2923 29.2 516 26 26 b 2643 26.4 516 27 27 b 2684 26.8 516 28 28 b 2761 27.6 520 29 29 b 2840 28.4 520 30 30 b 2976 29.7 520 31 31 b 2758 27.6 516 32 32 b 2669 26.7 516 33 33 b 2758 27.6 520 34 34 b 2842 28.4 516 35 35 b 2963 29.6 520 36 36 b 3021 30.2 516 37 37 b 2743 27.4 520 38 38 b 2864 28.6 516 39 39 b 2741 27.4 516 40 40 b 2763 27.6 520 41 41 b 2938 29.4 520 42 42 b 2953 29.5 520 43 43 b 2991 29.9 516 44 44 b 2674 26.7 516 45 45 b 2630 26.3 516 46 46 b 2834 28.3 520 47 47 b 2561 25.6 516 48 48 b 3018 30.2 520 49 49 b 2853 28.5 516 50 50 b 2945 29.4 516 51 51 b 2761 27.6 520

As shown in Table 1, Samples 1 to 51 showed improved luminescence properties compared to Comparative Sample 1.

Example  52-56

In Comparative Example 2, compounds 5, 16, 25, 46, and 50 represented by Formulas 5, 16, 25, 46, and 50 disclosed in Synthesis Example, respectively, were used as light emitting layer phosphorescent host compounds instead of compound a as light emitting layer phosphorescent host compounds. Except that ITO / 2-TNATA (80nm) / α-NPD (30nm) / [phosphorescent host compound 5, 16, 25, 46 and 50 + compound c] (30nm) in the same manner as in Comparative Example 2 An organic light emitting diode having a structure of / Alq 3 (30 nm) / LiF (0.5 nm) / Al (60 nm) was prepared. These are referred to as samples 52 to 56, respectively.

Evaluation example  2: Evaluation of Luminescence Characteristics of Comparative Sample 2 and Samples 52-56

For Comparative Sample 2 and Samples 52 to 56, light emission luminance, light emission efficiency, and light emission peak were evaluated using Keithley SMU 235 and PR650, respectively, and the results are shown in Table 2 below. The samples showed red emission peaks in the range of 610-616 nm.

Sample No. Host
compound
No. Dopant
compound
No. Luminance
[cd / m ² ] efficiency
[cd / A] Luminous Peak
[nm] Comparative Sample 2 a c 795 7.9 616 52 5 c 953 9.5 610 53 16 c 938 9.4 616 54 25 c 872 8.7 610 55 46 c 979 9.8 616 56 50 c 1020 10.2 610

As shown in Table 2, Samples 52 to 56 showed improved luminescence properties compared to Comparative Sample 2.

Examples 57-59

Comparative Example 3 of Comparative Example 3, except that Compound 12, 24, and 38 represented by Chemical Formulas 12, 24, and 38, disclosed in Synthesis Example, were used as the emission layer phosphorescent host compound instead of Compound a, respectively. ITO / 2-TNATA (80nm) / α-NPD (30nm) / [phosphorescent host compound 9, 10 + compound d] (30nm) / Alq3 (30nm) / LiF (0.5nm) / Al ( An organic light emitting device having a structure of 60 nm) was prepared. These are referred to as samples 57 to 59, respectively.

Evaluation example  3: Evaluation of Luminescence Characteristics of Comparative Sample 3 and Samples 57-59

For Comparative Sample 3 and Samples 57 to 59, luminescence brightness, luminescence efficiency, and luminescence peak were evaluated using Keithley SMU 235 and PR650, respectively, and the results are shown in Table 3 below. The samples showed blue emission peak values in the range of 471-475 nm.

Sample No. Host
compound
No. Dopant
compound
No. Luminance
[cd / m ² ] efficiency
[cd / A] Luminous Peak
[nm] Comparative Sample 3 a d 662 6.6 475 57 12 d 937 9.4 475 58 24 d 901 9.0 475 59      38 d 992 9.9 471

As shown in Table 3, Samples 56 to 59 showed improved luminescence properties compared to Comparative Sample 3.

Evaluation Example 4 Evaluation of Life Characteristics of Comparative Sample 1 and Samples 5, 13, 18, 25, 34, and 47

For Comparative Sample 1 and Samples 5, 13, 18, 25, 34 and 47, the intensity of luminescence was reduced to 70% of the initial value based on the luminance 5000 nits in DC mode using the Lifetime Evaluation Equipment (LTS-1004C). Life time was evaluated by time, and the results are shown in Table 4 below.

Sample No. Host
compound
No. Dopant
compound
No. life span
[70%-time] Comparative Sample 1 a b 50 hours 00 minutes 5 4 b 69 hours 31 minutes 13 11 b 62 hours 26 minutes 18 16 b 65 hours 55 minutes 25 17 b 70 hours 08 minutes 34 19 b 69 hours 41 minutes 47 21 b 67 hours 22 minutes

As shown in Table 4, Samples 5, 13, 18, 25, 34, and 47 showed improved life characteristics compared to Comparative Sample 1.

Claims (8)

An organic light emitting compound represented by formula (I)
(I)

In Formula I,
A is CH or N;
B ₁ , B ₂ and B ₃ are each independently a covalent bond, a phenylene group, or a biphenylene group,
R ₁ , R ₂ and R ₃ are independently of each other

,

, Substituted or unsubstituted triazole group, 9,9'-di (C ₁ -C ₅ alkyl) silafluorenyl group, 9,9'-di (C ₆ -C ₂₀ aryl) silafluorenyl group, dibenzothio Phenyl group, triphenylenyl group or phenyl group,
CY1 and CY2 are each independently a substituted or unsubstituted C ₆ -C ₅₀ aromatic ring, or a substituted or unsubstituted C ₂ -C ₅₀ heteroaromatic ring,
CY3 is a substituted or unsubstituted C ₇ -C ₅₀ aromatic ring, or a substituted or unsubstituted C ₂ -C ₅₀ heteroaromatic ring,
Provided that R ₁ , R ₂ and R ₃ are not a phenyl group at the same time. The compound of claim 1, wherein the CY 1 and CY 2 are independently of each other, benzene, N- (C ₆ -C ₂₀ aryl) carbazole, 9,9′-di (C ₁ -C ₅ alkyl) fluorene, dibenzoti Offen, 9,9'-di (C ₁ -C ₅ alkyl) silafluorene, 1,1'-di (C ₁ -C ₅ alkyl) indene, N- (C ₆ -C ₂₀ aryl) indole, indolo An aromatic or heteroaromatic ring derived from a compound selected from the group consisting of carbazole and derivatives thereof,
CY3 is N- (C ₆ -C ₂₀ aryl) carbazole, 9,9'-di (C ₁ -C ₅ alkyl) fluorene, dibenzothiophene, 9,9'-di (C ₁ -C ₅ alkyl Derived from a compound selected from the group consisting of silafluorene, 1,1'-di (C ₁ -C ₅ alkyl) indene, N- (C ₆ -C ₂₀ aryl) indole, indolocarbazole and derivatives thereof An organic light emitting compound, characterized in that an aromatic or heteroaromatic ring. The method of claim 1, wherein the triazole group, the aromatic ring, the substituent of the heteroaromatic ring is independently of each other C ₁ -C ₅₀ alkyl group; C ₆ -C ₅₀ aryl groups unsubstituted or substituted with C ₁ -C ₅₀ alkyl groups; And a C ₂ -C ₅₀ heteroaryl group which is unsubstituted or substituted with a C ₁ -C ₅₀ alkyl group. The organic light emitting compound of claim 1, wherein the compound is represented by the following Chemical Formulas 1 to 25, 28 to 38, 40 to 49, and 51 to 54:
&Lt; Formula 1 >< EMI ID =

<Formula 3><Formula4>

<Formula 5><Formula6>

&Lt; Formula 7 &gt;&lt; EMI ID =

<Formula 9><Formula10>

<Formula 11><Formula12>

<Formula 13><Formula14>

<Formula 15><Formula16>

<Formula 17><Formula18>

<Formula 19><Formula20>

<Formula 21><Formula22>

<Formula 23><Formula24>

<Formula 25>

<Formula 28>

<Formula 29><Formula30>

<Formula 31><Formula32>

<Formula 33><Formula34>

<Formula 35><Formula36>

<Formula 37><Formula38>

<Formula 40>

<Formula 41><Formula42>

<Formula 43><Formula44>

<Formula 45><Formula46>

<Formula 47><Formula48>

<Formula 49>

<Formula 51><Formula52>

<Formula 53><Formula54>

A first electrode; A second electrode; And an organic light emitting device comprising at least one organic film between the first electrode and the second electrode, wherein the organic film comprises a compound according to any one of claims 1 to 4. . The organic light emitting device of claim 5, wherein the organic layer is a light emitting layer, a hole injection layer, or a hole transport layer. The method of claim 6, 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 first electrode and the second electrode. An organic light emitting device characterized in that. The method of claim 7, wherein the device is a first electrode / hole injection layer / light emitting layer / electron transport layer / electron injection layer / second electrode, the first electrode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / electron injection layer / An organic light emitting device having a structure of a second electrode or a first electrode / hole injection layer / hole transport layer / light emitting layer / hole blocking layer / electron transport layer / electron injection layer / second electrode.

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