KR20160074429A - Novel compound and organic electroluminescent device comprising same - Google Patents

Abstract

The present invention relates to a novel compound and, more specifically, to a novel compound having excellent hole and electron transport properties, capable of simultaneously implementing high triplet energy and high Tg, and capable of allowing an organic light emitting device to have low driving voltage, low power consumption, high efficiency and long lifespan when being applied to an organic light emitting device, and to an organic light emitting device comprising the same.

Description

TECHNICAL FIELD [0001] The present invention relates to a novel compound and an organic light emitting device comprising the compound.

The present invention relates to a novel compound and an organic light emitting device including the same. More particularly, the present invention relates to an organic light emitting device having excellent hole and electron transfer characteristics, high triplet energy and high Tg, Low power consumption, high efficiency and long life.

In recent years, an organic light emitting device capable of being driven by a low voltage in a self-luminous mode has a better viewing angle and contrast ratio than a liquid crystal display (LCD), which is a mainstream of a flat panel display device, It has been attracting attention as a next generation display device because it is advantageous in terms of power consumption and has a wide color reproduction range.

A material used as an organic material layer in an organic light emitting device can be classified into a light emitting material, a hole injecting material, a hole transporting material, an electron transporting material, and an electron injecting material depending largely on functions. The light emitting material may be classified into a polymer and a low molecular weight depending on the molecular weight, and may be classified into a fluorescent material derived from singlet excitation state of electrons and a phosphorescent material derived from the triplet excited state of electrons according to an emission mechanism, Can be classified into blue, green and red light emitting materials and yellow and orange light emitting materials necessary for realizing a better natural color depending on the emission color. Further, in order to increase the color purity and to increase the luminous efficiency through energy transfer, a host / dopant system can be used as a luminescent material. The principle is that when a small amount of dopant having a smaller energy band gap and a higher luminous efficiency than a host mainly constituting the light emitting layer is mixed with the light emitting layer in a small amount, the excitons generated in the host are transported to the dopant to emit light with high efficiency. At this time, since the wavelength of the host is shifted to the wavelength of the dopant, the light of the desired wavelength can be obtained according to the type of the dopant and the host.

Various compounds have been known as materials used in such organic light emitting devices. However, organic light emitting devices using known materials have been difficult to put to practical use due to high driving voltage, low efficiency, and short lifetime. Accordingly, efforts have been made to develop an organic light emitting device having low voltage driving, high luminance, and long life using a material having excellent characteristics.

In order to solve the above-mentioned problems, the present invention provides an organic electroluminescent device having excellent hole and electron transfer characteristics, high triplet energy and high Tg, And to provide a novel compound which is capable of producing a compound having an amino acid sequence represented by SEQ ID NO:

The present invention also provides an organic electroluminescent device capable of realizing high triplet energy and high Tg and having high hole and electron transfer characteristics, including the novel compound, at the same time, has low driving voltage, low power consumption, high efficiency and long life And an object thereof is to provide a device.

In order to accomplish the above object, the present invention provides a compound represented by the following formula 1:

[Chemical Formula 1]

In this formula,

A is one of the following formulas (2) or (3), * is a bonding moiety,

(2)

(3)

X is each independently N or CR ^0, R ⁰ are each independently hydrogen; heavy hydrogen; halogen; An amino group; A nitrile group; A nitro group; Alkyl group of deuterium, halogen group, amino group, nitrile group, C _{1 -30,} which is unsubstituted or substituted with nitro; A C ₂ -C ₃₀ alkenyl group which is unsubstituted or substituted with a halogen, an amino group, a nitrile group, or a nitro group; A C ₂ -C ₃₀ alkynyl group which is unsubstituted or substituted with a nitro group, a halogen, an amino group, a nitrile group or a nitro group; A halogen, an amino group, a nitrile group, an alkoxy group of C _{1 - 30} which is unsubstituted or substituted with a nitro group; A C ₆ -C ₃₀ aryloxy group optionally substituted by deuterium, a halogen, an amino group, a nitrile group, a nitro group; A C _{6 -50} aryl group unsubstituted or substituted with a halogen, an amino group, a nitrile group, or a nitro group; Or a deuterium, a halogen, an amino group, a nitrile group, a nitro group a substituted or unsubstituted C _{2 -50} heteroaryl group,

Ar _1, Ar ₂ are each independently a heavy hydrogen, a halogen, an amino group, a nitrile group, a nitro group, an alkoxy group of C _{1 -30,} C _{2 -30} alkenyl, C _{2 -30} alkynyl group, C _{1 -30} of the an aryl group of group, a C _{6 -30} aryloxy group, C _6-30 aryl, or C _{2 -30 -50} C ₆ optionally substituted heteroaryl group of the; Or a deuterium, a halogen, an amino group, a nitrile group, a nitro group, an alkoxy group of C _{1 -30} alkyl, C _{2 -30} alkenyl, C _{2 -30} alkynyl group, C _{1 -30} of the aryl of C _{6 -30} An aryl group having _{6 to 30} carbon atoms or a heteroaryl group having _{2 to 50} carbon atoms which is unsubstituted or substituted with a heteroaryl group having _{2 to 30} carbon _atoms ,

Y is O, S, NAr, where Ar is heavy hydrogen, a halogen, an amino group, a nitrile group, a nitro group, an alkyl group of C _1-30, C _{2 -30} alkenyl, C _{2 -30} of the alkynyl group, C _{1 -} alkoxy group, an aryl group of C _{6 -30} aryloxy group, C _{6 -30} aryl group, or a C ₂ C _{6 -30 -50} group optionally substituted heteroaryl of the _30; Or a deuterium, a halogen, an amino group, a nitrile group, a nitro group, an alkoxy group of C _{1 -30} alkyl, C _{2 -30} alkenyl, C _{2 -30} alkynyl group, C _{1 -30} of the aryl of C _{6 -30} An aryl group having _{6 to 30} carbon atoms or a heteroaryl group having _{2 to 50} carbon atoms which is unsubstituted or substituted with a heteroaryl group having _{2 to 30} carbon _atoms ,

R ₁ to R ₁₂ are each independently hydrogen; heavy hydrogen; halogen; An amino group; A nitrile group; A nitro group; A halogen atom, an amino group, a nitrile group, a C _1-30 alkyl group unsubstituted or substituted with a nitro group; A C ₂ -C ₃₀ alkenyl group which is unsubstituted or substituted with a halogen, an amino group, a nitrile group, or a nitro group; A C ₂ -C ₃₀ alkynyl group which is unsubstituted or substituted with a nitro group, a halogen, an amino group, a nitrile group or a nitro group; A halogen, an amino group, a nitrile group, an alkoxy group of C _{1 - 30} which is unsubstituted or substituted with a nitro group; A C ₆ -C ₃₀ aryloxy group optionally substituted by deuterium, a halogen, an amino group, a nitrile group, a nitro group; A C _{6 -50} aryl group unsubstituted or substituted with a halogen, an amino group, a nitrile group, or a nitro group; Or a deuterium, a halogen, an amino group, a nitrile group, a nitro group a substituted or unsubstituted C _{2 -50} heteroaryl group,

a and b each independently represents an integer of 0 to 3,

m is independently 0 or 1;

Also, the present invention provides an organic light emitting device including the compound represented by Formula 1.

The compound of the present invention can exhibit excellent hole and electron transfer characteristics, high triplet energy and high Tg when applied to an organic light emitting device, and can have low driving voltage, low power consumption, high efficiency and long life.

1 schematically shows a cross section of an OLED according to an embodiment of the present invention.
The sign
10: substrate
11: anode
12: Hole injection layer
13: hole transport layer
14:
15: electron transport layer
16: cathode

The compounds of the present invention are represented by the following formula (1).

[Chemical Formula 1]

In this formula,

A is one of the following formulas (2) or (3), * is a bonding moiety,

(2)

(3)

X is each independently N or CR ^0, R ⁰ are each independently hydrogen; heavy hydrogen; halogen; An amino group; A nitrile group; A nitro group; Alkyl group of deuterium, halogen group, amino group, nitrile group, C _{1 -30,} which is unsubstituted or substituted with nitro; A C ₂ -C ₃₀ alkenyl group which is unsubstituted or substituted with a halogen, an amino group, a nitrile group, or a nitro group; A C ₂ -C ₃₀ alkynyl group which is unsubstituted or substituted with a nitro group, a halogen, an amino group, a nitrile group or a nitro group; A halogen, an amino group, a nitrile group, an alkoxy group of C _{1 - 30} which is unsubstituted or substituted with a nitro group; A C ₆ -C ₃₀ aryloxy group optionally substituted by deuterium, a halogen, an amino group, a nitrile group, a nitro group; A C _{6 -50} aryl group unsubstituted or substituted with a halogen, an amino group, a nitrile group, or a nitro group; Or a deuterium, a halogen, an amino group, a nitrile group, a nitro group a substituted or unsubstituted C _{2 -50} heteroaryl group,

Ar _1, Ar ₂ are each independently a heavy hydrogen, a halogen, an amino group, a nitrile group, a nitro group, an alkoxy group of C _{1 -30,} C _{2 -30} alkenyl, C _{2 -30} alkynyl group, C _{1 -30} of the an aryl group of group, a C _{6 -30} aryloxy group, C _6-30 aryl, or C _{2 -30 -50} C ₆ optionally substituted heteroaryl group of the; Or a deuterium, a halogen, an amino group, a nitrile group, a nitro group, an alkoxy group of C _{1 -30} alkyl, C _{2 -30} alkenyl, C _{2 -30} alkynyl group, C _{1 -30} of the aryl of C _{6 -30} An aryl group having _{6 to 30} carbon atoms or a heteroaryl group having _{2 to 50} carbon atoms which is unsubstituted or substituted with a heteroaryl group having _{2 to 30} carbon _atoms ,

Y is O, S, NAr, where Ar is heavy hydrogen, a halogen, an amino group, a nitrile group, a nitro group, an alkyl group of C _1-30, C _{2 -30} alkenyl, C _{2 -30} of the alkynyl group, C _{1 -} alkoxy group, an aryl group of C _{6 -30} aryloxy group, C _{6 -30} aryl group, or a C ₂ C _{6 -30 -50} group optionally substituted heteroaryl of the _30; Or a deuterium, a halogen, an amino group, a nitrile group, a nitro group, an alkoxy group of C _{1 -30} alkyl, C _{2 -30} alkenyl, C _{2 -30} alkynyl group, C _{1 -30} of the aryl of C _{6 -30} An aryl group having _{6 to 30} carbon atoms or a heteroaryl group having _{2 to 50} carbon atoms which is unsubstituted or substituted with a heteroaryl group having _{2 to 30} carbon _atoms ,

R ₁ to R ₁₂ are each independently hydrogen; heavy hydrogen; halogen; An amino group; A nitrile group; A nitro group; A halogen atom, an amino group, a nitrile group, a C _1-30 alkyl group unsubstituted or substituted with a nitro group; A C ₂ -C ₃₀ alkenyl group which is unsubstituted or substituted with a halogen, an amino group, a nitrile group, or a nitro group; A C ₂ -C ₃₀ alkynyl group which is unsubstituted or substituted with a nitro group, a halogen, an amino group, a nitrile group or a nitro group; A halogen, an amino group, a nitrile group, an alkoxy group of C _{1 - 30} which is unsubstituted or substituted with a nitro group; A C ₆ -C ₃₀ aryloxy group optionally substituted by deuterium, a halogen, an amino group, a nitrile group, a nitro group; A C _{6 -50} aryl group unsubstituted or substituted with a halogen, an amino group, a nitrile group, or a nitro group; Or a deuterium, a halogen, an amino group, a nitrile group, a nitro group a substituted or unsubstituted C _{2 -50} heteroaryl group,

a and b each independently represents an integer of 0 to 3,

m is independently 0 or 1;

Specifically, the compound of formula (1) may be one of the following formulas (1-1) to (1-4).

[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

X, Ar ₁ , Ar ₂ , R ₁ to R ₁₁ , a and b in the general formulas 1-1 to 1-4 are as defined in the general formula (1).

In this case, the driving voltage and efficiency can be further improved.

In the present invention, specific examples of the compound represented by the formula (1) are as follows:

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The compound of formula (1) according to the present invention has excellent hole and electron transfer characteristics, can realize high triplet energy and high Tg, has low driving voltage, low power consumption, high efficiency and long life, And excellent device characteristics can be exhibited.

The compounds of the present invention may also be prepared through the reaction schemes represented by the following Reaction Schemes 1 or 2:

[Reaction Scheme 1]

[Reaction Scheme 2]

In the above Reaction Schemes 1 and 2, A, X, Ar ₁ , Ar ₂ , R ₁ to R ₄ , a and b are as defined in Formula (1).

Also, the present invention provides an organic light emitting device comprising a compound represented by Formula 1 in an organic material layer. Specifically, the organic light emitting device according to the present invention includes the compound represented by Formula 1 as a light emitting material, At this time, the compound of the present invention may be used alone or in combination with a known organic light emitting compound. In the organic light emitting device of the present invention, the compound represented by Formula 1 may be used as an electron transporting material in an electron transporting layer, or as a hole blocking material in a hole blocking layer. At this time, the electron transporting layer or the hole blocking layer may be formed of a known material in addition to the compound represented by the above formula (1).

In addition, the organic light emitting device of the present invention includes one or more organic layers including the compound represented by Formula 1, and the method of manufacturing the organic light emitting device will now be described.

The organic light emitting device includes a hole injection layer 12, a hole transport layer 13, an HTL, a light emitting layer 14, an EML, an electron transport layer 15, and an electron transport layer 15 between the anode 11 and the cathode 16. [ ), An electron injection layer (EIL), and the like.

First, an anode electrode material having a high work function is deposited on the substrate 10 to form an anode 11. At this time, the substrate 10 may be a substrate used in a conventional organic light emitting device. In particular, a glass substrate or a transparent plastic substrate having excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, It is good. As the material for the anode electrode, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO ₂ ), zinc oxide (ZnO) and the like which are transparent and excellent in conductivity can be used. The anode electrode material can be deposited by a conventional anode formation method, and specifically, it can be deposited by a deposition method or a sputtering method.

Next, a hole injection layer 12 may be formed on the anode (11) electrode. The hole injection layer 12 may be formed by a vacuum deposition method, a spin coating method, a casting method, a Langmuir-Blodgett (LB) method, or the like.

The hole injection layer material is not particularly limited and may be a phthalocyanine compound such as copper phthalocyanine disclosed in U.S. Patent No. 4,356,429 or a star burst type amine derivative TCTA (4,4 ', 4 "-tri (N-carbazolyl) tri (4,4 ', 4 "-tris (3-methylphenylamino) triphenylamine), m-MTDAPB ^{), HI-406 (N 1} , N 1 '- ( biphenyl-4,4'-diyl) bis (N ¹ - (naphthalen-1-yl) -N ^4, N ⁴ - benzene-1,4-diphenyl -Diamine) can be used as a hole injection layer material.

Next, a hole transport layer 13 may be formed on the hole injection layer 12. The hole transport layer 13 may be formed by a method such as a vacuum deposition method, a spin coating method, a casting method, an LB method, or the like.

The hole transport layer material is not particularly limited and may be selected arbitrarily from commonly known materials used in the hole transport layer. Specifically, the hole transport layer material may be a carbazole derivative such as N-phenylcarbazole or polyvinylcarbazole, a carbazole derivative such as N, N'-bis (3-methylphenyl) -N, N'- Phenyl) -4,4'-diamine (TPD), and N, N'-di (naphthalene-1-yl) -N, N'-diphenylbenzidine Derivatives and the like can be used.

Thereafter, one or more organic layers may be further formed between the hole transport layer 13 and the light emitting layer 14 described later. Specifically, the organic layer may be an emission assist layer, and the emission auxiliary layer may be formed on the hole transport layer. The organic layer (for example, the light emitting auxiliary layer) can be formed by a method such as a vacuum deposition method, a spin coating method, a casting method, an LB method, or the like. The organic layer (for example, the light-emitting auxiliary layer) may be a known organic layer material.

Thereafter, the light emitting layer 14 may be formed on the hole transport layer 13 or the light emitting auxiliary layer. The light emitting layer 14 can be formed by a method such as a vacuum deposition method, a spin coating method, a casting method, an LB method, or the like. The light emitting layer material may use a compound represented by the formula (1) of the present invention as a host or a dopant.

When the compound represented by Formula 1 is used as a light emitting host, a phosphorescent or fluorescent dopant may be used together to form a light emitting layer. At this time, the fluorescent dopant to the possible purchase from Idemitsu Co. (Idemitsu Corporation) IDE102 or IDE105, or BD142 (N ^6, N ^12-bis (3,4-dimethylphenyl) -N ^6, N ¹² - D-mesityl chrysene - 6,12- diamine) can be used to, as a phosphorescent dopant is a green phosphorescent dopant Ir (ppy) ₃ (tris (2-phenylpyridine) iridium), a blue phosphorescent dopant F ₂ Irpic (iridium (ⅲ) bis [4, (6-difluorophenyl) -pyridinate-N, C2 '] picolinate), UDC's red phosphorescent dopant RD61, etc. can be vacuum vacuum deposited (doped). The doping concentration of the dopant is not particularly limited, but it is preferable that the dopant is doped in an amount of 0.01 to 15 parts by weight relative to 100 parts by weight of the host. If the content of the dopant is less than 0.01 part by weight, the amount of the dopant is not sufficient and coloring is not properly performed. If the amount of the dopant is more than 15 parts by weight, the efficiency may be drastically reduced due to the concentration quenching phenomenon.

When the phosphorescent dopant is used together with the phosphorescent dopant, the hole blocking material (HBL) may be further laminated by a vacuum evaporation method or a spin coating method to prevent the triplet excitons or holes from diffusing into the electron transporting layer. The hole blocking material usable herein may be a compound represented by the formula (1), a known hole blocking material, or a mixture thereof. Examples of known hole blocking materials include oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, and hole blocking materials described in Japanese Patent Application Laid-Open No. 11-329734 (A1). Typically, Phenanthrolines based compounds such as Balq (bis (8-hydroxy-2-methylquinolinonato) -aluminum biphenoxide) (such as UDC company BCP (bassocouroin)) and the like .

The electron transport layer 15 may be formed by a vacuum deposition method, a spin coating method, a casting method, or the like using an electron transporting layer material .

The electron transport layer material serves to stably transport electrons injected from the electron injection electrode, and the kind thereof is not particularly limited. For example, a compound represented by the formula (1), a quinoline derivative, especially tris (8- granola Sat) aluminum (Alq _3), ET4, or (6,6 '- (di-3,4- mesityl-1,1-dimethyl -1H- silol-2,5-diyl) di-2,2'- Pyridine) can be used.

In addition, and electron transport layer 15, materials of the electron injection layer (EIL) and a function to facilitate the electron injection from the cathode to the upper portion can be stacked, an electron injection layer materials include LiF, NaCl, CsF, Li ₂ O , BaO, and the like can be used.

The deposition conditions of the electron transporting layer depend on the compound used, but it is generally preferable to select the conditions within the same range as the formation of the hole injection layer.

Thereafter, an electron injection layer material may be formed on the electron transport layer, and the electron injection layer material may be formed by a vacuum deposition method, a spin coating method, a casting method, or the like.

Finally, a metal for forming a cathode is formed on the electron transport layer 15 or the electron injection layer by a vacuum deposition method, a sputtering method, or the like, and used as a cathode. As the metal for cathode formation, a metal, an alloy, an electrically conductive compound having a low work function, and a mixture thereof can be used. Specific examples thereof include Li, Mg, Al, Al-Li, Ca, Mg-In, Mg-Ag, . Also, a transmissive cathode using ITO or IZO may be used to obtain a front light emitting element.

The organic luminescent device of the present invention is an organic luminescent device having an anode 11, a hole injecting layer 12, a hole transporting layer 13, a light emitting layer 14, an electron transporting layer 15, an electron injecting layer and a cathode 16 Alternatively, a structure of an organic light emitting device having various structures is possible, and it is also possible to form one or two intermediate layers as required.

As described above, the thickness of each organic material layer formed according to the present invention can be controlled depending on the required degree, specifically 10 to 1,000 nm.

In addition, since the organic material layer containing the compound represented by the formula (1) can control the thickness of the organic material layer in the molecular unit, the present invention has advantages of uniform surface and excellent shape stability.

The organic electroluminescent device of the present invention includes the compound represented by the formula (1), and can exhibit high hole and electron transfer characteristics, high triplet energy and high Tg, low driving voltage, low power consumption, high efficiency and long life I have.

Hereinafter, the present invention will be described in detail with reference to the following examples. However, the scope of the present invention is not limited to the following examples.

Synthesis of A1

[Synthesis of A1-1]

To a round bottom flask dibenzo [b, d] furan- 4-ylboronic acid 102.2 g, 1-iodo-2-nitrobenzene 100 g was dissolved in toluene, _{1500 ml K 2 CO 3 (2M} ) 600 ml , and Pd (PPh _{3) 4} 13.9 g, and the mixture was stirred under reflux. After confirming the reaction by TLC, water was added and the reaction was terminated. The organic layer was extracted with EA, filtered under reduced pressure and purified by column to obtain 98.7 g (yield: 85%) of Intermediate A1-1.

[Synthesis of A1]

98 g of the above A1-1 was dissolved in 500 ml of 1,2-dichlorobenzene, 330 ml of P (OEt) ₃ was added, and the mixture was stirred under reflux. The organic layer was extracted with MC, filtered under reduced pressure, and then subjected to column purification to obtain 52.3 g (yield: 60%) of Intermediate A1.

Synthesis of A2

[Synthesis of A2-1]

To a round bottom flask dibenzo [b, d] thiophen- 4-ylboronic acid 109.9 g, 1-iodo-2-nitrobenzene 100 g was dissolved in toluene, _{1500 ml K 2 CO 3 (2M} ) 600 ml , and Pd (PPh _{3) 4} 13.9 g, and the mixture was stirred under reflux. After confirming the reaction by TLC, water was added and the reaction was terminated. The organic layer was extracted with EA, filtered under reduced pressure and purified by column to obtain 99.3 g (81% yield) of intermediate A2-1.

[Synthesis of A2]

99 g of the above A2-1 was dissolved in 490 ml of 1,2-dichlorobenzene, 320 ml of P (OEt) ₃ was added, and the mixture was stirred under reflux. The organic layer was extracted with MC, filtered under reduced pressure, and then subjected to column purification to obtain 54.0 g (yield: 61%) of intermediate A2.

Synthesis of A3

[Synthesis of A3-1 and A3]

124.53 g of 9-phenyl-9H-carbazol-1-yl) boronic acid and 90 g of 1-iodo-2-nitrobenzene were dissolved in 1500 ml of toluene, to which 540 ml of K ₂ CO ₃ (2M) ₃ ) ₄ 12.5 g were added and the mixture was stirred under reflux. After confirming the reaction by TLC, water was added and the reaction was terminated. The organic layer was extracted with EA, filtered under reduced pressure, and then subjected to column purification to obtain intermediate A3-1. A3 was prepared in a manner equivalent to the preparation of A2.

IM1 Synthesis of

In a round bottom flask, 4.41 g of NaH and 30 g of 3-bromo-1H-indole were dissolved in 350 ml of THF and stirred. Triisopropylsilyl chloride (32.45 g) was added to the solution, stirred for 2 hours, and the solvent was filtered under reduced pressure to obtain 50.15 g (yield: 93%) of intermediate IM1-1.

5.2 g of 9H-carbazole, 4.1 g of t-BuONa, 1.05 g of Pd ₂ (dba) _{3 and} 1.3 ml of (t-Bu) ₃ P were dissolved in 150 ml of toluene and refluxed with stirring. After the completion of the reaction was confirmed by TLC, the organic layer was extracted with MC, filtered under reduced pressure, and then subjected to column purification to obtain 8.09 g (yield: 65%) of intermediate IM1-2.

8.0 g of Intermediate IM1-2 and 0.72 g of Tetra-n-butylammonium fluoride were dissolved in 160 ml of THF. After stirring for 1 hour, the organic layer was extracted with distilled water and MC, and filtered to obtain 4.53 g (yield: 88% ).

m / z: 282.12 (100.0%), 283.12 (21.8%), 284.12 (2.4%)

IM2 Synthesis of

Prepared by methods such as IM1-1 round bottom flask IM2-1 10 g, (3- (9H -carbazol-9-yl) phenyl) boronic acid 8.9 g 1,4-dioxan was dissolved in 100 ml K ₂ CO ₃ (2M) was stirred under reflux and then insert the (PPh _{3) 4} 1.0 g 40 ml and Pd. After confirming the reaction by TLC, water was added and the reaction was terminated. The organic layer was extracted with MC, filtered under reduced pressure, purified by column, and recrystallized to obtain 8.33 g (yield: 53%) of IM2-2.

8.3 g of the intermediate IM2-2 and 0.63 g of Tetra-n-butylammonium fluoride were dissolved in 170 ml of THF. After stirring for 1 hour, the organic layer was extracted with distilled water and MC. The filtrate was filtered to obtain 5.2 g (yield: 90% ).

m / z: 358.15 (100.0%), 359.15 (28.3%), 360.15 (4.0%

IM3 Synthesis of

IM3 was synthesized in the same manner as IM1 using 2-bromo-1H-indole as a starting material instead of 3-bromo-1H-indole.

m / z: 282.12 (100.0%), 283.12 (21.8%), 284.12 (2.4%)

IM4 Synthesis of

IM4 was synthesized in the same manner as IM2 using 2-bromo-1H-indole as a starting material instead of 3-bromo-1H-indole.

m / z: 358.15 (100.0%), 359.15 (28.3%), 360.15 (4.0%

IM5 Synthesis of

IM5 was synthesized in the same manner as IM1 using 2-bromo-1H-indole and 9,9-dimethyl-9,10-dihydroacridine instead of 3-bromo-1H-indole and 9H-carbazole.

m / z: 324.16 (100.0%), 325.17 (25.1%), 326.17 (3.0%)

IM6 Synthesis of

IM6 was synthesized in the same manner as IM1 using Intermediate A1 instead of 9H-carbazole.

m / z: 372.13 (100.0%), 373.13 (28.3%), 374.13 (4.2%)

IM7 Synthesis of

IM7 was synthesized in the same manner as IM1 using Intermediate A2 instead of 9H-carbazole.

m / z: 388.10 (100.0%), 389.11 (28.3%), 390.10 (4.7%), 390.11 (4.1%), 389.10

IM8 Synthesis of

IM8 was synthesized in the same manner as IM1 using intermediate A3 instead of 9H-carbazole.

m / z: 447.17 (100.0%), 448.18 (34.9%), 449.18 (5.9%), 448.17

IM9 Synthesis of

Bromo-1H-indole and (4- (9H-carbazol-9-yl) phenyl) boronic acid instead of 3-bromo- IM10 was synthesized in the same manner as IM2.

m / z: 358.15 (100.0%), 359.15 (28.3%), 360.15 (4.0%

IM10 Synthesis of

Indole and (3 '- (9H-carbazol-9-yl) - [1, 3 -bromo-lH- 1'-biphenyl] -3-yl) boronic acid, IM10 was synthesized in the same manner as IM2.

m / z: 434.18 (100.0%), 435.18 (35.6%), 436.19 (5.9%)

Example  1: Synthesis of compound 1

2.5 g of Intermediate IM-1 and 0.26 g of NaH were added to 25 ml of DMF and stirred. 2.83 g of 2-chloro-4,6-diphenylpyrimidine was dissolved in 30 ml of DMF and then slowly added dropwise. After stirring at room temperature, the reaction was terminated by TLC, followed by silica filtration and recrystallization to obtain 2.22 g (yield 49%) of Compound 1.

m / z: 512.20 (100.0%), 513.20 (40.4%), 514.21 (7.5%)

Example  2: Synthesis of Compound 2

Compound 2 was synthesized by the same method as Compound 1 using 4-chloro-2,6-diphenylpyrimidine instead of 2-chloro-4,6-diphenylpyrimidine.

m / z: 512.20 (100.0%), 513.20 (40.4%), 514.21 (7.5%)

Example  3: Synthesis of Compound 3

Compound 3 was synthesized in the same manner as Compound 1 using 2-chloro-4,6-diphenyl-1,3,5-triazine instead of 2-chloro-4,6-diphenylpyrimidine.

m / z: 513.20 (100.0%), 514.20 (38.1%), 515.20 (7.8%), 514.19

Example  4: Synthesis of compound 4

Intermediate IM1 2.0 g, 2- (3- bromophenyl) -4,6-diphenylpyrimidine 3.3 g, t-BuONa 1.0 g, Pd 2 (dba) 3 0.26 g, (t-Bu) ₃ Toluene 30 ml to 0.4 ml P And the mixture was stirred under reflux. After completion of the reaction was confirmed by TLC, the organic layer was extracted with MC, filtered under reduced pressure, and then subjected to column purification to obtain 2.04 g (yield 49%) of Compound 4.

m / z: 588.23 (100.0%), 589.23 (46.9%), 590.24 (10.2%), 591.24

Example  5: Synthesis of Compound 5

Compound 5 was synthesized by the same method as Compound 4 using 4- (3-bromophenyl) -2,6-diphenylpyrimidine instead of 2- (3-bromophenyl) -4,6-diphenylpyrimidine.

m / z: 588.23 (100.0%), 589.23 (46.9%), 590.24 (10.2%), 591.24

Example  6: Synthesis of Compound 6

Compound 6 was synthesized in the same manner as Compound 4 by using 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine instead of 2- (3-bromophenyl) -4,6-diphenylpyrimidine.

m / z: 588.23 (100.0%), 590.23 (44.7%), 591.23 (10.4%), 590.22 (1.8%), 592.24

Example  7: Synthesis of Compound 7

Compound 7 was synthesized in the same manner as Compound 1 using IM2 instead of IM1.

m / z: 588.23 (100.0%), 589.23 (46.9%), 590.24 (10.2%), 591.24

Example  8: Synthesis of Compound 8

Compound 8 was synthesized in the same manner as Compound 2 using IM2 instead of IM1.

m / z: 588.23 (100.0%), 589.23 (46.9%), 590.24 (10.2%), 591.24

Example  9: Synthesis of Compound 9

Compound 9 was synthesized in the same manner as Compound 3 using IM2 instead of IM1.

m / z: 588.23 (100.0%), 590.23 (44.7%), 591.23 (10.4%), 590.22 (1.8%), 592.24

Example  10: Synthesis of Compound 10

Compound 10 was synthesized in the same manner as Compound 1 using IM6 instead of IM1.

m / z: 602.21 (100.0%), 603.21 (46.9%), 604.22 (10.2%), 605.22

Synthesis of Compound 11

Compound 11 was synthesized in the same manner as Compound 2 using IM6 instead of IM1.

m / z: 602.21 (100.0%), 603.21 (46.9%), 604.22 (10.2%), 605.22

Synthesis of Compound 12

Compound 12 was synthesized in the same manner as Compound 3 using IM6 instead of IM1.

m / z: 603.21 (100.0%), 604.21 (44.7%), 605.21 (10.6%), 604.20 (1.8%), 606.22

Example  13: Synthesis of compound 13

Compound 13 was synthesized in the same manner as Compound 3 using IM7 instead of IM1.

m / z: 619.18 (100.0%), 620.19 (44.6%), 621.19 (10.1%), 621.18 (5.4%), 620.18 (2.6%), 622.18

Example  14: Synthesis of compound 14

Compound 14 was synthesized in the same manner as Compound 3 using IM8 instead of IM1.

m / z 678.25 (100.0%) 679.26 51.2% 680.26 12.8% 681.26 2.3% 679.25 2.2% 680.25 1.1%

Example  15: Synthesis of compound 15

Compound 15 was synthesized in the same manner as Compound 3 using IM3 instead of IM1.

m / z: 513.20 (100.0%), 514.20 (38.1%), 515.20 (7.8%), 514.19

Example  16: Synthesis of Compound 16

Compound 16 was synthesized in the same manner as Compound 3 using IM4 instead of IM1.

m / z: 589.23 (100.0%), 590.23 (44.7%), 591.23 (10.4%), 590.22 (1.8%), 592.24

Example  17: Synthesis of Compound 17

Compound 17 was synthesized in the same manner as Compound 3 using IM5 instead of IM1.

m / z: 555.24 (100.0%), 556.25 (41.4%), 557.25 (8.4%), 556.24 (1.8%

Example  18: Synthesis of compound 18

Compound 18 was synthesized in the same manner as Compound 4 using IM3 instead of IM1.

m / z: 589.23 (100.0%), 590.23 (44.7%), 591.23 (10.4%), 590.22 (1.8%), 592.24

Example  19: Synthesis of Compound 19

IM1 and IM3 and 2- (3'-bromo- [1,1'-biphenyl] -3-yl) -4,6-diphenyl- Compound 19 was synthesized in the same manner as Compound 4 using 5-triazine.

m / z: 665.26 (100.0%), 666.26 (51.2%), 667.26 (13.6%), 668.27 (2.1%

Example  20: Synthesis of Compound 20

Compound 20 was synthesized in the same manner as Compound 1 using IM9 instead of IM1.

m / z: 588.23 (100.0%), 589.23 (46.9%), 590.24 (10.2%), 591.24

Example  21: Synthesis of Compound 21

Compound 21 was synthesized in the same manner as Compound 1 using IM9 and 2-chloro-4,6-diphenyl-1,3,5-triazine instead of IM1 and 2-chloro-4,6-diphenylpyrimidine.

m / z: 589.23 (100.0%), 590.23 (44.7%), 591.23 (10.4%), 590.22 (1.8%), 592.24

Example  22: Synthesis of Compound 22

Compound 22 was synthesized in the same manner as Compound 1 using IM10 instead of IM1.

m / z: 664.26 (100.0%), 665.27 (52.3%), 666.27 (13.4%), 667.27 (2.4%), 665.26

Example  23: Synthesis of Compound 23

Compound 23 was synthesized in the same manner as Compound 1 using IM10 and 4-chloro-2,6-diphenylpyrimidine instead of IM1 and 2-chloro-4,6-diphenylpyrimidine.

m / z: 664.26 (100.0%), 665.27 (52.3%), 666.27 (13.4%), 667.27 (2.4%), 665.26

Example  24: Synthesis of Compound 24

Compound 24 was synthesized in the same manner as Compound 1 using IM10 and 2-chloro-4,6-diphenyl-1,3,5-triazine instead of IM1 and 2-chloro-4,6-diphenylpyrimidine.

m / z: 665.26 (100.0%), 666.26 (51.2%), 667.26 (13.6%), 668.27 (2.1%

Example  25: Synthesis of Compound 25

Compound 25 was synthesized in the same manner as Compound 4 using IM9 instead of IM1.

m / z: 664.26 (100.0%), 665.27 (52.3%), 666.27 (13.4%), 667.27 (2.4%), 665.26

Example  26: Synthesis of Compound 26

Compound 26 was synthesized in the same manner as Compound 4 using IM9 and 4- (3-bromophenyl) -2,6-diphenylpyrimidine instead of IM1 and 2- (3-bromophenyl) -4,6-diphenylpyrimidine.

m / z: 664.26 (100.0%), 665.27 (52.3%), 666.27 (13.4%), 667.27 (2.4%), 665.26

Example  27: Synthesis of Compound 27

IM9 and 2- (3-bromophenyl) -4,6-diphenylpyrimidine instead of IM9 and 2- (3-bromophenyl) -4,6-diphenyl-1,3,5- Were synthesized.

m / z: 665.26 (100.0%), 666.26 (51.2%), 667.26 (13.6%), 668.27 (2.1%

Example  28: Synthesis of Compound 28

Compound 28 was synthesized in the same manner as Compound 4 using IM4 instead of IM1.

m / z: 664.26 (100.0%), 665.27 (52.3%), 666.27 (13.4%), 667.27 (2.4%), 665.26

Example  29: Synthesis of Compound 29

Compound 29 was synthesized in the same manner as Compound 4 using IM4 and 4- (3-bromophenyl) -2,6-diphenylpyrimidine instead of IM1 and 2- (3-bromophenyl) -4,6-diphenylpyrimidine.

m / z: 664.26 (100.0%), 665.27 (52.3%), 666.27 (13.4%), 667.27 (2.4%), 665.26

Example  30: Synthesis of compound 30

IM1 and 2- (3-bromophenyl) -4,6-diphenylpyrimidine instead of IM4 and 2- (3-bromophenyl) -4,6-diphenyl-1,3,5- Were synthesized.

m / z: 665.26 (100.0%), 666.26 (51.2%), 667.26 (13.6%), 668.27 (2.1%

Manufacture of organic light emitting device

An organic light emitting device was prepared according to the structure shown in FIG. The organic light emitting device is composed of an anode (hole injecting electrode 11) / hole injecting layer 12 / hole transporting layer 13 / light emitting layer 14 / electron transporting layer 15 / cathode (electron injecting electrode 16) .

The following materials were used for the hole injecting layer 12, the hole transporting layer 13, the light emitting layer 14, and the electron transporting layer 15 of Examples and Comparative Examples.

Example  31

The glass substrate coated with thin film of indium tin oxide (ITO) 1500 Å in thickness was washed with distilled water ultrasonic waves. After the distilled water was cleaned, the substrate was ultrasonically cleaned with a solvent such as isopropyl alcohol, acetone, or methanol, dried, and transferred to a plasma cleaner. Then, the substrate was cleaned using oxygen plasma for 5 minutes, and then a thermal vacuum evaporator evaporator) to form a hole injection layer HI01 600 Å and a hole transport layer NPB 250 Å. Next, the light emitting layer was doped with 10% Ir (ppy) ₃ as a compound 1 to form a 250 Å film. Next, an ET01: Liq (1: 1) 300 Å film was formed as an electron transport layer, LiF 10 Å and aluminum (Al) 1000 Å were formed, and the device was encapsulated in a glove box to produce a green organic light emitting device.

Example  32 - Example  60

Organic light emitting devices were fabricated in the same manner as in Example 1 by using Compound 2 to 30 as a light emitting layer host respectively.

Comparative Example  One

A green organic light emitting device was fabricated in the same manner as in Example 1 except that CBP was used instead of Compound 1 as the light emitting layer host.

Comparative Example  2

A green organic light emitting device was fabricated in the same manner as in Example 1 except that Compound 1 was used as a light emitting layer host instead of Compound 1 (Ref.1).

Comparative Example  3

A green organic light emitting device was fabricated in the same manner as in Example 1 except that Compound 1 was used as a light emitting layer host and Comparative Compound 2 (Ref.2) was used.

Comparative Example  4

A green organic light emitting device was fabricated in the same manner as in Example 1 except that Compound 1 was substituted for Compound 3 (Ref.3) as the light emitting layer host.

Evaluation of performance of organic light emitting device

A voltage was applied to the Keithley 2400 source measurement unit to inject electrons and holes and the luminance was measured using a Konica Minolta spectroscope (CS-2000). The performance of the organic light emitting devices of the examples and comparative examples was evaluated by measuring the current density and the luminance with respect to the applied voltage under the atmospheric pressure condition, and the results are shown in Table 1.

Op. V QE (%) Cd / A lm / w CIEx CIEy life span@
1000nit Example 31 5.08 15.51 43.68 36.31 0.301 0.621 48 Example 32 5.07 15.62 43.21 36.03 0.299 0.619 49 Example 33 5.10 15.49 43.88 36.22 0.298 0.620 50 Example 34 5.04 15.73 44.81 38.51 0.305 0.623 53 Example 35 5.05 15.19 44.21 36.99 0.302 0.614 54 Example 36 5.04 15.80 44.92 38.24 0.300 0.609 50 Example 37 5.09 15.01 44.01 38.12 0.300 0.618 54 Example 38 5.09 15.25 44.65 38.01 0.302 0.609 55 Example 39 5.10 15.90 44.28 38.12 0.305 0.620 54 Example 40 5.05 15.42 44.25 39.91 0.310 0.622 58 Example 41 5.06 15.16 44.11 38.00 0.310 0.624 55 Example 42 5.05 15.99 44.52 37.91 0.308 0.627 54 Example 43 5.06 15.55 44.01 38.22 0.304 0.624 57 Example 44 5.05 15.21 44.65 37.01 0.302 0.622 54 Example 45 5.01 15.23 49.28 42.00 0.300 0.625 65 Example 46 5.01 15.00 49.25 42.78 0.301 0.622 64 Example 47 5.03 15.97 49.11 42.14 0.303 0.623 69 Example 48 5.00 17.31 50.02 42.50 0.302 0.620 72 Example 49 5.00 16.99 50.12 43.00 0.302 0.621 70 Example 50 5.00 17.00 50.21 42.27 0.304 0.621 70 Example 51 5.00 17.13 49.31 43.01 0.300 0.620 70 Example 52 5.03 17.22 51.00 42.51 0.300 0.617 75 Example 53 5.02 17.18 52.53 42.30 0.301 0.615 71 Example 54 5.00 17.15 50.87 43.51 0.304 0.610 83 Example 55 5.01 17.02 50.10 42.98 3.301 0.620 74 Example 56 5.02 16.94 51.31 43.04 0.301 0.615 77 Example 57 5.01 17.00 51.00 43.01 0.304 0.611 80 Example 58 5.03 17.31 52.67 42.91 0.305 0.614 75 Example 59 5.00 17.14 50.55 42.01 0.300 0.619 77 Example 60 5.00 17.05 51.00 43.00 0.302 0.622 75 Comparative Example 1 5.82 8.43 25.12 9.72 0.311 0.630 9 Comparative Example 2 5.91 8.51 24.01 9.83 0.311 0.629 11 Comparative Example 3 5.30 12.10 35.01 27.95 0.305 0.625 30 Comparative Example 4 5.17 13.81 39.50 32.50 0.301 0.621 38

As shown in Table 1, it can be seen that the embodiments of the present invention are superior to the organic EL devices of Comparative Examples 1 to 4 in physical properties. Compared with Comparative Examples 1 and 2, the driving voltage and efficiency were considerably improved in the case of having a heteroaromatic structure in which electron injection was easy, and in comparison with Comparative Example 3 and Comparative Example 4, a fusion ring of carbazole and indole The efficiency and life span of the indole phenylcarbazole substitution were significantly improved. Comparing the Examples also showed that the efficiency and lifetime were further improved in Examples 45 to 60 because the triple energy of the indole 2-substituted compound was higher than that of the indole 3 position so that triphasic energy transfer from the host to the phosphorescent dopant was efficiently You can see what happened.

Claims (6)

A compound represented by the following formula (1):
[Chemical Formula 1]

In this formula,
A is one of the following formulas (2) or (3), * is a bonding moiety,
(2)

(3)

X is each independently N or CR ^0, R ⁰ are each independently hydrogen; heavy hydrogen; halogen; An amino group; A nitrile group; A nitro group; Alkyl group of deuterium, halogen group, amino group, nitrile group, C _{1 -30,} which is unsubstituted or substituted with nitro; A C ₂ -C ₃₀ alkenyl group which is unsubstituted or substituted with a halogen, an amino group, a nitrile group, or a nitro group; A C ₂ -C ₃₀ alkynyl group which is unsubstituted or substituted with a nitro group, a halogen, an amino group, a nitrile group or a nitro group; A halogen, an amino group, a nitrile group, an alkoxy group of C _{1 - 30} which is unsubstituted or substituted with a nitro group; A C ₆ -C ₃₀ aryloxy group optionally substituted by deuterium, a halogen, an amino group, a nitrile group, a nitro group; A C _{6 -50} aryl group unsubstituted or substituted with a halogen, an amino group, a nitrile group, or a nitro group; Or a deuterium, a halogen, an amino group, a nitrile group, a nitro group a substituted or unsubstituted C _{2 -50} heteroaryl group,
Ar _1, Ar ₂ are each independently a heavy hydrogen, a halogen, an amino group, a nitrile group, a nitro group, an alkoxy group of C _{1 -30,} C _{2 -30} alkenyl, C _{2 -30} alkynyl group, C _{1 -30} of the an aryl group of group, a C _{6 -30} aryloxy group, C _6-30 aryl, or C _{2 -30 -50} C ₆ optionally substituted heteroaryl group of the; Or a deuterium, a halogen, an amino group, a nitrile group, a nitro group, an alkoxy group of C _{1 -30} alkyl, C _{2 -30} alkenyl, C _{2 -30} alkynyl group, C _{1 -30} of the aryl of C _{6 -30} An aryl group having _{6 to 30} carbon atoms or a heteroaryl group having _{2 to 50} carbon atoms which is unsubstituted or substituted with a heteroaryl group having _{2 to 30} carbon _atoms ,
Y is O, S, NAr, where Ar is heavy hydrogen, a halogen, an amino group, a nitrile group, a nitro group, an alkyl group of C _1-30, C _{2 -30} alkenyl, C _{2 -30} of the alkynyl group, C _{1 -} alkoxy group, an aryl group of C _{6 -30} aryloxy group, C _{6 -30} aryl group, or a C ₂ C _{6 -30 -50} group optionally substituted heteroaryl of the _30; Or a deuterium, a halogen, an amino group, a nitrile group, a nitro group, an alkoxy group of C _{1 -30} alkyl, C _{2 -30} alkenyl, C _{2 -30} alkynyl group, C _{1 -30} of the aryl of C _{6 -30} An aryl group having _{6 to 30} carbon atoms or a heteroaryl group having _{2 to 50} carbon atoms which is unsubstituted or substituted with a heteroaryl group having _{2 to 30} carbon _atoms ,
R ₁ to R ₁₂ are each independently hydrogen; heavy hydrogen; halogen; An amino group; A nitrile group; A nitro group; A halogen atom, an amino group, a nitrile group, a C _1-30 alkyl group unsubstituted or substituted with a nitro group; A C ₂ -C ₃₀ alkenyl group which is unsubstituted or substituted with a halogen, an amino group, a nitrile group, or a nitro group; A C ₂ -C ₃₀ alkynyl group which is unsubstituted or substituted with a nitro group, a halogen, an amino group, a nitrile group or a nitro group; A halogen, an amino group, a nitrile group, an alkoxy group of C _{1 - 30} which is unsubstituted or substituted with a nitro group; A C ₆ -C ₃₀ aryloxy group optionally substituted by deuterium, a halogen, an amino group, a nitrile group, a nitro group; A C _{6 -50} aryl group unsubstituted or substituted with a halogen, an amino group, a nitrile group, or a nitro group; Or a deuterium, a halogen, an amino group, a nitrile group, a nitro group a substituted or unsubstituted C _{2 -50} heteroaryl group,
a and b each independently represents an integer of 0 to 3,
m is independently 0 or 1; The method according to claim 1,
A compound represented by any one of the following formulas (1-1) to (1-4):
[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

X, Ar ₁ , Ar ₂ , R ₁ to R ₁₁ , a and b are as defined in the above formula (1). The method according to claim 1,
A compound represented by any one of the following formulas:

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An organic light emitting device comprising at least one layer of an organic material containing an anode, a cathode, and a compound according to claim 1 between two electrodes. 5. The method of claim 4,
Wherein the organic material layer contains the compound of claim 1 as a light emitting host or a dopant. 5. The method of claim 4,
Wherein the organic material layer is an electron transporting layer or a hole blocking layer.

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