KR102180745B1 - Multicyclic compound including nitrogen and organic light emitting device using the same - Google Patents

Abstract

The present invention relates to a nitrogen-containing polycyclic compound and an organic light emitting device comprising the same.

Description

Polycyclic compound containing nitrogen and organic light emitting device using the same {MULTICYCLIC COMPOUND INCLUDING NITROGEN AND ORGANIC LIGHT EMITTING DEVICE USING THE SAME}

The present invention relates to a novel nitrogen-containing polycyclic compound and an organic light-emitting device comprising the same.

An electroluminescent device is a type of self-luminous display device, and has advantages in that it has a wide viewing angle, excellent contrast, and a fast response speed.

The organic light emitting device has a structure in which an organic thin film is disposed between two electrodes. When a voltage is applied to the organic light-emitting device having such a structure, electrons and holes injected from the two electrodes are combined in the organic thin film to form a pair and then emit light while disappearing. The organic thin film may be composed of a single layer or multiple layers as necessary.

The material of the organic thin film may have a light emitting function if necessary. For example, as the organic thin film material, a compound capable of constituting a light emitting layer by itself may be used, or a compound capable of serving as a host or a dopant of the host-dopant-based light emitting layer may be used. In addition, as a material of the organic thin film, a compound capable of performing a role of hole injection, hole transport, electron blocking, hole blocking, electron transport, or electron injection may be used.

In order to improve the performance, life, or efficiency of an organic light emitting device, the development of a material for an organic thin film is continuously required.

The present invention provides a novel nitrogen-containing polycyclic compound and an organic light-emitting device comprising the same.

The present invention provides compounds of formula 1:

In Formula 1,

R ₁ to R ₉ are the same as or different from each other, and each independently hydrogen; halogen; C ₁ to C ₆₀ linear or branched substituted or unsubstituted alkyl; C ₂ to C ₆₀ straight or branched substituted or unsubstituted alkenyl; C ₂ to C ₆₀ straight or branched substituted or unsubstituted alkynyl; C ₁ to C ₆₀ linear or branched substituted or unsubstituted alkoxy; C ₆ to C ₆₀ linear or branched substituted or unsubstituted aryloxy; C ₃ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted cycloalkyl; C ₂ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted heterocycloalkyl; C ₆ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted aryl; C ₂ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted heterocyclic group; A substituted or unsubstituted C ₁₀ to C ₆₀ spiro group; C ₁ to C ₂₀ substituted or unsubstituted alkylamine; C ₆ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted arylamine; And C ₂ to C ₆₀ is selected from the group consisting of monocyclic or polycyclic substituted or unsubstituted heteroarylamine, these may further form a ring with an adjacent substituent.

In addition, the present invention provides an organic light-emitting device comprising an anode, a cathode, and at least one organic material layer provided between the anode and the cathode, wherein at least one of the organic material layers comprises the compound of Formula 1 .

The compound described herein can be used as a material for an organic material layer of an organic light emitting device. The compound may serve as a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, and the like in the organic light emitting device.

1 to 3 illustrate a stacking sequence of an electrode and an organic material layer of an organic light emitting device according to exemplary embodiments of the present invention.

Hereinafter, the present invention will be described in detail.

The compound described herein may be represented by Formula 1. Specifically, the compound of Formula 1 may be used as an organic material layer material of an organic light-emitting device due to the structural characteristics of the core structure and the substituent as described above. More specifically, due to the combination of nitrogen-nitrogen adjacent to each other in the indazole group of the compound of Formula 1, it can have excellent electron transport ability compared to the triazole group used as an organic material layer material of an organic light emitting device, and use a triazole group. It can also solve the problem of shortening the lifespan, which is a disadvantage of organic light emitting devices.

In the present specification, "substituted or unsubstituted" refers to C ₁ to C ₆₀ linear or branched alkyl; C ₂ to C ₆₀ straight or branched alkenyl; C ₂ to C ₆₀ straight or branched alkynyl; C ₃ to C ₆₀ monocyclic or polycyclic cycloalkyl; C ₂ to C ₆₀ monocyclic or polycyclic heterocycloalkyl; C ₆ to C ₆₀ monocyclic or polycyclic aryl; C ₂ to C ₆₀ monocyclic or polycyclic heterocyclic group; A spiro group of C ₁₀ to C ₆₀ ; C ₁ to C ₂₀ alkylamine; C ₆ to C ₆₀ monocyclic or polycyclic arylamine; And C ₂ to C _{60 It} means unsubstituted or substituted with one or more substituents selected from the group consisting of monocyclic or polycyclic heteroarylamine. The additional substituents may be further substituted.

In the present specification, alkyl includes a linear or branched chain having 1 to 60 carbon atoms, and may be further substituted by other substituents. The number of carbon atoms of the alkyl may be 1 to 60, specifically 1 to 40, more specifically 1 to 20.

In the present specification, alkenyl includes a linear or branched chain having 2 to 60 carbon atoms, and may be further substituted by other substituents. The number of carbon atoms of alkenyl may be 2 to 60, specifically 2 to 40, more specifically, 2 to 20.

In the present specification, alkynyl includes a straight or branched chain having 2 to 60 carbon atoms, and may be further substituted by other substituents. The number of carbon atoms of the alkynyl may be 2 to 60, specifically 2 to 40, more specifically, 2 to 20.

In the present specification, cycloalkyl includes monocyclic or polycyclic having 3 to 60 carbon atoms, and may be further substituted by other substituents. Here, the polycyclic refers to a group in which cycloalkyl is directly linked or condensed with another ring group. Here, the other cyclic group may be a cycloalkyl, but may be a different type of cyclic group such as heterocycloalkyl, aryl, heterocycle, and the like. The number of carbon atoms of the cycloalkyl may be 3 to 60, specifically 3 to 40, and more specifically 5 to 20.

In the present specification, heterocycloalkyl includes S, O, N, or Si as a heteroatom, includes monocyclic or polycyclic having 2 to 60 carbon atoms, and may be further substituted by other substituents. Here, the polycyclic means a group in which heterocycloalkyl is directly connected or condensed with another ring group. Here, the other cyclic group may be a heterocycloalkyl, but may be a different type of cyclic group such as cycloalkyl, aryl, heterocycle, and the like. The number of carbon atoms of the heterocycloalkyl may be 2 to 60, specifically 2 to 40, and more specifically 3 to 20.

In the present specification, aryl includes monocyclic or polycyclic having 6 to 60 carbon atoms, and may be further substituted by other substituents. Here, the polycyclic refers to a group in which aryl is directly connected or condensed with another ring group. Here, the other cyclic group may be an aryl, but other types of cyclic groups such as cycloalkyl, heterocycloalkyl, heterocycle, and the like may be used. The number of carbon atoms of the aryl may be 6 to 60, specifically 6 to 40, and more specifically 6 to 25. Specific examples of aryl include phenyl, biphenyl, triphenyl, naphthyl, anthryl, chrysenyl, phenanthrenyl, perylenyl, fluoranthenyl, triphenylenyl, phenalenyl, pyrenyl, tetrasenyl, pentacenyl, Fluorenyl, indenyl, acenaphthylenyl, fluorenyl, and the like, and condensed rings thereof, but are not limited thereto.

In the present specification, the heterocyclic group includes S, O, N, or Si as a heteroatom, includes a monocyclic or polycyclic having 2 to 60 carbon atoms, and may be further substituted by other substituents. Heteroaryl is included in the range of a heterocyclic group, and is a heteroaromatic ring group. Here, polycyclic means a group in which a heterocyclic group is directly connected or condensed with another ring group. Here, the other cyclic group may be a heterocyclic group, but other types of cyclic groups such as cycloalkyl, heterocycloalkyl, aryl, etc. may be used. The number of carbon atoms of the heterocyclic group may be 2 to 60, specifically 2 to 40, and more specifically 3 to 25. Specific examples of the heterocyclic group include pyridyl, pyrrolyl, pyrimidyl, pyridazinyl, furanyl, thienyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, Furazanyl, oxadiazolyl, thiadiazolyl, dithiazolyl, tetrazolyl, pyranyl, thiopyranyl, diazinyl, oxazinyl, thiazinyl, dioxynyl, triazinyl, tetrazinyl, quinolyl, iso Quinolyl, quinazolinyl, isoquinazolinyl, naphthyridyl, acridinyl, phenanthridinyl, imidazopyridinyl, diazanaphthalenyl, triazainden, indolyl, indolizinyl, benzothiazolyl, Benzoxazolyl, benzoimidazolyl, benzothiophene group, benzofuran group, dibenzothiophene group, dibenzofuran group, carbazolyl, benzocarbazolyl, phenazinyl, etc. and condensed rings thereof, but limited to this It does not become.

In the present specification, the spiro group is a group including a spiro structure and may have 15 to 60 carbon atoms. For example, the spiro group may include a structure in which a 2,3-dihydro-1H-indene group or a cyclohexane group is spiro bonded to a fluorene group. Specifically, the spiro group includes a group of the following structural formula.

In the present specification, examples of the monovalent group described above may be applied except that the group described as a divalent group such as an arylene, heteroarylene, or divalent spiro group is a divalent group.

According to an exemplary embodiment of the present invention, R ₁ in Formula 1 is C ₃ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted cycloalkyl; C ₂ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted heterocycloalkyl; C ₆ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted aryl; C ₂ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted heterocyclic group; Or a substituted or unsubstituted C ₁₀ to C ₆₀ spiro group.

According to an exemplary embodiment of the present invention, R ₁ in Formula 1 is C ₆ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted aryl; C ₂ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted heterocyclic group; Or a substituted or unsubstituted C ₁₀ to C ₆₀ spiro group.

According to an exemplary embodiment of the present invention, R ₁ in Formula 1 is C ₆ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted aryl; Or a C ₂ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted heterocyclic group.

According to an exemplary embodiment of the present invention, Chemical Formula 1 may be represented by the following Chemical Formula 2.

[Formula 2]

In Formula 2,

R ₂ to R ₉ are as defined in Formula 1,

L is a C ₆ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted arylene; Or C ₂ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted heteroarylene,

Ar is C ₆ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted aryl; Or C ₂ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted heterocyclic group,

m is an integer from 0 to 3, n is an integer from 1 to 3,

When m is 2 or more, L is the same as or different from each other, and when n is 2 or more, Ar is the same or different from each other.

According to an exemplary embodiment of the present invention, in Formula 2, m is 1 or 2.

According to an exemplary embodiment of the present invention, in Formula 2, L is a C ₆ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted arylene.

According to an exemplary embodiment of the present invention, in Formula 2, L is a substituted or unsubstituted, tricyclic or less arylene or tricyclic or less heteroarylene. When L is tricyclic or less arylene or heteroarylene, it is advantageous in terms of controlling the band gap of the compound. In general, when the ring directly bonded to the electron acceptor increases, the band gap decreases.

According to an exemplary embodiment of the present invention, in Formula 2, L is a substituted or unsubstituted, monocyclic arylene or monocyclic heteroarylene.

According to an exemplary embodiment of the present invention, in Formula 2, L is a substituted or unsubstituted, tricyclic or less arylene.

According to an exemplary embodiment of the present invention, in Formula 2, L is a substituted or unsubstituted phenylene, a substituted or unsubstituted naphthylene, or a substituted or unsubstituted anthrylene.

According to an exemplary embodiment of the present invention, in Formula 2, L is phenylene, naphthylene, or anthrylene.

According to an exemplary embodiment of the present invention, in Formula 2, L is a substituted or unsubstituted phenylene.

According to an exemplary embodiment of the present invention, in Formula 2, L is phenylene.

According to an exemplary embodiment of the present invention, in Formula 2, L is a substituted or unsubstituted, and 3 or less N-containing heteroarylene.

According to an exemplary embodiment of the present invention, in Formula 2, L is a substituted or unsubstituted monocyclic N-containing heteroarylene.

According to an exemplary embodiment of the present invention, in Formula 2, L is unsubstituted phenylene, substituted or unsubstituted naphthylene, or substituted or unsubstituted anthrylene.

According to an exemplary embodiment of the present invention, in Formula 2, L is phenylene or a 6-membered monocyclic N-containing heteroarylene, and the core structure of Formula 1 and Ar are substituted at the para or meta position of L.

According to an exemplary embodiment of the present invention, in Formula 2, L is phenylene or a 6-membered monocyclic N-containing heteroarylene, and the core structure of Formula 1 and Ar are substituted at the para position of L.

According to an exemplary embodiment of the present invention, in Formula 2, Ar is C ₆ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted aryl; Or a C ₂ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted N-containing heterocyclic group.

According to an exemplary embodiment of the present invention, in Formula 2, Ar is substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthryl, substituted or unsubstituted phenanthrenyl, substituted Or unsubstituted triphenylenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidyl, substituted or unsubstituted triazinyl, substituted or unsubstituted quinolyl, or substituted or unsubstituted isoquinolyl. . Ar is C ₆ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted aryl; Or it may be substituted with a C ₂ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted N-containing heterocyclic group.

According to an exemplary embodiment of the present invention, in Formula 2, Ar is phenyl, naphthyl, anthryl, phenanthrenyl, triphenylenyl, pyridyl, pyrimidyl, triazinyl, quinolyl, or isoquinolyl , These are C ₆ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted aryl; Or a C ₂ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted N-containing heterocyclic group substituted or unsubstituted.

According to an exemplary embodiment of the present invention, in Formula 2, Ar is phenyl, naphthyl, anthryl, phenanthrenyl, triphenylenyl, pyridyl, pyrimidyl, triazinyl, quinolyl, or isoquinolyl , These are phenyl, biphenyl, naphthyl, anthryl, phenanthrenyl, triphenylenyl, phenylnaphthyl, phenylanthryl, naphthylphenyl, anthrylphenyl, naphthylanthryl, anthrylnaphthyl, phenylphenanthrenyl , Phenanthrenylphenyl, pyridyl, pyrimidyl, triazinyl, phenylpyridyl, pyridylphenyl, phenylpyrimidyl, pyrimidylphenyl, phenyltriazinyl, triazinylphenyl, quinolyl, isoquinolyl, quinolylphenyl, It is unsubstituted or substituted with one or two or more substituents selected from the group consisting of phenylquinolyl, isoquinolylphenyl, and phenylisoquinolyl.

According to an exemplary embodiment of the present invention, in Formula 2, Ar is a substituted or unsubstituted aryl of three or more rings; Or a C ₂ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted N-containing heterocyclic group.

According to an exemplary embodiment of the present invention, Chemical Formula 1 may be selected from the following Chemical Formulas.

The above-described compounds may be prepared based on the preparation examples described later. In the preparation examples described below, representative examples are described, but if necessary, a substituent may be added or excluded, and the position of the substituent may be changed. In addition, starting materials, reactants, reaction conditions, and the like can be changed based on techniques known in the art. If necessary, changing the type or position of the substituent at the remaining position can be performed by a person skilled in the art using techniques known in the art.

Another exemplary embodiment of the present invention provides an organic light-emitting device comprising the compound of Formula 1 described above. Specifically, the organic light emitting device according to the present invention includes an anode, a cathode, and at least one organic material layer provided between the anode and the cathode, and at least one of the organic material layers includes the compound of Formula 1.

1 to 3 illustrate a stacking sequence of an electrode and an organic material layer of an organic light emitting device according to exemplary embodiments of the present invention. However, it is not intended that the scope of the present invention be limited by these drawings, and the structure of an organic light-emitting device known in the art can be applied to the present invention.

Referring to FIG. 1, an organic light emitting device in which an anode 200, an organic material layer 300, and a cathode 400 are sequentially stacked on a substrate 100 is shown. However, it is not limited to such a structure, and as shown in FIG. 2, an organic light emitting device in which a cathode, an organic material layer, and an anode are sequentially stacked on a substrate may be implemented.

3 illustrates a case in which the organic material layer is a multilayer. The organic light emitting device according to FIG. 3 includes a hole injection layer 301, a hole transport layer 302, a light emitting layer 303, an electron transport layer 304, and an electron injection layer 305. However, the scope of the present invention is not limited by such a lamination structure, and other layers other than the light emitting layer may be omitted, or other necessary functional layers may be further added as necessary.

The organic light-emitting device according to the present invention can be manufactured by materials and methods known in the art, except for including the compound of Formula 1 in at least one of the organic material layers.

The compound of Formula 1 alone may constitute one or more of the organic material layers of the organic light emitting device. However, if necessary, the organic material layer may be formed by mixing with other materials.

The compound of Formula 1 may be used as a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, and the like in an organic light emitting device. The compound of Formula 1 may be used as a material of one or more of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer. As an example, the compound of Formula 1 may be used as a material for an electron injection and/or transport layer of an organic light emitting device. As another example, the compound of Formula 1 may be used as a material for a light emitting layer of an organic light emitting device. As another example, the compound of Formula 1 may be used as a host material for a phosphorescent layer of an organic light emitting device.

In the organic light-emitting device according to the present invention, materials other than the compound of Formula 1 are exemplified below, but these are only for illustration and are not intended to limit the scope of the present invention, and materials known in the art are used. Can be replaced.

Materials having a relatively large work function may be used as the cathode material, and transparent conductive oxides, metals, or conductive polymers may be used.

Materials having a relatively low work function may be used as the cathode material, and metal, metal oxide, or conductive polymer may be used.

As the hole injection material, a known hole injection material may be used. For example, a phthalocyanine compound such as copper phthalocyanine disclosed in U.S. Patent No. 4,356,429 or a phthalocyanine compound disclosed in [Advanced Material, 6, p.677 (1994)] is described. Starburst type amine derivatives, such as TCTA, m-MTDATA, m-MTDAPB, Pani/DBSA (Polyaniline/Dodecylbenzenesulfonic acid: 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 sulfonic acid: Polyaniline/Camphor Sulfonic acid) or PANI/PSS(Polyaniline)/Poly(4-styrene-sulfonate):polyaniline)/poly(4-styrenesulfonate)), etc. may be used.

As the hole transport material, pyrazoline derivatives, arylamine derivatives, stilbene derivatives, triphenyldiamine derivatives, etc. may be used, and low molecular weight or high molecular weight materials may be used.

Electron transport materials include oxadiazole derivatives, anthraquinodimethane and derivatives thereof, benzoquinone and derivatives thereof, naphthoquinone and derivatives thereof, anthraquinone and derivatives thereof, tetracyanoanthraquinodimethane and derivatives thereof, fluorenone Derivatives, diphenyl dicyanoethylene and derivatives thereof, diphenoquinone derivatives, metal complexes of 8-hydroxyquinoline and derivatives thereof, and the like may be used, and not only low-molecular substances but also high-molecular substances may be used.

As the electron injection material, for example, LiF is typically used in the art, but the present invention is not limited thereto.

Red, green, or blue light emitting materials may be used as the light emitting material, and if necessary, two or more light emitting materials may be mixed and used. Further, a fluorescent material may be used as the light emitting material, but may also be used as a phosphorescent material. As the light emitting material, a material that emits light by combining holes and electrons respectively injected from the anode and the cathode may be used, but materials in which the host material and the dopant material are both involved in light emission may be used.

When the compound according to the present invention is used as a phosphorescent host material, those known in the art may be used as the phosphorescent dopant material used together.

For example, phosphorescent dopant materials represented by LL'MX, LL'L"M, LMXX', L ₂ MX and L ₃ M may be used, but the scope of the present invention is not limited by these examples.

Here, L, L', L", X and X'are different bidentate ligands, and M is a metal forming an eight-sided complex.

M can be iridium, platinum, osmium, etc.

L is for sp ² It is an anionic bidentate ligand coordinated to M by carbon and hetero atoms, and X can function to trap electrons or holes. Non-limiting examples of L include 2-(1-naphthyl)benzoxazole, (2-phenylbenzoxazole), (2-phenylbenzothiazole), (2-phenylbenzothiazole), (7,8 -Benzoquinoline), (thienylpyridine), phenylpyridine, benzothienylpyridine, 3-methoxy-2-phenylpyridine, thienylpyridine, tolylpyridine, and the like. Non-limiting examples of X include acetylacetonate (acac), hexafluoroacetylacetonate, salicylidene, picolinate, 8-hydroxyquinolinate, and the like.

More specific examples are shown below, but are not limited to these examples.

Hereinafter, the present invention will be described in more detail through examples, but these are only intended to illustrate the present invention and are not intended to limit the scope of the present invention.

[Production Example 1] Preparation of Compound 1

compound 1-4 Manufacture of

To 100 mL of MC, 59 mL (59.06 mmol) of BCl ₃ was added, and 5 g (53.68 mmol) of aniline was slowly added at 0°C. Maintaining at 0 ℃ AlCl ₃ 7.87g (59.06mmol) was added at once, 2-fluorobenzonitrile 7.8g (64.43mmol) was slowly added and refluxed for 16 hours. After lowering the temperature to 0°C, 100 mL of 2N-HCl was added and refluxed at 80°C for 2 hours. When the reaction was completed, the mixture was extracted using MC and H ₂ O, and then separated and purified by column chromatography using Hex/EA to obtain 4.8 g (54%) of the title compound 1-4 .

compound 1-3 Manufacture of

Compound 1-4 3g (13.94mmol) was added to 30mL of hydrazine and refluxed at 120°C for 3 hours. When the reaction was completed, H ₂ O was added and the resulting solid was filtered to obtain 2.86 g (96%) of the target compound 1-3 .

compound 1-2 Manufacture of

After dissolving compound 1-3 2.8g (13.38mmol) and p-toluenesulfonic acid 0.15g (0.80mmol) in 30 mL of ethanol, 2.97g of 4-bromobenzaldehyde at 30℃ ( 16.06mmol) was added and refluxed at 50°C for 1 hour. When the reaction was completed, the solid was filtered with ethanol, and then separated and purified by column chromatography using Hex/EA to obtain 2.8 g (56%) of the title compound 1-2 .

compound 1-1 Manufacture of

After dissolving 2.8g (7.44mmol) of Compound 1-2 in 30mL of DMF, 0.14g (0.74mmol) of CuI was added and refluxed at 100°C for 24 hours. When the reaction was completed, the mixture was extracted with ethyl acetate and H ₂ O, and then separated and purified by column chromatography using Hex/EA to obtain 1.75 g (63%) of the title compound 1-1 .

compound One Manufacture of

Compound 1-1 1.75g (4.68mmol) was dissolved in 20 mL of toluene, 4 mL of ethanol, and 4 mL of H ₂ O, Pd(PPh ₃ ) ₄ 0.27 g (0.234 mmol), K ₂ CO ₃ 1.94 g (14.03 mmol), 2 -(9,10-di(naphthalen-2-yl)anthracen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 3.38g (6.08mmol) It refluxed at 80°C for 12 hours. When the reaction is complete, filter with H ₂ O and methanol, and extract with dichloromethane and H ₂ O. After extraction, separation and purification by column chromatography using EA/Hex gave 2.64 g (78%) of the title compound 1 .

[Production Examples 2 to 22]

A compound having the structure of Table 1 as Ar of Formula 2 was prepared in the same manner as in Preparation Example 1.

Manufacturing example No. Compound No. Ar Manufacturing Example 2 Compound 2

Manufacturing Example 3 Compound 3

Manufacturing Example 4 Compound 4

Manufacturing Example 5 Compound 7

Manufacturing Example 6 Compound 9

Manufacturing Example 7 Compound 11

Manufacturing Example 8 Compound 13

Manufacturing Example 9 Compound 14

Manufacturing Example 10 Compound 17

Manufacturing Example 11 Compound 20

Manufacturing Example 12 Compound 23

Manufacturing Example 13 Compound 26

Manufacturing Example 14 Compound 28

Manufacturing Example 15 Compound 30

Manufacturing Example 16 Compound 32

Manufacturing Example 17 Compound 33

Manufacturing Example 18 Compound 34

Manufacturing Example 19 Compound 36

Manufacturing Example 20 Compound 38

Manufacturing Example 21 Compound 39

Manufacturing Example 22 Compound 42

[Production Example 23] Preparation of Compound 43

compound 43-4 Manufacture of

To 100 mL of MC, 59 mL (59.06 mmol) of BCl ₃ was added, and 5 g (53.68 mmol) of aniline was slowly added at 0°C. Maintaining at 0 ℃ AlCl ₃ 7.87g (59.06mmol) was added at once, 2-fluorobenzonitrile 7.8g (64.43mmol) was slowly added and refluxed for 16 hours. After lowering the temperature to 0°C, 100 mL of 2N-HCl was added and refluxed at 80°C for 2 hours. When the reaction was completed, the mixture was extracted using MC and H ₂ O, and then separated and purified by column chromatography using Hex/EA to obtain 4.8 g (54%) of the title compound 43-4 .

compound 43-3 Manufacture of

Compound 43-4 3g (13.94mmol) was added to 30mL of hydrazine and refluxed at 120°C for 3 hours. When the reaction was completed, H ₂ O was added to filter the resulting solid to obtain 2.86 g (96%) of the title compound 43-3 .

compound 43-2 Manufacture of

After dissolving compound 43-3 2.8g (13.38mmol) and p-toluenesulfonic acid 0.15g (0.80mmol) in 30 mL of ethanol, 2.97g (16.06mmol) 3-bromobenzaldehyde was added at 30℃ and refluxed at 50℃ for 1 hour. I did. When the reaction was completed, the solid was filtered with ethanol, and then separated and purified by column chromatography using Hex/EA to obtain 2.8 g (56%) of the title compound 43-2 .

compound 43-1 Manufacture of

After dissolving 2.8g (7.44mmol) of compound 43-2 in 30mL of DMF, 0.14g (0.74mmol) of CuI was added and refluxed at 100°C for 24 hours. When the reaction was completed, the mixture was extracted with ethyl acetate and H ₂ O, and then separated and purified by column chromatography using Hex/EA to obtain 1.75 g (63%) of the title compound 43-1 .

compound 43 Manufacture of

After dissolving 1.75g (4.68mmol) of compound 43-1 in 20mL of toluene, 4mL of ethanol, and 4mL of H ₂ O, Pd(PPh ₃ )4 0.27g (0.234mmol), K2CO3 1.94g (14.03mmol), 2-(9) ,10-di(naphthalen-2-yl)anthracen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolein 3.38g (6.08mmol) was added at 80℃ It was refluxed for 12 hours. When the reaction is complete, filter with H ₂ O and methanol, and extract with dichloromethane and H ₂ O. After extraction, separation and purification by column chromatography using EA/Hex gave 2.64g (78%) of the title compound 43 .

[Production Examples 24-44]

A compound having the structure of Table 2 as Ar of Formula 2 was prepared in the same manner as in Preparation Example 23.

Manufacturing example No. Compound No. Ar Manufacturing Example 24 Compound 43

Manufacturing Example 25 Compound 44

Manufacturing Example 26 Compound 45

Manufacturing Example 27 Compound 46

Manufacturing Example 28 Compound 50

Manufacturing Example 29 Compound 53

Manufacturing Example 30 Compound 55

Manufacturing Example 31 Compound 58

Manufacturing Example 32 Compound 59

Manufacturing Example 33 Compound 60

Manufacturing Example 34 Compound 62

Manufacturing Example 35 Compound 64

Manufacturing Example 36 Compound 65

Manufacturing Example 37 Compound 67

Manufacturing Example 38 Compound 70

Manufacturing Example 39 Compound 72

Manufacturing Example 40 Compound 74

Manufacturing Example 41 Compound 75

Manufacturing Example 42 Compound 76

Manufacturing Example 43 Compound 81

Manufacturing Example 44 Compound 84

The synthesis confirmation results of the compounds prepared in the above Preparation Examples are shown in Table 3 below.

compound
No. F ound c alculated One δ= 8.32(1H,d), 8.16(1H,d), 8.13(1H,d), 8.00(4H,d), 7.97(1H,d), 7.92(3H,d), 7.91(2H,d) , 7.85(2H,d), 7.84(1H,d), 7.83(1H,d), 7.73(2H, d), 7.62(1H,t), 7.61(1H,d), 7.59(4H,t), 7.58(3H,m), 7.48(1H,t), 7.39(2H,t), 7.25(2H,d) 723.86 723.27 2 δ= 9.15(1H,s), 8.93(2H,d), 8.32(1H,d), 8.18(1H,d), 8.16(1H,d), 8.12(2H,d), 8.04(1H,d) , 7.92(1H,d), 7.88(2H,t), 7.85(2H,d), 7.84(1H,d), 7.83(1H,t), 7.82(2H,t), 7.62(1H,t), 7.58(1H,t), 7.48(1H,t), 7.25(2H,d) 521.61 521.19 3 δ= 8.32(1H,d), 8.28(4H,d), 8.16(1H,d), 7.92(1H,d), 7.85(4H,d), 7.84-7.83(2H,m), 7.62(1H, t), 7.58(1H,t), 7.51-7.41(7H,m) 526.59 526.19 4 δ= 9.09(2H,s), 8.49(2H,d), 8.32(1H,d), 8.16(1H,d), 8.00(4H,d), 7.92(3H,d), 7.85(4H,d) , 7.84(1H,d), 7.83(1H,t), 7.62(1H,t), 7.59(4H,t), 7.50(1H,t), 7.48(1H,t) 626.71 626.22 7 δ= 8.32(1H,d), 8.16(1H,d), 8.00(2H,d), 7.92(2H,d), 7.91(4H,d), 7.85(2H,d), 7.84(1H,d) , 7.83(1H,t), 7.73(1H,d), 7.62(1H,t), 7.59(2H,t), 7.58(2H,s), 7.48(1H,t), 7.39(4H,t) 7.25 (2H,d) 597.71 597.22 9 δ= 8.32(1H,d), 8.18(1H,d), 7.92(1H,d), 7.85(8H,m), 7.84(1H,d), 7.83(1H,t), 7.62(1H,t) , 7.58(1H,t), 7.51-7.41(11H,m), 7.25(4H,d) 678.78 678.25 11 δ= 8.83(2H,d), 8.38(2H,d), 8.32(1H,d), 8.21(2H,d), 8.16(1H,d), 8.02(2H,d), 7.92(1H,d) , 7.85(8H,m), 7.84(1H,d), 7.83(1H,t), 7.66(2H,t), 7.62(1H,t), 7.58(3H,t), 7.48(1H,t), 7.25(4H,d) 780.87 780.27 13 δ= 8.32(1H,d), 8.23(1H,s), 8.16(1H,d), 7.92(1H,d), 7.85(4H,d), 7.84(1H,d), 7.83(1H,d) , 7.79(4H,d), 7.62(1H,t), 7.58(1H,t), 7.51-7.41(7H,m) 525.60 525.20 14 δ= 8.34(2H,s), 8.32(1H,d), 8.23(1H,s), 8.16(1H,d), 8.00(4H,d), 7.92(3H,d), 7.87(2H,d) , 7.85(4H,d), 7.84(1H,d), 7.83(1H,t), 7.62(1H,t), 7.59(4H,t), 7.58(1H,t), 7.48(1H,t) 625.72 625.23 17 δ= 8.83(2H,d), 8.38(2H,d), 8.37(2H,d), 8.32(1H,d), 8.23(1H,s), 8.16(1H,d), 8.02(2H,d) , 7.92(1H,d), 7.85(4H,d), 7.84(1H,d), 7.83(1H,t), 7.66(2H,t), 7.62(1H,t), 7.58(3H,t), 7.48(1H,t) 627.69 627.22 20 δ= 8.81(4H,d), 8.50(2H,d), 8.33(4H,d), 8.32(1H,d), 8.23(1H,s), 8.16(1H,d), 7.92(1H,d) , 7.85(4H,d), 7.84(1H,d), 7.83(1H,t), 7.62(1H,t), 7.58(1H,t), 7.51(2H,t), 7.48(1H,t), 7.26(2H,d), 7.00(2H,t) 679.77 679.25 23 δ= 8.32(1H,d), 8.30(4H,d), 8.20(2H,s), 8.16(1H,d), 7.92(1H,d), 7.85(2H,d), 7.84(1H,d) , 7.83(1H,t), 7.62(1H,t), 7.58(1H,t), 7.54-7.47(7H,m), 7.25(2H,d) 524.61 524.20 26 δ= 8.55(2H,d), 8.46(2H,d), 8.32(1H,d), 8.20(2H,s), 8.16(1H,d), 8.10(2H,d), 8.08(2H,d) , 7.92(1H,d), 7.85(2H,d), 7.84(1H,d), 7.83(1H,t), 7.64(2H,t), 7.62(1H,t), 7.58(1H,t), 7.55(4H,t), 7.48(1H,t), 7.25(2H,d) 624.73 624.23 28 δ= 8.93(4H,d), 8.44(2H,s), 8.32(1H,d), 8.20(2H,s), 8.16(1H,d), 8.12(4H,d), 7.92(1H,d) , 7.88(4H,t), 7.85(2H,d), 7.84(1H,d), 7.83(1H,t), 7.82(4H,t), 7.62(1H,t), 7.58(1H,t), 7.48(1H,t), 7.25(2H,d) 724.85 724.26 30 δ= 8.84(8H,d), 8.50(2H,d), 8.32(1H,d), 8.20(2H,s), 8.16(1H,d), 7.92(1H,d), 7.85(2H,d) , 7.84(1H,d), 7.83(1H,t), 7.62(1H,t), 7.58(1H,t), 7.51(2H,t), 7.48(1H,t), 7.26(2H,d), 7.25(2H,d), 7.00(2H,t) 678.78 678.25 32 δ= 8.84(8H,d), 8.32(1H,d), 8.20(2H,s), 8.16(1H,d), 8.10(2H,d), 8.06(2H,d), 7.98(2H,d) , 7.92(1H,d), 7.85(2H,d), 7.84(1H,d), 7.83(1H,t), 7.78(2H,t), 7.62(1H,t), 7.60(2H,t), 7.58(1H,t), 7.48(1H,t), 7.35(2H,d), 7.25(2H,d) 778.90 778.28 33 δ= 8.81(2H,d), 8.32(1H,d), 8.30(2H,d), 8.20(2H,s), 8.16(1H,d), 7.92(1H,d), 7.88(2H,d) , 7.84(1H,d), 7.83(1H,t), 7.62(1H,t), 7.58(1H,t), 7.54(2H,t), 7.52-7.41(7H,m) 524.61 524.20 34 δ= 8.85(1H,s), 8.81(2H,d), 8.38(1H,d), 8.32(1H,d), 8.20(2H,s), 8.16(1H,d), 8.00(4H,d) , 7.95(1H,d), 7.92(2H,d), 7.88(2H,d), 7.84(1H,d), 7.83(1H,t), 7.73(1H,d), 7.62(1H,t), 7.59(4H,t), 7.58(2H,t), 7.48(1H,t) 624.73 624.23 36 δ= 8.81(2H,d), 8.55(2H,d), 8.46(1H,d), 8.42(1H,d), 8.32(1H,d), 8.20(2H,s), 8.16(1H,d) , 8.10(1H,d), 8.08(2H,d), 8.04(1H,d), 7.92(1H,d), 7.88(2H,d), 7.84(1H,d), 7.83(1H,t), 7.64(1H,t), 7.62(1H,t), 7.61(1H,t), 7.58(1H,t), 7.55(4H,t), 7.48(1H,t) 624.73 264.23 38 δ= 8.93(4H,d), 8.81(2H,d), 8.44(1H,s), 8.32(1H,d), 8.20(2H,s), 8.16(1H,d), 8.12(4H,d) , 7.93(1H,s), 7.92(1H,d), 7.88(6H,m), 7.84(1H,d), 7.83(1H,t), 7.82(4H,t), 7.62(1H,t), 7.58(1H,t), 7.48(1H,t) 724.85 724.26 39 δ= 8.81(4H,d), 8.32(1H,d), 8.20(2H,s), 8.16(1H,d), 7.92(1H,d), 7.88(4H,t), 7.84(1H,d) , 7.83(1H,t), 7.62(1H,t), 7.58(1H,t), 7.52-7.48(9H,m), 7.41(2H,t), 7.25(4H,d) 676.81 676.26 42 δ= 8.84(4H,d), 8.81(4H,d), 8.32(1H,d), 8.20(2H,s), 8.16(1H,d), 8.10(2H,d), 8.06(2H,d) , 7.98(2H,d), 7.92(1H,d), 7.88(4H,d), 7.84(1H,d), 7.83(1H,t), 7.78(2H,t), 7.62-7.58(4H,m ), 7.48(1H,t), 7.35(2H,d) 778.90 778.28 43 δ= 8.32(1H,d), 8.24(1H,d), 8.16(1H,d), 8.13(1H,s), 8.00(4H,d), 7.97(1H,d), 7.92(3H,d) , 7.91(2H,d), 7.84(1H,d), 7.83(1H,t), 7.73(2H,d), 7.70(1H,s), 7.62(1H,t), 7.61(1H,d), 7.59(4H,t), 7.58(2H,t), 7.57(1H,t), 7.48(2H,t), 7.39(2H,t) 723.27 723.86 44 δ= 9.15(1H,s), 8.93(2H,d), 8.32(1H,d), 8.24(1H,d), 8.18(1H,d), 8.16(1H,d), 8.12(2H,d) , 8.04(1H,d), 7.92(1H,d), 7.88(2H,t), 7.84(1H,d), 7.83(1H,t), 7.82(2H,t), 7.70(1H,s), 7.62(1H,t), 7.58(1H,t), 7.571H,t), 7.48(2H,t) 521.61 521.19 45 δ= 8.32(1H,d), 8.28(4H,d), 8.24(2H,d), 8.16(1H,d), 7.92(1H,d), 7.84(1H,d), 7.83(1H,t) , 7.70(1H,s), 7.62(1H,t), 7.58(1H,t), 7.57(1H,t), 7.5-7.41(6H,m), 7.48(1H,t) 526.59 526.19 46 δ= 9.09(2H,s), 8.49(2H,d), 8.32(1H,d), 8.24(2H,d), 8.16(1H,d), 8.00(4H,d), 7.92(3H,d) , 7.84(1H,d), 7.83(1H,t), 7.70(1H,s), 7.62(1H,t), 7.59(4H,t), 7.57(1H,t), 7.58(1H,t), 7.48(1H,t) 626.71 626.22 50 δ= 8.93(4H,d), 8.32(1H,d), 8.24(2H,d), 8.16(1H,d), 8.12(4H,d), 7.93(2H,s), 7.92(1H,d) , 7.88(4H,t), 7.84(1H,d), 7.83(1H,t), 7.82(4H,t), 7.70(1H,s), 7.62(1H,t), 7.58(1H,t), 7.57(1H,t), 7.48(1H,t) 726.82 726.25 51 δ= 8.32(1H,d), 8.24(2H,d), 8.16(1H,d), 7.92(1H,d), 7.85(4H,d), 7.84(1H,d), 7.83(1H,t) , 7.70(1H,s), 7.62(1H,t), 7.58(1H,t), 7.57(1H,t), 7.52-7.51(8H,m), 7.48(1H,t), 7.41(2H,t) ), 7.25(4H,d) 678.78 678.25 53 δ= 8.83(2H,d), 8.38(2H,d), 8.32(1H,d), 8.24(2H,d), 8.21(2H,d), 8.16(1H,d), 8.02(2H,d) , 7.92(1H,d), 7.85(4H,d), 7.84(1H,d), 7.83(1H,t), 7.70(1H,s), 7.66(2H,t), 7.62(1H,t), 7.58(3H,t), 7.57(1H,t), 7.48(1H,t), 7.25(4H,d) 780.87 780.27 55 δ= 8.32(1H,d), 8.24(2H,d), 8.23(1H,s), 8.16(1H,d), 7.92(1H,d), 7.84(1H,d), 7.83(1H,t) , 7.79(4H,d), 7.70(1H,s), 7.62(1H,t), 7.58(1H,t), 7.57(1H,t), 7.51-7.41(7H,m) 525.60 525.20 58 δ= 8.55(2H,d), 8.32(1H,d), 8.24(2H,d), 8.23(1H,s), 8.16(1H,d), 8.08(2H,d), 8.04(2H,d) , 7.95(2H,d), 7.92(1H,d), 7.84(1H,d), 7.83(1H,t), 7.70(1H,s), 7.62(1H,t), 7.61(2H,t), 7.58(1H,t), 7.57(1H,t), 7.55(4H,t), 7.48(1H,t) 625.72 625.23 59 δ= 8.83(2H,d), 8.38(2H,d), 8.37(2H,d), 8.32(1H,d), 8.24(2H,d), 8.16(1H,d), 8.23(1H,s) , 8.02(2H,d), 7.92(1H,d), 7.84(1H,d), 7.83(1H,t), 7.70(1H,s), 7.66(2H,d), 7.62(1H,t), 7.58(3H,t), 7.57(1H,t) 7.48(1H,t) 627.69 627.22 60 δ= 8.93(4H,d), 8.32(1H,d), 8.24(2H,d), 8.23(1H,s), 8.16(1H,d), 8.12(4H,d), 7.93(2H,s) , 7.92(1H,d), 7.88(4H,t), 7.84(1H,d), 7.83(1H,t), 7.82(4H,t), 7.70(1H,s), 7.62(1H,t), 7.58(1H,t), 7.57(1H,t), 7.48(1H,t) 725.84 725.26 62 δ= 8.81(4H,d), 8.50(2H,d), 8.32(1H,d), 8.24(1H,d), 8.16(1H,d), 7.92(1H,d), 7.88(4H,d) , 7.84(1H,d), 7.83(1H,t), 7.70(1H,s), 7.66(3H,s), 7.62(1H,t), 7.58(1H,t), 7.57(1H,t), 7.51(2H,t), 7.48(2H,t), 7.26(2H,d), 7.00(2H,t) 677.79 677.26 64 δ= 8.81(4H,d), 8.32(1H,d), 8.24(1H,d), 8.16(1H,d), 8.10(2H,d), 8.06(2H,d), 7.98(2H,d) , 7.92(1H,d), 7.88(4H,d), 7.84(1H,d), 7.83(1H,t), 7.78(2H,t), 7.70(1H,s), 7.66(3H,s), 7.62(1H,t), 7.60(2H,t), 7.58(1H,t), 7.57(1H,t), 7.48(2H,t), 7.35(2H,d) 777.91 777.29 65 δ= 8.32(1H,d), 8.30(4H,d), 8.24(1H,d), 8.20(2H,s), 8.16(1H,d), 7.92(1H,d), 7.84(1H,d) , 7.83(1H,t), 7.70(1H,s), 7.62(1H,t), 7.58(1H,t), 7.57(1H,t), 7.54(4H,t), 7.48(2H,t), 7.47(2H,t) 524.61 524.20 67 δ= 9.15(2H,s), 8.32(1H,d), 8.31(2H,d), 8.29(2H,d), 8.24(1H,d), 8.16(1H,d), 8.06(2H,d) , 7.98(2H,d), 7.92(1H,d), 7.84(1H,d), 7.83(1H,t), 7.78(2H,t), 7.70(1H,s), 7.62(1H,t), 7.60(2H,t), 7.58(1H,t), 7.57(1H,t), 7.48(2H,t) 626.71 626.22 70 δ= 8.32(1H,d), 8.24(1H,d), 8.16(1H,d), 8.00(2H,d), 7.92(2H,d), 7.91(4H,d), 7.84(1H,d) , 7.83(1H,t), 7.73(1H,d), 7.70(1H,s), 7.62(1H,t), 7.59(2H,t), 7.58(2H,d), 7.57(1H,t), 7.48(2H,t), 7.39(4H,t) 597.71 597.22 72 δ= 8.84(8H,d), 8.50(2H,d), 8.32(1H,d), 8.24(1H,d), 8.20(2H,s), 8.16(1H,d), 7.92(1H,d) , 7.84(1H,d), 7.83(1H,t), 7.70(1H,s), 7.62(1H,t), 7.58(1H,t), 7.57(1H,t), 7.51(2H,t), 7.48(2H,t), 7.26(2H,d), 7.00(2H,t) 678.78 678.25 74 δ= 8.84(8H,d), 8.32(1H,d), 8.24(1H,d), 8.20(1H,s), 8.16(1H,d), 8.10(2H,d), 8.06(2H,d) , 7.98(2H,d), 7.92(1H,d), 7.70(1H,s), 7.62(1H,t), 7.60(2H,t), 7.58(1H,t), 7.57(1H,t), 7.48(2H,t), 7.35(2H,d) 778.90 778.28 75 δ= 8.32(1H,d), 8.30(3H,d), 8.26(1H,t), 8.21(1H,s), 8.20(2H,d), 8.16(1H,d), 7.92(1H,d) , 7.84(1H,d), 7.83(1H,t), 7.62(1H,t), 7.60(1H,t), 7.58(1H,t), 7.54(2H,t), 7.52(2H,d), 7.51-7.41(4H,m) 524.61 524.20 76 δ= 8.85(1H,s), 8.38(1H,d), 8.32(1H,d), 8.30(1H,d), 8.26(1H,d), 8.21(1H,s), 8.20(2H,s) , 8.16(1H,d), 8.00(4H,d), 7.95(1H,d), 7.92(2H,d), 7.84(1H,d), 7.83(1H,t), 7.73(1H,d), 7.62(1H,t), 7.60(1H,t), 7.59(4H,t), 7.58(2H,s), 7.48(1H,t) 624.73 624.23 81 δ= 8.81(2H,d), 8.32(1H,d), 8.30(1H,d), 8.26(1H,d), 8.21(1H,s), 8.20(2H,s), 8.16(1H,d) , 7.92(1H,d), 7.88(2H,d), 7.84(1H,d), 7.83(1H,t), 7.62(1H,t), 7.60(1H,t), 7.58(1H,t), 7.52-7.51(8H,m), 7.41(2H,t), 7.48(1H,t), 7.25(4H,d) 676.81 676.26 84 δ= 8.84(4H,d), 8.81(2H,d), 8.32(1H,d), 8.30(1H,d), 8.20(2H,s), 8.26(1H,d), 8.16(1H,d) , 8.10(2H,d), 8.06(2H,d), 7.98(2H,t), 7.92(1H,d), 7.88(2H,d), 7.84(1H,d), 7.83(1H,t), 7.62(1H,t), 7.60(3H,t), 7.58(1H,t), 7.48(1H,t), 7.35(2H,d) 778.90 778.28

Example : OLED Device fabrication

[Comparative Example]

The transparent electrode ITO thin film obtained from OLED glass (manufactured by Samsung-Corning) was subjected to ultrasonic cleaning by sequentially using trichloroethylene, acetone, ethanol, and distilled water, and then stored in isopropanol and used.

Next, the ITO substrate is installed in the substrate folder of the vacuum deposition equipment, and the following 4,4',4"-tris(N,N-(2-naphthyl)-phenylamino)triphenyl amine: 2- I put in TNATA.

Subsequently, after evacuating until the degree of vacuum in the chamber reached 10 ^-6 torr, a current was applied to the cell to evaporate 2-TNATA to deposit a hole injection layer having a thickness of 600 Å on the ITO substrate. The following N,N'-bis(α-naphthyl)-N,N'-diphenyl-4,4'-diamine: NPB is added to another cell in the vacuum deposition equipment, and a current is applied to the cell to evaporate to the hole injection layer. A 300Å thick hole transport layer was deposited.

After forming the hole injection layer and the hole transport layer as described above, a phosphorescent green light emitting material having the following structure was deposited on the light emitting layer. A green light emitting host material, 4,4'-bis(carbazol-9-yl)biphenyl (4,4'-bis(carbazol-9-yl)biphenyl; CBP), is 350 Å thick in one cell in a vacuum evaporation equipment. A green light emitting dopant material, Tris (2-phenylpyridine) iridium (III): Ir (ppy) ₃ ) was vacuum-deposited by 10% compared to the host material.

Then, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (2,9-dimethyl-4,7-diphenyl-1,10), which is a major blocking layer material as follows, as a major blocking layer. -Phenanthroline; BCP) was deposited to a thickness of 50 Å, and the following Tris (8-hydroxy-quinolinato) aluminum (Tris (8-hydroxy-quinolinato) aluminum; Alq ₃ ) was deposited to a thickness of 200 Å as an electron transport layer. I did.

Then, lithium fluoride (LiF) was deposited to a thickness of 10 Å as an electron injection layer. Then, an Al cathode was deposited to a thickness of 1000Å to produce an OLED.

On the other hand, all organic compounds required for OLED device fabrication were vacuum-sublimated and purified under 10 ^-6 ~10 ^-8 torr for each material, and used for OLED fabrication.

[Example]

In addition to using the materials in Table 4 corresponding to the green light emitting layer in the comparative example in place of CBP, the other materials were used in the same manner as in the comparative example to fabricate a device.

Test example: OLED Device characteristic evaluation

Table 4 shows the driving voltage, efficiency, and lifetime of the OLED devices manufactured in Examples and Comparative Examples at 1000 cd/m2 and when the efficiency is 50%.

Example No. Compound No. Driving voltage (Op.V) Efficiency (Cd/A) Life (T50) Comparative example Ref 6.72 35.1 220 One One 4.9 47.8 350 2 2 4.91 48.9 360 3 3 4.9 49.8 340 4 4 4.83 50.1 380 5 7 4.85 49.5 330 6 9 4.83 50.2 300 7 11 4.78 52.1 300 8 13 4.83 45.9 380 9 14 4.89 48.6 400 10 17 4.79 51.3 360 11 20 4.78 51 360 12 23 4.87 47 420 13 26 4.87 47.6 430 14 28 4.92 46.2 420 15 30 4.83 49.9 390 16 32 4.81 50.5 400 17 33 5.05 46.3 400 18 34 4.98 47.8 430 19 36 5.01 47.2 410 20 38 5.08 45.9 410 21 39 4.98 48 390 22 42 4.85 49.7 390 23 51 4.82 51.8 410 24 43 4.9 50.7 420 25 44 4.91 51.1 400 26 45 4.9 51.4 420 27 46 4.83 52.3 430 28 50 4.81 52 420 29 53 4.79 53.1 400 30 55 4.88 50.5 450 31 58 4.9 51.8 470 32 59 4.81 52.9 420 33 60 4.85 49.8 450 34 62 4.82 52.8 410 35 64 4.78 53.2 420 36 65 4.89 50.1 460 37 67 4.85 50.9 450 38 70 4.94 49.5 480 39 72 4.81 51.6 430 40 74 4.81 51.9 460 41 75 4.99 49.2 470 42 76 4.96 50 480 43 81 4.91 50.2 460 44 84 4.84 51 460

100 substrates
200 anode
300 organic matter layer
301 hole injection layer
302 hole transport layer
303 emitting layer
304 Hole Reservoir
305 electron transport layer
306 Electron injection layer
400 cathode

Claims (13)

Compounds of Formula 1:
[Formula 1]

In Formula 1,
R ₁ to R ₉ are the same as or different from each other, and each independently hydrogen; halogen; C ₁ to C ₆₀ linear or branched substituted or unsubstituted alkyl; C ₂ to C ₆₀ straight or branched substituted or unsubstituted alkenyl; C ₂ to C ₆₀ straight or branched substituted or unsubstituted alkynyl; C ₁ to C ₆₀ linear or branched substituted or unsubstituted alkoxy; C ₆ to C ₆₀ linear or branched substituted or unsubstituted aryloxy; C ₃ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted cycloalkyl; C ₂ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted heterocycloalkyl; C ₆ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted aryl; C ₂ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted heterocyclic group; A substituted or unsubstituted C ₁₀ to C ₆₀ spiro group; C ₁ to C ₂₀ substituted or unsubstituted alkylamine; C ₆ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted arylamine; And C ₂ to C ₆₀ is selected from the group consisting of monocyclic or polycyclic substituted or unsubstituted heteroarylamine, these may further form a ring with an adjacent substituent. The method according to claim 1, R ₁ is C ₆ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted aryl; C ₂ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted heterocyclic group; Or a substituted or unsubstituted C ₁₀ to C ₆₀ spiro group. The compound of claim 1, wherein Formula 1 is represented by the following Formula 2:
[Formula 2]

In Formula 2,
R ₂ to R ₉ are as defined in Formula 1,
L is a C ₆ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted arylene; Or C ₂ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted heteroarylene,
Ar is C ₆ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted aryl; Or C ₂ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted heterocyclic group,
m is an integer from 0 to 3, n is an integer from 1 to 3,
When m is 2 or more, L is the same as or different from each other, and when n is 2 or more, Ar is the same or different from each other. The compound of claim 3, wherein L is substituted or unsubstituted, and is a tricyclic or less arylene or a tricyclic or less heteroarylene. The compound of claim 3, wherein L is substituted or unsubstituted, and is phenylene or monocyclic heteroarylene. The compound of claim 3, wherein L is a substituted or unsubstituted phenylene, a substituted or unsubstituted naphthylene, or a substituted or unsubstituted anthrylene. The compound of claim 3, wherein L is phenylene. The method according to claim 3, Ar is C ₆ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted aryl; Or a C ₂ to C ₆₀ monocyclic or polycyclic substituted or unsubstituted N-containing heterocyclic group. The method of claim 3, wherein Ar is substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthryl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted triphenylenyl, substituted or Compounds that are unsubstituted pyridyl, substituted or unsubstituted pyrimidyl, substituted or unsubstituted triazinyl, substituted or unsubstituted quinolyl, or substituted or unsubstituted isoquinolyl. An organic light-emitting device comprising an anode, a cathode, and at least one organic material layer provided between the anode and the cathode, and at least one of the organic material layers comprises the compound of any one of claims 1 to 9. The organic light-emitting device of claim 10, wherein the organic material layer containing the compound is at least one layer selected from a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer. The organic light-emitting device of claim 10, wherein the organic material layer containing the compound is an emission layer. The organic light-emitting device of claim 10, wherein the organic material layer including the compound is an electron transport layer.

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