KR20220098455A - An electroluminescent compound and an electroluminescent device comprising the same - Google Patents

Abstract

The present invention relates to a novel organic light emitting compound represented by chemical formula I, which is adopted to an organic layer such as an electron transport layer in an organic light emitting element and a light efficiency improving layer (capping layer) provided in the organic light emitting element to implement light emitting properties such as low voltage driving and excellent light emitting efficiency; and an organic light emitting element including the same.

Description

An organic light emitting compound and an organic light emitting device comprising the same

The present invention relates to an organic light emitting compound, and more particularly, an organic light emitting compound characterized in that it is employed as an organic layer in an organic light emitting device, and a light efficiency improvement layer (Capping layer) material provided in the organic light emitting device, and a device using the same It relates to an organic light-emitting device with significantly improved light-emitting characteristics such as low-voltage driving and excellent light-emitting efficiency.

The organic light emitting device can be formed on a transparent substrate as well as being able to drive at a low voltage of 10 V or less compared to a plasma display panel or an inorganic electroluminescence (EL) display, and consume relatively little power. , has the advantage of excellent color, and can represent three colors of green, blue, and red, and has recently become a subject of much interest as a next-generation display device.

However, in order for such an organic light emitting device to exhibit the above characteristics, a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, etc. However, the development of a stable and efficient organic layer material for an organic light emitting device has not yet been sufficiently developed.

Therefore, in order to realize a more stable organic light emitting device, and to achieve high efficiency, long lifespan, and large size of the device, additional improvements are required in terms of efficiency and lifespan characteristics. It is desperately needed.

In addition, in recent years, research on improving the characteristics of an organic light emitting device by giving a change in the performance of each organic layer material, as well as a technology for improving color purity and increasing luminous efficiency by an optical thickness optimized between an anode and a cathode has been developed. It has been focused on one of the important factors for improving the performance, and as an example of this method, an increase in light efficiency and excellent color purity are achieved by using a capping layer on an electrode.

Therefore, the present invention is a novel organic light emitting compound that can implement excellent light emitting characteristics such as low voltage driving and improved light emitting efficiency of the device by being employed in an organic layer in an organic light emitting device or a light efficiency improving layer (Capping layer) provided in the organic light emitting device and An object of the present invention is to provide an organic light emitting device including the same.

The present invention provides an organic light emitting compound represented by the following [Formula I] in order to solve the above problems.

[Formula Ⅰ]

The characteristic structure of the [Formula I] and the compounds implemented thereby, Z, X, L ₁ to L ₃ , Ar ₁ and R ₁ to R ₄ will be described later.

When the organic light emitting compound according to the present invention is employed as an organic layer in an organic light emitting device or as a material for a light efficiency improvement layer provided in an organic light emitting device, it is possible to realize light emitting characteristics such as low voltage driving and excellent luminous efficiency of the device, so it is useful for various display devices can be used

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

The present invention relates to an organic light-emitting compound represented by the following [Formula I], which can achieve light-emitting characteristics such as low voltage driving of the organic light-emitting device and excellent light-emitting efficiency.

The compound represented by [Formula I] according to the present invention structurally introduces benzoxazole and/or benzothiazole derivatives at the 1st and 3rd carbon positions of isoindole, and aryl at the -N terminal of isoindole. It is characterized in that a characteristic structure such as a group or a heteroaryl group is introduced, and the low voltage driving characteristic and the luminous efficiency characteristic of the organic light emitting diode can be improved through these structural characteristics.

[Formula Ⅰ]

In the above [Formula I],

Z is each O or S, and the plurality of Zs are the same as or different from each other.

X is each independently N or CR, a plurality of R are the same as or different from each other, and each R is independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or An unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, or a substituted or unsubstituted halogenated alkyl group having 1 to 20 carbon atoms , substituted or unsubstituted halogenated alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted aryl group having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, substituted or unsubstituted carbon number 1 to 20 alkylsilyl group and a substituted or unsubstituted C6-C30 arylsilyl group.

In addition, the plurality of R may be bonded to each other or connected to an adjacent substituent to form an aromatic monocyclic or polycyclic ring.

L ₁ to L ₃ are each independently a single bond, or is selected from a substituted or unsubstituted arylene group having 6 to 30 carbon atoms and a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, and n, m and o are each It is independently an integer of 0 to 2, and when n, m, and o are each 2, a plurality of L ₁ to L ₃ are the same as or different from each other, respectively.

Ar ₁ is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylamine group having 1 to 30 carbon atoms, and a substituted or unsubstituted carbon number It is selected from an arylamine group of 6 to 50, p is an integer of 1 to 3, and when p is 2 or more, a plurality of Ar ₁ are the same as or different from each other.

According to an embodiment of the present invention, Ar ₁ may be benzoxazole or a benzothiazole derivative that can be identified in the skeleton structure.

R ₁ to R ₄ are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted C 1 to C 20 alkyl group, a substituted or unsubstituted C 2 to C 20 alkenyl group, a substituted or unsubstituted C 3 to 20 cycloalkyl group, substituted or unsubstituted C1-C20 alkoxy group, substituted or unsubstituted C1-C20 halogenated alkyl group, substituted or unsubstituted C1-C20 halogenated alkoxy group, substituted or an unsubstituted C6-C30 aryl group and a substituted or unsubstituted C3-C30 heteroaryl group.

In addition, R ₁ to R ₄ may be bonded to each other or connected to an adjacent substituent to form an aromatic monocyclic or polycyclic ring.

Meanwhile, in the definitions of R, L ₁ to L ₃ , Ar ₁ and R ₁ to R ₄ , 'substituted or unsubstituted' means deuterium, a halogen group, a cyano group, a nitro group, a hydroxyl group, a silyl group, an alkyl group, From the group consisting of a halogenated alkyl group, a deuterated alkyl group, a cycloalkyl group, a heterocycloalkyl group, an alkoxy group, a halogenated alkoxy group, a deuterated alkoxy group, an aryl group, a heteroaryl group, an alkylamine group, an arylamine group and a silyl group. It means that it is substituted with one or more selected substituents, or is substituted with a substituent to which two or more of the substituents are connected, or does not have any substituents.

For specific examples, the substituted aryl group means that a phenyl group, a biphenyl group, a naphthalene group, a fluorenyl group, a pyrenyl group, a phenanthrenyl group, a perylene group, a tetracenyl group, an anthracenyl group, etc. are substituted with other substituents do.

In addition, the substituted heteroaryl group refers to a pyridyl group, a thiophenyl group, a triazine group, a quinoline group, a phenanthroline group, an imidazole group, a thiazole group, an oxazole group, a carbazole group and a condensed heterocyclic group thereof, such as a benzquinoline group. , a benzimidazole group, a benzoxazole group, a benzthiazole group, a benzcarbazole group, a dibenzothiophenyl group, a dibenzofuran group, and the like are substituted with other substituents.

In the present invention, examples of the substituents will be described in detail below, but the present invention is not limited thereto.

In the present invention, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 20. Specific examples include methyl group, ethyl group, propyl group, n-propyl group, isopropyl group, butyl group, n-butyl group, isobutyl group, tert-butyl group, sec-butyl group, 1-methyl-butyl group, 1- Ethyl-butyl group, pentyl group, n-pentyl group, isopentyl group, neopentyl group, tert-pentyl group, hexyl group, n-hexyl group, 1-methylpentyl group, 2-methylpentyl group, 4-methyl- 2-pentyl group, 3,3-dimethylbutyl group, 2-ethylbutyl group, heptyl group, n-heptyl group, 1-methylhexyl group, cyclopentylmethyl group, cyclohexylmethyl group, octyl group, n-octyl group, tert -Octyl group, 1-methylheptyl group, 2-ethylhexyl group, 2-propylpentyl group, n-nonyl group, 2,2-dimethylheptyl group, 1-ethyl-propyl group, 1,1-dimethyl-propyl group , isohexyl group, 2-methylpentyl group, 4-methylhexyl group, 5-methylhexyl group, and the like, but is not limited thereto.

In the present invention, the alkoxy group may be straight-chain or branched. Although the number of carbon atoms of the alkoxy group is not particularly limited, it is preferably 1 to 20, which is a range that does not cause steric hindrance. Specifically, methoxy group, ethoxy group, n-propoxy group, isopropoxy group, i-propyloxy group, n-butoxy group, isobutoxy group, tert-butoxy group, sec-butoxy group, n-pentyloxy group , neopentyloxy group, isopentyloxy group, n-hexyloxy group, 3,3-dimethylbutyloxy group, 2-ethylbutyloxy group, n-octyloxy group, n-nonyloxy group, n-decyloxy group , a benzyloxy group, a p-methylbenzyloxy group, etc., but is not limited thereto.

In the present invention, a deuterated alkyl group or alkoxy group, halogenated alkyl group or alkoxy group means an alkyl group or alkoxy group in which the alkyl group or alkoxy group is substituted with deuterium or a halogen group.

In the present invention, the aryl group may be monocyclic or polycyclic, and the number of carbon atoms is not particularly limited, but is preferably 6 to 30. Examples of the monocyclic aryl group include a phenyl group, a biphenyl group, a terphenyl group, and a stilbene group, and examples of the polycyclic aryl group include a naphthyl group, anthracenyl group, phenanthrenyl group, pyrenyl group, perylenyl group, tetracenyl group. , chrysenyl group, fluorenyl group, acenaphthacenyl group, triphenylene group, fluoranthrene group, etc., but the scope of the present invention is not limited to these examples.

,

,

등이 있다.In the present invention, the fluorenyl group is a structure in which two ring organic compounds are connected through one atom, for example,

,

,

etc.

,

등이 있다.In the present invention, the fluorenyl group includes a structure of an open fluorenyl group, wherein the open fluorenyl group is a structure in which one ring compound is disconnected in a structure in which two ring organic compounds are connected through one atom. , for example

,

etc.

,

,

,

등이 있다.In addition, the carbon atom of the ring may be substituted with any one or more heteroatoms selected from N, S and O, for example,

,

,

,

etc.

In the present invention, the heteroaryl group is a heterocyclic group containing O, N or S as a heteroatom, and the number of carbon atoms is not particularly limited, but preferably has 2 to 30 carbon atoms, and a specific example thereof in the present invention is a thiophene group , furan group, pyrrole group, imidazole group, thiazole group, oxazole group, oxadiazole group, triazole group, pyridyl group, bipyridyl group, pyrimidyl group, triazine group, triazole group, acridyl group, pyridazine group, pyra Zinyl group, quinolinyl group, quinazoline group, quinoxalinyl group, phthalazinyl group, pyrido pyrimidinyl group, pyrido pyrazinyl group, pyrazino pyrazinyl group, isoquinoline group, indole group, carbazole group, benzoxa Zol group, benzoimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group, dibenzofuranyl group, phenanthroline group, thiazolyl group, isoxazolyl group, oxadia and a zolyl group, a thiadiazolyl group, a benzothiazolyl group, a phenothiazinyl group, a phenoxazine group, a phenothiazine group, and the like, but are not limited thereto.

In the present invention, the silyl group is an unsubstituted silyl group or a silyl group substituted with an alkyl group, an aryl group, etc., and specific examples of the silyl group include trimethylsilyl, triethylsilyl, triphenylsilyl, trimethoxysilyl, dimethoxy phenylsilyl, diphenylmethylsilyl, diphenylvinylsilyl, methylcyclobutylsilyl, dimethylfurylsilyl, and the like, but is not limited thereto.

In the present invention, the amine group may be -NH ₂ , an alkylamine group, an arylamine group, etc., the arylamine group means an amine substituted with an aryl, the alkylamine group means an amine substituted with an alkyl, and an arylamine group Examples of these include a substituted or unsubstituted monoarylamine group, a substituted or unsubstituted diarylamine group, or a substituted or unsubstituted triarylamine group, and the aryl group in the arylamine group is the same as the definition of the aryl group, , The alkyl group of the alkylamine group is also the same as the definition of the alkyl group.

Specific examples of the halogen group as a substituent used in the present invention include fluorine (F), chlorine (Cl), bromine (Br), and the like.

In the present invention, the cycloalkyl group refers to, and includes, monocyclic, polycyclic and spiro alkyl radicals, preferably containing 3 to 20 ring carbon atoms, cyclopropyl, cyclopentyl, cyclohexyl, bicyclo heptyl, spirodecyl, spirodecyl, adamantyl, and the like, wherein the cycloalkyl group may be optionally substituted.

In the present invention, heterocycloalkyl groups refer to and include aromatic and non-aromatic cyclic radicals containing one or more heteroatoms, wherein one or more heteroatoms are O, S, N, P, B, Si, and Se , Preferably it is selected from O, N, or S, and specifically, when N is included, it may be aziridine, pyrrolidine, piperidine, azepane, azocan, and the like.

The organic light emitting compound according to the present invention represented by the above [Formula I] can be used in various organic layers including the electron transport layer in the organic light emitting device due to its structural specificity, and also as a light efficiency improving layer material provided in the organic light emitting device. can be used

Preferred examples of the organic light emitting compound represented by [Formula I] according to the present invention include the following compounds, but are not limited thereto.

As such, the organic light emitting compound according to the present invention can synthesize an organic light emitting compound having various characteristics by using a characteristic skeleton exhibiting intrinsic properties and a moiety having intrinsic properties introduced thereto, As a result, the organic light emitting compound according to the present invention can be applied to various organic layer materials such as a light emitting layer, a hole transport layer, an electron transport layer, an electron blocking layer, and a hole blocking layer. can be further improved, and also when employed in a light efficiency improving layer provided in an organic light emitting device, it is possible to improve light emitting characteristics such as light emitting efficiency.

In addition, the compound of the present invention can be applied to a device according to a general organic light emitting device manufacturing method.

The organic light emitting device according to an embodiment of the present invention may have a structure including a first electrode and a second electrode and an organic layer disposed therebetween. Except that, it may be manufactured using conventional device manufacturing methods and materials.

The organic layer of the organic light emitting diode according to the present invention may have a single layer structure, but may have a multilayer structure in which two or more organic layers are stacked. For example, it may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, an electron blocking layer, a hole blocking layer, a light efficiency improving layer (Capping layer), and the like. However, the present invention is not limited thereto and may include a smaller number or a larger number of organic layers.

In addition, the organic electroluminescent device according to an embodiment of the present invention includes a substrate, a first electrode (anode), an organic layer, a second electrode (cathode) and a light efficiency improving layer, wherein the light efficiency improving layer is a lower portion of the first electrode ( Bottom emission) or on the second electrode top (Top emission).

In the method of forming the second electrode on top (Top emission), the light formed in the light emitting layer is emitted toward the cathode, and the light emitted toward the cathode passes through the light efficiency improvement layer (CPL) formed of the compound according to the present invention having a relatively high refractive index. The wavelength of is amplified and thus the light efficiency is increased .

The organic layer structure of the preferred organic light emitting device according to the present invention will be described in more detail in the following Examples.

In addition, the organic light emitting diode according to the present invention is a metal or conductive metal oxide or an alloy thereof on a substrate by using a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation. It can be prepared by depositing an anode, forming an organic layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer thereon, and then depositing a material that can be used as a cathode thereon.

In addition to this method, an organic light emitting diode may be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate. The organic layer may have a multilayer structure including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer, but is not limited thereto and may have a single layer structure. In addition, the organic layer can be formed in a smaller number by a solvent process rather than a deposition method using various polymer materials, such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer method. It can be made in layers.

As the anode material, a material having a large work function is generally preferred so that holes can be smoothly injected into the organic layer. Specific examples of the anode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, gold, or alloys thereof, zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO), etc. Metal oxides, combinations of metals and oxides such as ZnO:Al or SnO ₂ :Sb, poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT) , a conductive polymer such as polypyrrole and polyaniline, but is not limited thereto.

The cathode material is preferably a material having a small work function to facilitate electron injection into the organic layer. Specific examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or alloys thereof, and multilayers such as LiF/Al or LiO ₂ /Al Structural materials and the like, but are not limited thereto.

The hole injection material is a material capable of well injecting holes from the anode at a low voltage, and it is preferable that the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of the hole injection material include metal porphyrine, oligothiophene, arylamine-based organic material, hexanitrile hexaazatriphenylene, quinacridone-based organic material, perylene-based organic material, anthraquinone, polyaniline, and polythiophene-based conductive polymers, but are not limited thereto.

As the hole transport material, a material capable of transporting holes from the anode or the hole injection layer to the light emitting layer is suitable, and a material having high hole mobility is suitable. Specific examples include an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion together. can be further improved.

The light emitting material is a material capable of emitting light in the visible ray region by receiving and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency for fluorescence or phosphorescence is preferable. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq ₃ ), carbazole-based compounds, dimerized styryl compounds, BAlq, 10-hydroxybenzoquinoline-metal compounds, benzoxazole, benzthiazole and There are benzimidazole-based compounds, poly(p-phenylenevinylene) (PPV)-based polymers, spiro compounds, polyfluorene, rubrene, and the like, but is not limited thereto.

As the electron transport material, a material capable of receiving electrons from the cathode and transferring them to the light emitting layer is suitable, and a material having high electron mobility is suitable, and may be a compound represented by [Formula I] according to the present invention, and Examples include, but are not limited to, an Al complex of 8-hydroxyquinoline, a complex including Alq ₃ , an organic radical compound, and a hydroxyflavone-metal complex.

The organic light emitting diode according to the present invention may be a top emission type, a back emission type, or a double-sided emission type depending on the material used.

In addition, the organic light emitting compound according to the present invention may act on a principle similar to that applied to the organic light emitting device in organic electronic devices including organic solar cells, organic photoreceptors, organic transistors, and the like.

Hereinafter, the present invention will be described in more detail with reference to preferred embodiments. However, these examples are for explaining the present invention in more detail, the scope of the present invention is not limited thereby, and it is common in the art that various changes and modifications are possible within the scope and spirit of the present invention. It will be self-evident to those with knowledge.

Synthesis example 1: Synthesis of compound 4

(One) production example 1: Synthesis of Intermediate 4-1

2H-isoindole (10 g, 0.085 mol), 4-Iodobiphenyl (28.7 g, 0.102 mol), Cs ₂ CO ₃ (55.6 g, 0.171 mol), Cu(OAc) ₂ H ₂ O (0.17 g, 0.001 mol), DMF was added and the reaction was stirred at 110 °C for 24 hours. After the reaction was completed, 17.2 g (yield 74.8%) of <Intermediate 4-1> was obtained by extraction, concentration, and column.

(2) production example 2: Synthesis of Intermediate 4-1

Intermediate 4-1 (10 g, 0.037 mol) and N-Bromosuccinimide (15.9 g, 0.089 mol) were added to 200 mL of DMF and reacted by stirring at room temperature for 5 hours. After completion of the reaction, extraction and concentration were performed, followed by column and recrystallization to obtain 9.5 g (yield 59.9%) of <Intermediate 4-2>.

(3) production example 3: Synthesis of compound 4

Intermediate 4-2 (10.0 g, 0.023 mol), Benzoxazole (8.4 g, 0.070 mol), Pd(OAc) ₂ (0.1 g, 0.5 mmol), Cu(OAc) ₂ (0.2 g, 0.9 mmol), K ₂ CO Toluene was added to ₃ (12.9 g, 0.094 mol), PPh ₃ (6.1 g, 0.23 mol), and the reaction was stirred under reflux at 110° C. for 4 hours. After completion of the reaction, 8.5 g (yield 72.1%) of <Compound 4> was obtained by extraction and concentration, followed by column and recrystallization.

LC/MS: m/z=503[(M+1) ⁺ ]

Synthesis example 2: Synthesis of compound 13

(One) production example 1: Synthesis of Intermediate 13-1

2H-isoindole (10 g, 0.085 mol) and N-Bromosuccinimide (36.5 g, 0.205 mol) were added to 300 mL of DMF and reacted by stirring at room temperature for 5 hours. After completion of the reaction, extraction and concentration were performed, followed by column and recrystallization to obtain 12.5 g (yield 53.3%) of <Intermediate 13-1>.

(2) production example 2: Synthesis of intermediate 13-2

Intermediate 13-1 (10.0 g, 0.036 mol), Benzoxazole (13.0 g, 0.109 mol), Pd(OAc) ₂ (0.2 g, 0.7 mmol), Cu(OAc) ₂ (0.3 g, 0.002 mol), K ₂ CO Toluene was added to ₃ (20.1 g, 0.146 mol), PPh ₃ (9.5 g, 0.036 mol), and the reaction was stirred under reflux at 110° C. for 4 hours. After completion of the reaction, 8.7 g (yield 68.1%) of <Intermediate 13-2> was obtained by extraction and concentration, followed by column and recrystallization.

(3) production example 3: Synthesis of compound 13'

Intermediate 13-2 (10 g, 0.029 mol), 9-(4-Iodophenyl)carbazole (12.6 g, 0.034 mol), Cs ₂ CO ₃ (18.6 g, 0.057 mol), Cu(OAc) ₂ H ₂ O (0.06 g, 0.0003 mol), DMF was added, and the reaction was stirred at 110 °C for 24 hours. After completion of the reaction, the mixture was extracted, concentrated, and columned to obtain 12.2 g (yield 72.3%) of <Compound 13>.

LC/MS: m/z=592[(M+1) ⁺ ]

Synthesis example 3: Synthesis of compound 57

(One) production example 1: Synthesis of intermediate 57-1

2H-isoindole (10 g, 0.085 mol), 2-(4-Iodophenyl)benzoxazole (32.9 g, 0.102 mol), Cs ₂ CO ₃ (55.6 g, 0.171 mol), Cu(OAc) ₂ H ₂ O (0.17 g , 0.001 mol), DMF was added, and the reaction was stirred at 110 °C for 24 hours. After completion of the reaction, the mixture was extracted, concentrated, and columned to obtain 18.3 g (yield: 69.1%) of <Intermediate 57-1>.

(2) production example 2: Synthesis of intermediate 57-2

Intermediate 57-1 (10 g, 0.032 mol) and N-Bromosuccinimide (13.8 g, 0.077 mol) were added to 200 mL of DMF and reacted by stirring at room temperature for 5 hours. After completion of the reaction, extraction and concentration were performed, followed by column and recrystallization to obtain 9.1 g (yield 60.3%) of <Intermediate 57-2>.

(3) production example 3: Synthesis of compound 57

Intermediate 57-2 (10.0 g, 0.021 mol), 4-(2-benzo[d]oxazolyl)phenylboronic acid (12.3 g, 0.051 mol), K ₂ CO ₃ (17.7 g, 0.128 mol), Pd(PPh3)4 (0.5 g, 0.0004 mol), toluene 200 mL, ethanol 50 mL, H ₂ O 50 mL were added, and the reaction was stirred under reflux at 100 °C for 6 hours. After completion of the reaction, 10.5 g (yield 70.6%) of <Compound 57> was obtained by extraction, recrystallization and column purification.

LC/MS: m/z=696[(M+1) ⁺ ]

Synthesis example 4: Synthesis of compound 181

(One) production example 1: Synthesis of intermediate 181-1

Intermediate 13-1 (10.0 g, 0.036 mol), Benzothiazole (14.8 g, 0.109 mol), Pd(OAc) ₂ (0.16 g, 0.7 mmol), Cu(OAc) ₂ (0.3 g, 0.002 mol), K ₂ CO Toluene was added to ₃ (20.1 g, 0.146 mol), PPh ₃ (9.5 g, 0.036 mol), and the reaction was stirred under reflux at 110° C. for 4 hours. After completion of the reaction, 9.1 g (yield 65.2%) of <Intermediate 181-1> was obtained by extraction and concentration, followed by column and recrystallization.

(2) production example 2: Synthesis of compound 181

Intermediate 181-1 (10 g, 0.026 mol), 4-(Diphenylamino)iodobenzene (11.6 g, 0.031 mol), Cs ₂ CO ₃ (16.9 g, 0.052 mol), Cu(OAc) ₂ H ₂ O (0.05 g, 0.003 mol), DMF was added, and the reaction was stirred at 110 °C for 24 hours. After completion of the reaction, the mixture was extracted, concentrated, and columned to obtain 10.8 g (yield 66.1%) of <Compound 181>.

LC/MS: m/z=626[(M+1) ⁺ ]

Synthesis example 5: Synthesis of compound 216

(One) production example 1: Synthesis of compound 216

Intermediate 57-2 (10.0 g, 0.021 mol), Benzothiazole (8.7 g, 0.064 mol), Pd(OAc) ₂ (0.1 g, 0.4 mmol), Cu(OAc) ₂ (0.2 g, 0.9 mmol), K ₂ CO Toluene was added to ₃ (11.8 g, 0.085 mol) and PPh ₃ (5.6 g, 0.021 mol), and the reaction was stirred under reflux at 110° C. for 4 hours. After completion of the reaction, 6.2 g (yield 50.3%) of <Compound 216> was obtained by extraction and concentration, followed by column and recrystallization.

LC/MS: m/z=576[(M+1) ⁺ ]

Device embodiment (capping layer)

In an embodiment according to the present invention, the ITO transparent electrode was cleaned after patterning so that the light emitting area has a size of 2 mm × 2 mm using an ITO glass substrate containing Ag of 25 mm × 25 mm × 0.7 mm. After the substrate was mounted in a vacuum chamber, the base pressure was 1 × 10 ^-6 torr or more, and the organic material and the metal were deposited on the Ag-containing ITO glass substrate in the following structure.

Device Examples 1 to 15

By employing the compound implemented according to the present invention in the light efficiency improving layer, an organic light emitting device having the following device structure was manufactured, and light emission characteristics including light emission efficiency were measured.

Ag/ITO / hole injection layer (HAT-CN, 5 nm) / hole transport layer (α-NPB, 100 nm) / electron blocking layer (TCTA, 10 nm) / light emitting layer (20 nm) / electron transport layer (201: Liq, 30 nm) / LiF (1 nm) / Mg:Ag (15 nm) / Light efficiency improvement layer (70 nm)

HAT-CN was formed to a thickness of 5 nm to form a hole injection layer on an ITO transparent electrode containing Ag on a glass substrate, and then α-NPB was formed into a film of 100 nm for the hole transport layer. The electron blocking layer was formed of TCTA with a thickness of 10 nm. In addition, the light emitting layer was co-deposited at 20 nm using BH1 as a host compound and BD1 as a dopant compound. In addition, an electron transport layer (the following [201] compound Liq 50% doped) was formed to a thickness of 30 nm and LiF 1 nm. Then, 15 nm of Mg:Ag was formed at a ratio of 1:9. And as a light efficiency improving layer (capping layer) compound, compounds 1, 4, 5, 13, 22, 33, 35, 57, 99, 111, 120, 136, 181, 183, 216 embodied in the present invention at 70 nm By forming a film to a thickness, an organic light emitting device was manufactured.

Device Comparative Example 1

The organic light emitting device for Device Comparative Example 1 was manufactured in the same manner except that the light efficiency improving layer was not used in the device structures of Examples 1 to 15.

Device Comparative Example 2

The organic light emitting device for Device Comparative Example 2 was prepared in the same manner except that Alq ₃ was used instead of the compound of the present invention as the light efficiency improving layer compound in the device structures of Examples 1 to 15.

Experimental Example 1: Light emitting properties of Device Examples 1 to 15

The organic light emitting device manufactured according to the above example was measured using a source meter (Model 237, Keithley) and a luminance meter (PR-650, Photo Research) to measure driving voltage, current efficiency, and color coordinates, and the result value based on 1,000 nits is shown in [Table 1] below.

Example Light Efficiency Improvement Layer V cd/A CIEx CIEy One Formula 1 3.9 8.0 0.139 0.046 2 Formula 4 3.8 8.3 0.131 0.052 3 Formula 5 3.5 8.8 0.132 0.058 4 Formula 13 3.9 8.4 0.133 0.056 5 Formula 22 3.8 8.2 0.135 0.049 6 Formula 33 3.7 8.5 0.131 0.057 7 Formula 35 3.8 8.3 0.130 0.055 8 chemical formula 57 3.7 8.5 0.131 0.054 9 Formula 99 3.8 8.2 0.136 0.050 10 Formula 111 3.8 8.2 0.130 0.053 11 Formula 120 3.9 8.1 0.135 0.051 12 Formula 136 3.5 8.7 0.138 0.047 13 Formula 181 3.6 8.5 0.131 0.057 14 Formula 183 3.7 8.6 0.130 0.054 15 Formula 216 3.8 8.3 0.133 0.052 Comparative Example 1 not used 4.6 7.0 0.150 0.141 Comparative Example 2 Alq ₃ 4.3 7.8 0.147 0.058

Looking at the results shown in [Table 1], when the compound according to the present invention is applied to the light efficiency improving layer provided in the organic light emitting device, the conventional device without the light efficiency improving layer and the compound used in the conventional light efficiency improving layer are employed. It can be seen that the driving voltage is reduced and the current efficiency is improved compared to the devices (Comparative Examples 1 and 2).

[HAT-CN] [α-NPB] [BH1] [BD1] [201]

[TCTA]

Claims (8)

An organic light emitting compound represented by the following [Formula I]:
[Formula Ⅰ]

In the [Formula I],
Z is each O or S, the plurality of Z are the same or different from each other,
Each X is independently N or CR, a plurality of R are the same or different from each other, and each R is independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted C 1 to C 20 alkyl group, a substituted or An unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, or a substituted or unsubstituted halogenated alkyl group having 1 to 20 carbon atoms , a substituted or unsubstituted halogenated alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted carbon number 1 to 20 alkylsilyl groups and substituted or unsubstituted C6 to C30 arylsilyl groups,
The plurality of R may be bonded to each other or connected to an adjacent substituent to form an aromatic monocyclic or polycyclic ring,
L ₁ to L ₃ are each independently a single bond, or is selected from a substituted or unsubstituted arylene group having 6 to 30 carbon atoms and a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, and n, m and o are each It is independently an integer of 0 to 2, and when n, m and o are each 2, a plurality of L ₁ to L ₃ are the same as or different from each other,
Ar ₁ is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylamine group having 1 to 30 carbon atoms, and a substituted or unsubstituted carbon number It is selected from an arylamine group of 6 to 50, p is an integer of 1 to 3, and when p is 2 or more, a plurality of Ar ₁ are the same as or different from each other,
R ₁ to R ₄ are each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted C 1 to C 20 alkyl group, a substituted or unsubstituted C 2 to C 20 alkenyl group, a substituted or unsubstituted C number 3 to 20 cycloalkyl group, substituted or unsubstituted C1-C20 alkoxy group, substituted or unsubstituted C1-C20 halogenated alkyl group, substituted or unsubstituted C1-C20 halogenated alkoxy group, substituted or an unsubstituted C 6 to C 30 aryl group and a substituted or unsubstituted C 3 to C 30 heteroaryl group,
The R ₁ to R ₄ may be bonded to each other or connected to an adjacent substituent to form an aromatic monocyclic or polycyclic ring. According to claim 1,
In the definitions of R, L ₁ to L ₃ , Ar ₁ and R ₁ to R ₄ , 'substituted or unsubstituted' means deuterium, a halogen group, a cyano group, a nitro group, a hydroxyl group, a silyl group, an alkyl group, a halogenated selected from the group consisting of an alkyl group, a deuterated alkyl group, a cycloalkyl group, a heterocycloalkyl group, an alkoxy group, a halogenated alkoxy group, a deuterated alkoxy group, an aryl group, a heteroaryl group, an alkylamine group, an arylamine group and a silyl group. An organic light-emitting compound, characterized in that it is substituted with one or two or more substituents, or is substituted with a substituent to which two or more of the substituents are connected, or does not have any substituents. According to claim 1,
The [Formula I] is an organic light emitting compound, characterized in that any one selected from the following [Compound 1] to [Compound 231]:

An organic light emitting device comprising a first electrode, a second electrode, and at least one organic layer disposed between the first electrode and the second electrode,
At least one of the organic layers is an organic light emitting device comprising the organic light emitting compound of [Formula I] according to claim 1. 5. The method of claim 4,
The organic layer is selected from a hole injection layer, a hole transport layer, a layer that performs both hole injection and hole transport functions, an electron transport layer, an electron injection layer, a layer that performs both electron transport and electron injection functions, an electron blocking layer, a hole blocking layer, and a light emitting layer including one or more floors that become
At least one of the layers comprises an organic light emitting compound represented by the [Formula I]. 6. The method of claim 5,
An organic light emitting device comprising an organic light emitting compound represented by the above [Formula I] in any one of the electron transport layer, the electron injection layer, and the layer performing both electron transport and electron injection functions. 5. The method of claim 4,
Further comprising a light efficiency improvement layer (Capping layer) formed on at least one side opposite to the organic layer among the upper or lower portions of the first electrode and the second electrode,
The light efficiency improving layer is an organic light emitting device, characterized in that it comprises an organic light emitting compound represented by the [Formula I]. 8. The method of claim 7,
The light efficiency improving layer is an organic light emitting device, characterized in that formed on at least one of a lower portion of the first electrode or an upper portion of the second electrode.