KR102233636B1 - Compound and organic light emitting device comprising the same - Google Patents

Abstract

The present specification provides a compound of Formula 1 and an organic light emitting device including the same.

Description

A compound and an organic light-emitting device comprising the same TECHNICAL FIELD

The present specification relates to a compound and an organic light emitting device including the same.

This specification claims the benefit of the filing date of the Korean Patent Application No. 10-2018-0020323 filed with the Korean Intellectual Property Office on February 21, 2018, the contents of which are all incorporated herein.

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 as needed. For example, as the organic thin film material, a compound capable of constituting an emission layer by itself may be used, or a compound capable of serving as a host or a dopant of the host-dopant-based emission 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.

International Patent Application Publication No. 2003-012890

The present specification provides a compound and an organic light emitting device including the same.

An exemplary embodiment of the present specification provides a compound represented by Formula 1 below.

[Formula 1]

In Formula 1,

Ar1 to Ar4 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group,

X1 is S; O; SO ₂ ; Or CRR',

X2 is a direct bond; O; S; Or CR"R"',

R and R'are the same as or different from each other and each independently a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, and R and R'are bonded to each other to include a substituted or unsubstituted O or S Form a heterocycle,

R" and R"' are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group, or R" and R"' are the same as or different from each other, and each independently a substituted or unsubstituted aryl group, and R" And R"' is bonded to each other to form a substituted or unsubstituted aromatic ring,

R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Nitrile group; Halogen group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

R3 to R5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Nitrile group; Halogen group; Or an alkyl group,

m is an integer of 0 to 3, and when m is 2 or more, R1 is the same as or different from each other,

n is an integer of 0 to 4, and when n is 2 or more, R2 is the same as or different from each other.

In addition, the present application is a first electrode; A second electrode provided to face the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the aforementioned compound.

The compound according to the exemplary embodiment of the present application is used in an organic light-emitting device, thereby lowering a driving voltage of the organic light-emitting device, improving light efficiency, and improving lifespan characteristics of the device by thermal stability of the compound.

1 shows an example of an organic light emitting device in which a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4 are sequentially stacked.
2 shows an organic light-emitting device in which a substrate (1), an anode (2), a hole injection layer (5), a hole transport layer (6), a light-emitting layer (3), an electron transport layer (7), and a cathode (4) are sequentially stacked. It shows an example.
3 shows a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, an electron suppression layer 8, a light emitting layer 3, a hole blocking layer 9, an electron injection and transport layer ( 7-1) and a cathode 4 are shown in an example of an organic light-emitting device in which they are sequentially stacked.

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

The present specification provides a compound represented by Chemical Formula 1.

Examples of the substituent in the present specification are described below, but are not limited thereto.

The term "substituted" means that the hydrogen atom bonded to the carbon atom of the compound is replaced with another substituent, and the position to be substituted is not limited as long as the position where the hydrogen atom is substituted, that is, the position where the substituent can be substituted, and when two or more are substituted , Two or more substituents may be the same or different from each other.

In the present specification, the term "substituted or unsubstituted" refers to deuterium; Halogen group; Nitrile group; Nitro group; Alkyl group; Cycloalkyl group; Silyl group; Amine group; Aryl group; And it is substituted with one or two or more substituents selected from the group consisting of a heterocyclic group, two or more of the substituents exemplified above are substituted with a connected substituent, or does not have any substituents. For example, "a substituent to which two or more substituents are connected" may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent connected to two phenyl groups.

In the present specification, examples of the halogen group include fluorine, chlorine, bromine or iodine.

In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 50. Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl , Isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n -Heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethyl Heptyl, 1-ethylpropyl, 1,1-dimethylpropyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, and the like, but are not limited thereto.

In the present specification, the cycloalkyl group is not particularly limited, but is preferably 3 to 30 carbon atoms, and specifically, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, etc., but are limited thereto. It is not.

In the present specification, the silyl group is specifically trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, etc. However, it is not limited thereto.

In the present specification, the amine group is -NH ₂ ; Monoalkylamine group; Dialkylamine group; N-alkylarylamine group; Monoarylamine group; Diarylamine group; N-arylheteroarylamine group; It may be selected from the group consisting of an N-alkylheteroarylamine group, a monoheteroarylamine group, and a diheteroarylamine group, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of the amine group include methylamine group, dimethylamine group, ethylamine group, diethylamine group, phenylamine group, naphthylamine group, biphenylamine group, anthracenylamine group, 9-methyl-anthracenylamine group , Diphenylamine group, ditolylamine group, N-phenyltolylamine group, triphenylamine group, N-phenylbiphenylamine group, N-phenylnaphthylamine group, N-biphenylnaphthylamine group, N- Naphthylfluorenylamine group, N-phenylphenanthrenylamine group, N-biphenylphenanthrenylamine, N-phenylfluorenylamine group, N-phenylterphenylamine group, N-phenanthrenylfluore Nilamine group, N-biphenylfluorenylamine group, and the like, but are not limited thereto.

In the present specification, when the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but it is preferably 6 to 30 carbon atoms. Specifically, the monocyclic aryl group may be a phenyl group, a biphenyl group, or a terphenyl group, but is not limited thereto.

When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited. It is preferably 10 to 24 carbon atoms. Specifically, the polycyclic aryl group may be a naphthyl group, an anthracene group, a phenanthrene group, a pyrenyl group, a perylenyl group, a chrysene group, or a fluorene group, but is not limited thereto.

In the present specification, the heterocyclic group is an atom other than carbon and contains one or more heteroatoms, and specifically, the heteroatoms may include one or more atoms selected from the group consisting of O, N, Se, Si, and S, etc. have. The number of carbon atoms of the heterocyclic group is not particularly limited, but is preferably 2 to 60 carbon atoms or 2 to 30 carbon atoms. Examples of the heterocyclic group include thiophene group, furan group, pyrrole group, imidazolyl group, thiazolyl group, oxazolyl group, oxadiazolyl group, triazolyl group, pyridyl group, bipyridyl group, pyrimidyl group, tria Genyl group, acridyl group, pyridazinyl group, pyrazinyl group, quinolinyl group, quinazolinyl group, quinoxalinyl group, phthalazinyl group, pyridopyrimidinyl group, pyridopyrazinyl group, pyrazinopyrazinyl group , Isoquinolinyl group, indole group, carbazolyl group, benzoxazolyl group, benzimidazolyl group, benzothiazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, benzothiophene group, dibenzothiophene group , Benzofuran group, dibenzofuran group, benzosilol group, dibenzosilol group, phenanthrolinyl group, isoxazolyl group, thiadiazolyl group, phenothiazinyl group, phenoxazine group and their condensation structure, etc. However, it is not limited to these.

In the exemplary embodiment of the present specification, Ar1 to Ar4 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In the exemplary embodiment of the present specification, Ar1 to Ar4 are the same as or different from each other, and each independently a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted terphenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted anthracene group; A substituted or unsubstituted phenanthrene group; Or a substituted or unsubstituted triphenylene group.

In the exemplary embodiment of the present specification, Ar1 to Ar4 are the same as or different from each other, and each independently a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted terphenyl group; Or a substituted or unsubstituted naphthyl group.

In the exemplary embodiment of the present specification, Ar1 to Ar4 are the same as or different from each other, and each independently a phenyl group; Biphenyl group; Terphenyl group; Or a naphthyl group.

In the exemplary embodiment of the present specification, Ar1 and Ar3 are a phenyl group, and Ar2 and Ar4 are a phenyl group; Biphenyl group; Or a naphthyl group.

In the exemplary embodiment of the present specification, Ar1 to Ar4 are the same as each other.

In the exemplary embodiment of the present specification, Ar1 to Ar4 are phenyl groups.

In the exemplary embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently hydrogen; Halogen group; Nitrile group; Alkyl group; Or an aryl group.

In the exemplary embodiment of the present specification, R1 and R2 are hydrogen.

In the exemplary embodiment of the present specification, R3 to R5 are the same as or different from each other, and each independently hydrogen; Halogen group; Nitrile group; Or an alkyl group.

In the exemplary embodiment of the present specification, R3 to R5 are the same as or different from each other, and each independently hydrogen; F; Cl; Br; I; Nitrile group; Methyl group; Ethyl group; Propyl group; Or a butyl group.

In the exemplary embodiment of the present specification, R3 to R5 are the same as or different from each other, and each independently hydrogen; F; Nitrile group; Or a methyl group.

In the exemplary embodiment of the present specification, R3 to R5 are the same as or different from each other, and each independently hydrogen; Halogen group; Nitrile group; Or an alkyl group.

In an exemplary embodiment of the present specification, at least one of R3 to R5 is a halogen group; It is a nitrile group or an alkyl group, and the rest is hydrogen.

In an exemplary embodiment of the present specification, at least one of R3 to R5 is F; Nitrile group; Or a methyl group, and the rest are hydrogen.

In an exemplary embodiment of the present specification, one of R3 to R5 is F; Nitrile group; Or a methyl group, and the rest are hydrogen.

In the exemplary embodiment of the present specification, R3 is F; Nitrile group; Or a methyl group, and R4 and R5 are hydrogen.

In the exemplary embodiment of the present specification, R4 is F; A nitrile group or a methyl group, and R3 and R5 are hydrogen.

In an exemplary embodiment of the present specification, R3 is hydrogen; F; A nitrile group or a methyl group, and R4 and R5 are hydrogen.

In the exemplary embodiment of the present specification, R4 is hydrogen; F; Nitrile group; Or a methyl group, and R3 and R5 are hydrogen.

In an exemplary embodiment of the present specification, R3 to R5 are hydrogen.

In the exemplary embodiment of the present specification, X1 is S, O, or SO ₂ , and X2 is a direct bond.

In the exemplary embodiment of the present specification, X1 is S or O, and X2 is O, S, or CR"R"', and R" and R"' are the same as or different from each other, and each independently an alkyl group Or, R" and R"' are the same as or different from each other, each independently an aryl group, and are bonded to each other to form an aromatic ring.

In the exemplary embodiment of the present specification, X1 is S or O, and X2 is O, S, or CR"R"', and R" and R"' are the same as or different from each other, and each independently a methyl group , An ethyl group, a propyl group, or a butyl group, or R" and R"' are each a phenyl group, and are bonded to each other to form a fluorene ring.

In the exemplary embodiment of the present specification, X1 is S or O, X2 is O, S, or CR"R"', and R" and R"' are methyl groups, or R" and R"' are Each is a phenyl group, and is bonded to each other to form a fluorene ring.

In the exemplary embodiment of the present specification, X1 is CRR', X2 is a direct bond, the R and R'are the same as or different from each other, and each independently an aryl group or a heterocyclic group, and are bonded to each other to be substituted or It forms a heterocycle containing unsubstituted O or S.

In the exemplary embodiment of the present specification, X1 is CRR', X2 is a direct bond, R and R'are the same as or different from each other, and each independently an aryl group, and substituted or unsubstituted O by bonding to each other Or to form a heterocycle containing S.

In the exemplary embodiment of the present specification, X1 is CRR', X2 is a direct bond, the R and R'are the same as or different from each other, and each independently an aryl group, and are bonded to each other to include O or S. Form a heterocycle.

In the exemplary embodiment of the present specification, X1 is CRR', X2 is a direct bond, R and R'are each a phenyl group, and are bonded with O or S to form a thioxanthene ring or a xanthene ring.

In an exemplary embodiment of the present specification, the compound represented by Formula 1 is represented by one of the following Formulas 2 to 5.

[Formula 2]

[Formula 3]

[Formula 4]

[Formula 5]

In Formulas 2 to 5,

The definition of Ar1 to Ar4 is the same as the definition of Formula 1,

X3 is O; S; Or SO ₂ ,

X4 and X6 are the same as or different from each other, and each independently O; Or S,

X5 is O; S; Or CR"R"',

The R" and R"' are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group.

로 표시되는 구조는 하기 구조식들 중에서 선택된다.In an exemplary embodiment of the present specification, in Formula 1

The structure represented by is selected from the following structural formulas.

In an exemplary embodiment of the present specification, the compound represented by Formula 1 is selected from the following structural formulas.

The compound according to an exemplary embodiment of the present application may be prepared by a manufacturing method described below.

For example, the compound of Formula 1 may have a core structure as shown in the following General Formula 1. Substituents may be bonded by methods known in the art, and the type, position, or number of substituents may be changed according to techniques known in the art.

[General Formula 1]

In Reaction Scheme 1, Ar1, Ar2, X1, X2, R1, R2, m and n are as defined in Formula 1, and one implementation of the present specification by controlling Ar1, Ar2, X1, X2, R1 and R2 Compounds according to the state can be prepared.

In addition, the present specification provides an organic light-emitting device including the above-described compound.

In the exemplary embodiment of the present application, the first electrode; A second electrode provided to face the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the compound.

In the present specification, when a member is positioned "on" another member, this includes not only the case where a member is in contact with another member, but also the case where another member exists between the two members.

In the present specification, when a part "includes" a certain component, it means that other components may be further included rather than excluding other components unless specifically stated to the contrary.

The organic material layer of the organic light emitting device of the present application may have a single-layer structure, but may have a multilayer structure in which two or more organic material layers are stacked. For example, as a representative example of the organic light emitting device of the present invention, the organic light emitting device 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, and the like as an organic material layer. However, the structure of the organic light emitting device is not limited thereto and may include a smaller number of organic layers.

In the exemplary embodiment of the present application, the organic material layer includes an emission layer, and the emission layer includes the compound.

In the exemplary embodiment of the present application, the organic material layer includes a hole injection layer or a hole transport layer, and the hole injection layer or the hole transport layer includes the compound.

In the exemplary embodiment of the present application, the organic material layer includes a hole injection layer, a hole transport layer, or a hole injection and transport layer, and the hole injection layer, a hole transport layer, or the hole injection and transport layer includes the compound.

In the exemplary embodiment of the present application, the organic material layer includes an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer includes the compound.

In the exemplary embodiment of the present application, the organic material layer includes a hole blocking layer, and the hole blocking layer includes the compound.

In the exemplary embodiment of the present application, the organic material layer includes an electron injection layer, an electron transport layer, or an electron injection and transport layer, and the electron injection layer, the electron transport layer, or the electron injection and transport layer includes the compound.

In the exemplary embodiment of the present application, the organic light emitting device includes a first electrode; A second electrode provided to face the first electrode; And a light emitting layer provided between the first electrode and the second electrode. Two or more organic material layers are provided between the light-emitting layer and the first electrode, or between the light-emitting layer and the second electrode, and at least one of the two or more organic material layers includes the compound.

In the exemplary embodiment of the present application, the organic material layer further includes a hole injection layer or a hole transport layer including a compound including an arylamino group, carbazolyl group, or benzocarbazolyl group in addition to the organic material layer including the compound.

In another exemplary embodiment, the organic light-emitting device may be a normal type organic light-emitting device in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.

In another exemplary embodiment, the organic light-emitting device may be an inverted type organic light-emitting device in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate.

For example, the structure of an organic light-emitting device according to an exemplary embodiment of the present application is illustrated in FIGS. 1 and 2.

1 illustrates a structure of an organic light-emitting device in which a substrate 1, an anode 2, an emission layer 3, and a cathode 4 are sequentially stacked. In such a structure, the compound may be included in the emission layer 3.

2 shows an organic light-emitting device in which a substrate (1), an anode (2), a hole injection layer (5), a hole transport layer (6), a light-emitting layer (3), an electron transport layer (7), and a cathode (4) are sequentially stacked. The structure is illustrated. In such a structure, the compound may be included in one or more of the hole injection layer 5, the hole transport layer 6, the light emitting layer 3, and the electron transport layer 7.

3 shows a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, an electron suppression layer 8, a light emitting layer 3, a hole blocking layer 9, an electron injection and transport layer ( 7-1) and a cathode 4 are shown in an example of an organic light-emitting device in which they are sequentially stacked. In such a structure, the compound may be included in one or more of the hole injection layer 5, the hole transport layer 6, the emission layer 3, and the electron injection and transport layer 7-1.

In such a structure, the compound may be included in one or more of the hole injection layer, the hole transport layer, the light emitting layer, and the electron transport layer.

The organic light-emitting device of the present application may be manufactured by materials and methods known in the art, except that at least one of the organic material layers includes the compound of the present application, that is, the compound.

When the organic light-emitting device includes a plurality of organic material layers, the organic material layers may be formed of the same material or different materials.

For example, the organic light emitting device of the present application may be manufactured by sequentially laminating a first electrode, an organic material layer, and a second electrode on a substrate. At this time, by using a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation, a metal or conductive metal oxide or alloy thereof is deposited on the substrate to form an anode. And, after forming an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer thereon, it can be prepared by depositing a material that can be used as a cathode thereon. In addition to this method, an organic light-emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.

In addition, the compound of Formula 1 may be formed as an organic material layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light emitting device. Here, the solution coating method refers to spin coating, dip coating, doctor blading, ink jet printing, screen printing, spray method, roll coating, and the like, but is not limited thereto.

In addition to such a method, an organic light-emitting device may be manufactured by sequentially depositing an organic material layer and an anode material from a cathode material on a substrate (International Patent Application Publication No. 2003/012890). However, the manufacturing method is not limited thereto.

In the exemplary embodiment of the present application, the first electrode is an anode, and the second electrode is a cathode.

In another exemplary embodiment, the first electrode is a cathode, and the second electrode is an anode.

As the anode material, a material having a large work function is preferable so that holes can be smoothly injected into the organic material layer. Specific examples of the anode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); A combination of metal and oxide such as ZnO:Al or SnO _{2 :Sb;} Poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), conductive polymers such as polypyrrole and polyaniline, and the like, but are not limited thereto.

It is preferable that the cathode material is a material having a small work function to facilitate electron injection into the organic material 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; There are multilayered materials such as LiF/Al or LiO ₂ /Al, but are not limited thereto.

The hole injection layer is a layer that injects holes from an electrode, and has the ability to transport holes as a hole injection material, so that it has a hole injection effect at the anode, an excellent hole injection effect for a light emitting layer or a light emitting material, and is generated from the light emitting layer. A compound that prevents the movement of excitons to the electron injection layer or the electron injection material and has excellent ability to form a thin film is preferable. It is preferable that the HOMO (highest occupied molecular orbital) of the hole injection material is between the work function of the positive electrode material and the HOMO of the surrounding organic material layer. Specific examples of hole injection materials include metal porphyrin, oligothiophene, arylamine-based organic substances, hexanitrile hexaazatriphenylene-based organic substances, quinacridone-based organic substances, and perylene-based organic substances. Organic substances, anthraquinone, polyaniline, and polythiophene-based conductive polymers, but are not limited thereto.

The hole transport layer is a layer that receives holes from the hole injection layer and transports holes to the emission layer.The hole transport material is a material capable of transporting holes from the anode or the hole injection layer to the emission layer, and has high mobility for holes. The material is suitable. Specific examples include an arylamine-based organic material, a conductive polymer, and a block copolymer including a conjugated portion and a non-conjugated portion, but are not limited thereto.

As the light-emitting material, a material capable of emitting light in a visible light region by transporting 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 compound; Benzoxazole, benzthiazole, and benzimidazole-based compounds; Poly(p-phenylenevinylene) (PPV)-based polymer; Spiro compounds; Polyfluorene, rubrene, and the like, but are not limited thereto.

The emission layer may include a host material and a dopant material. Host materials include condensed aromatic ring derivatives or heterocyclic-containing compounds. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds, and heterocycle-containing compounds include compounds, dibenzofuran derivatives, and ladder furan compounds. , Pyrimidine derivatives, and the like, but are not limited thereto.

The electron transport layer is a layer that receives electrons from the electron injection layer and transports electrons to the emission layer. As an electron transport material, a material capable of receiving electrons from the cathode and transferring them to the emission layer. This is suitable. Specific examples include Al complex of 8-hydroxyquinoline; Complexes containing Alq _3; Organic radical compounds; Hydroxyflavone-metal complexes and the like, but are not limited thereto. The electron transport layer can be used with any desired cathode material as used according to the prior art. In particular, examples of suitable cathode materials are conventional materials that have a low work function and are followed by an aluminum layer or a silver layer. Specifically, they are cesium, barium, calcium, ytterbium, and samarium, and in each case an aluminum layer or a silver layer follows.

The electron injection layer is a layer that injects electrons from the electrode, has the ability to transport electrons, has an electron injection effect from the cathode, an excellent electron injection effect on the light emitting layer or light emitting material, and injects holes of excitons generated from the light emitting layer. A compound that prevents migration to the layer and is excellent in thin film forming ability is preferable. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, preorenylidene methane, anthrone, etc. Complex compounds and nitrogen-containing 5-membered ring derivatives, but are not limited thereto.

Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese, Tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h] Quinolinato)beryllium, bis(10-hydroxybenzo[h]quinolinato)zinc, bis(2-methyl-8-quinolinato)chlorogallium, bis(2-methyl-8-quinolinato)( o-cresolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtholato)aluminum, bis(2-methyl-8-quinolinato)(2-naphtholato)gallium, etc. It is not limited to this.

The hole blocking layer is a layer that prevents holes from reaching the cathode, and may be generally formed under the same conditions as the hole injection layer. Specifically, there are oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, aluminum complexes, etc., but are not limited thereto.

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

The preparation of the compound represented by Formula 1 and the organic light-emitting device including the same will be described in detail in the following examples. However, the following examples are for illustrative purposes only, and the scope of the present specification is not limited thereto.

< Manufacturing example >

[Scheme 1]

[Scheme 2]

[Scheme 3]

[Scheme 4]

[Scheme 5]

Manufacturing example 1. Preparation of compound 1

Compound 2-chloro-4,6-diphenyl-1,3,5-triazine (6.50 g, 14.98 mmol), and compound 1-1 (5.82 g, 16.47 mmol) were added to a 500 mL round bottom flask in a nitrogen atmosphere. After completely dissolving in 240 mL of tetrahydrofuran, 2M aqueous potassium carbonate solution (120 mL) was added, tetrakis-(triphenylphosphine) palladium (0.52 g, 0.45 mmol) was added, followed by heating and stirring for 3 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 250 mL of ethyl acetate to prepare compound 1 (7.11 g, 71%).

MS[M+H] ⁺ = 707

Manufacturing example 2. Preparation of compound 2

Compound 2 was prepared in the same manner as in Preparation Example 1, except that Compound 1-2 was used instead of Compound 1-1 in Preparation Example 1.

MS[M+H] ⁺ = 707

Preparation Example 3. Preparation of compound 3

Compound 3 was prepared in the same manner as in Preparation Example 1, except that Compound 1-3 was used instead of Compound 1-1 in Preparation Example 1.

MS[M+H] ⁺ = 707

Preparation Example 4. Preparation of compound 4

Compound 4 was prepared in the same manner as in Preparation Example 1, except that Compound 1-4 was used instead of Compound 1-1 in Preparation Example 1.

MS[M+H] ⁺ = 707

Preparation Example 5. Preparation of compound 5

Compound 2-chloro-4,6-phenyl-1,3,5-triazine (6.50 g, 14.98 mmol), and compound 2-1 (5.82 g, 16.47 mmol) in a 500 mL round-bottom flask in a nitrogen atmosphere were tetra-treated with tetrahydrofuran. After completely dissolving in 240 mL of hydrofuran, 2M aqueous potassium carbonate solution (120 mL) was added, tetrakis-(triphenylphosphine) palladium (0.52 g, 0.45 mmol) was added, followed by heating and stirring for 3 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 250 mL of ethyl acetate to prepare compound 5 (7.11 g, 71%).

MS[M+H] ⁺ = 723

Preparation Example 6. Preparation of compound 6

Compound 6 was prepared in the same manner as in Preparation Example 5, except that Compound 2-2 was used instead of Compound 2-1 in Preparation Example 5.

MS[M+H] ⁺ = 723

Preparation Example 7. Preparation of compound 7

Compound 7 was prepared in the same manner as in Preparation Example 5, except that Compound 2-3 was used instead of Compound 2-1 in Preparation Example 5.

MS[M+H] ⁺ = 723

Preparation Example 8. Preparation of compound 8

Compound 8 was prepared in the same manner as in Preparation Example 5, except that Compound 2-4 was used instead of Compound 2-1 in Preparation Example 5.

MS[M+H] ⁺ = 723

Preparation Example 9. Preparation of compound 9

Compound 2-chloro-4,6-diphenyl-1,3,5-triazine (6.50 g, 14.98 mmol), and compound 3-1 (5.82 g, 16.47 mmol) were added to a 500 mL round bottom flask in a nitrogen atmosphere. After completely dissolving in 240 mL of tetrahydrofuran, 2M aqueous potassium carbonate solution (120 mL) was added, tetrakis-(triphenylphosphine) palladium (0.52 g, 0.45 mmol) was added, followed by heating and stirring for 3 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 250 mL of ethyl acetate to prepare compound 9 (7.11 g, 71%).

MS[M+H] ⁺ = 739

Preparation Example 10 Preparation of Compound 10

Compound 10 was prepared in the same manner as in Preparation Example 9, except that Compound 3-2 was used instead of Compound 3-1 in Preparation Example 9.

MS[M+H] ⁺ = 755

Preparation Example 11. Preparation of compound 11

Compound 11 was prepared in the same manner as in Preparation Example 9, except that Compound 3-3 was used instead of Compound 3-1 in Preparation Example 9.

MS[M+H] ⁺ = 723

Preparation Example 12. Synthesis of Compound 12

Compound 12 was prepared in the same manner as in Preparation Example 9, except that Compound 3-4 was used instead of Compound 3-1 in Preparation Example 9.

MS[M+H] ⁺ = 723

Preparation Example 13. Preparation of compound 13

Compound 2-chloro-4,6-diphenyl-1,3,5-triazine (5.50 g, 12.67 mmol), and compound 4-1 (6.15 g, 13.94 mmol) were added to a 500 mL round bottom flask in a nitrogen atmosphere. After completely dissolving in 240 mL of tetrahydrofuran, 2M aqueous potassium carbonate solution (120 mL) was added, tetrakis-(triphenylphosphine) palladium (0.44 g, 0.38 mmol) was added, followed by heating and stirring for 3 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 240 mL of ethyl acetate to prepare compound 13 (8.13 g, 85%).

MS[M+H] ⁺ = 887

Preparation Example 14 Preparation of Compound 14

Compound 14 was prepared in the same manner as in Preparation Example 13, except that Compound 4-2 was used instead of Compound 4-1 in Preparation Example 13.

MS[M+H] ⁺ = 723

Preparation Example 15. Preparation of compound 15

Compound 15 was prepared in the same manner as in Preparation Example 13, except that Compound 4-3 was used instead of Compound 4-1 in Preparation Example 13.

MS[M+H] ⁺ = 871

Preparation Example 16. Synthesis of Compound 16

Compound 16 was prepared in the same manner as in Preparation Example 13, except that Compound 4-4 was used instead of Compound 4-1 in Preparation Example 13.

MS[M+H] ⁺ = 871

Preparation Example 17. Synthesis of Compound 17

Compound 2-chloro-4,6-diphenyl-1,3,5-triazine (4.50 g, 16.85 mmol), and compound 5-1 (4.39 g, 8.43 mmol) were added to a 500 mL round bottom flask in a nitrogen atmosphere. After completely dissolving in 280 mL of tetrahydrofuran, 2M aqueous potassium carbonate solution (140 mL) was added, tetrakis-(triphenylphosphine) palladium (0.55 g, 0.0.51 mmol) was added, followed by heating and stirring for 3 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 210 mL of ethyl acetate to prepare compound 17 (7.76 g, 63%).

MS[M+H] ⁺ = 732

Preparation Example 18. Synthesis of Compound 18

Compound 18 was prepared in the same manner as in Preparation Example 17, except that Compound 5-2 was used instead of Compound 5-1 in Preparation Example 17.

MS[M+H] ⁺ = 737

Preparation Example 19. Synthesis of Compound 19

Compound 19 was prepared in the same manner as in Preparation Example 17, except that Compound 5-3 was used instead of Compound 5-1 in Preparation Example 17.

MS[M+H] ⁺ = 757

Preparation Example 20. Synthesis of Compound 20

Compound 20 was prepared in the same manner as in Preparation Example 17, except that Compound 5-4 was used instead of Compound 5-1 in Preparation Example 17.

MS[M+H] ⁺ = 769

Example 1-1

A glass substrate coated with a thin film of ITO (indium tin oxide) having a thickness of 1,000Å was put in distilled water dissolved in a detergent and washed with ultrasonic waves. At this time, a product made by Fischer Co. was used as a detergent, and distilled water secondarily filtered with a filter manufactured by Millipore Co. was used as distilled water. After washing the ITO for 30 minutes, it was repeated twice with distilled water to perform ultrasonic cleaning for 10 minutes. After washing with distilled water, ultrasonic washing was performed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner. In addition, after cleaning the substrate for 5 minutes using oxygen plasma, the substrate was transported to a vacuum evaporator.

A hole injection layer was formed by thermally vacuum depositing a compound of the following compound HI1 and the following compound HI2 to a thickness of 100 Å in a ratio of 98:2 (molar ratio) on an ITO transparent electrode, which is an anode thus prepared. A hole transport layer was formed by vacuum depositing a compound (1150Å) represented by the following formula HT1 on the hole injection layer. Subsequently, an electron suppressing layer was formed by vacuum depositing a compound of EB1 with a film thickness of 50 Å on the hole transport layer. Subsequently, a light emitting layer was formed by vacuum depositing a compound represented by the following formula BH and a compound represented by the following formula BD with a film thickness of 200 Å on the electron suppressing layer at a weight ratio of 25:1. A hole blocking layer was formed by vacuum depositing the following HB 1 with a film thickness of 50 Å on the emission layer. Subsequently, on the hole blocking layer, the compound 1 synthesized in Preparation Example 1 and the compound represented by LiQ were vacuum-deposited at a weight ratio of 1:1 to form an electron injection and transport layer with a thickness of 310Å. Lithium fluoride (LiF) in a thickness of 12 Å and aluminum in a thickness of 1,000 Å were sequentially deposited on the electron injection and transport layer to form a negative electrode.

In the above process, the deposition rate of the organic material was maintained at 0.4 ~ 0.7Å/sec, the deposition rate of lithium fluoride at the negative electrode was 0.3Å/sec, and the deposition rate of aluminum was 2Å/sec, and the vacuum degree during deposition was 2×10 ^{− Maintaining 7} ~ 5 × 10 ^-6 torr, an organic light emitting device was manufactured.

Examples 1-2 to 1-20

An organic light-emitting device was manufactured in the same manner as in Example 1-1, except that the compound shown in Table 1 was used instead of Compound 1 of Preparation Example 1.

Comparative Examples 1-1 to 1-6

An organic light-emitting device was manufactured in the same manner as in Example 1-1, except that the compound shown in Table 1 was used instead of Compound 1 of Preparation Example 1.

The compounds of ET1 to ET6 used in Table 1 are as follows.

Experimental Example 1

When a current was applied to the organic light emitting device prepared in the above Examples and Comparative Examples, voltage, efficiency, color coordinates, and lifetime were measured, and the results are shown in Table 1 below. T95 refers to the time it takes for the luminance to decrease from the initial luminance (1600 nit) to 95%.

compound
(Electron injection and transport layer) Voltage
(V@20mA
/cm ² ) efficiency
(cd/A@20mA
/cm ² ) Color coordinates
(x,y) T95
(hr) Example 1-1 Compound 1 3.41 6.41 (0.142, 0.045) 285 Example 1-2 Compound 2 3.43 6.46 (0.141, 0.046) 280 Example 1-3 Compound 3 3.46 6.48 (0.143, 0.047) 290 Example 1-4 Compound 4 3.42 6.48 (0.139, 0.046) 280 Example 1-5 Compound 5 3.30 6.59 (0.141, 0.045) 275 Example 1-6 Compound 6 3.33 6.54 (0.141, 0.047) 275 Example 1-7 Compound 7 3.34 6.55 (0.142, 0.046) 270 Example 1-8 Compound 8 3.38 6.53 (0.139, 0.045) 275 Example 1-9 Compound 9 3.53 6.42 (0.143, 0.046) 265 Example 1-10 Compound 10 3.51 6.49 (0.142, 0.046) 255 Example 1-11 Compound 11 3.56 6.47 (0.140, 0.047) 255 Example 1-12 Compound 12 3.55 6.46 (0.141, 0.045) 250 Example 1-13 Compound 13 3.63 6.35 (0.141, 0.046) 265 Example 1-14 Compound 14 3.63 6.37 (0.142, 0.047) 260 Example 1-15 Compound 15 3.73 6.28 (0.140, 0.046) 265 Example 1-16 Compound 16 3.73 6.21 (0.141, 0.045) 260 Example 1-17 Compound 17 3.53 6.44 (0.142, 0.046) 255 Example 1-18 Compound 18 3.56 6.49 (0.142, 0.045) 250 Example 1-19 Compound 19 3.58 6.43 (0.141, 0.046) 265 Example 1-20 Compound 20 3.59 6.41 (0.142, 0.046) 270 Comparative Example 1-1 ET1 4.37 5.42 (0.139, 0.041) 130 Comparative Example 1-2 ET2 3.82 6.03 (0.141, 0.042) 210 Comparative Example 1-3 ET3 3.84 6.01 (0.139, 0.041) 225 Comparative Example 1-4 ET4 4.25 5.56 (0.141, 0.042) 180 Comparative Example 1-5 ET5 4.52 5.25 (0.142, 0.043) 165 Comparative Example 1-6 ET6 3.93 5.87 (0.143, 0.044) 125

As shown in Table 1, the organic light-emitting device using the compound of the present invention as an electron injection and transport layer exhibited excellent characteristics in terms of efficiency, driving voltage, and stability of the organic light-emitting device.

In Comparative Examples 1-1 and 1-4, an organic light-emitting device manufactured by using a compound in which a heteroaryl group (carbazole-based material) containing N is substituted on the core phenyl side of the present invention as an electron injection and transport layer Showed poor characteristics due to the collapse of the charge balance.

In Comparative Examples 1-5 and 1-6, the organic light emitting device manufactured by using the compound in which R3 to R5 of the core phenyl side of the present invention is an aryl group or carbazole as an electron injection and transport layer also has poor characteristics.

In Comparative Examples 1-2 and 1-3, the material in which the aryl group was substituted on the benzene core side of the present invention was similar in voltage and efficiency characteristics to the compound of the present invention, but was inferior in lifespan characteristics. The compounds of the present invention are considered to have increased stability and significantly improved lifespan characteristics, including a heteroaryl group containing an S or O atom, which is relatively more resistant to electrons than a heteroaryl group containing an aryl group and an N.

As shown in the results of Table 1, it was confirmed that the compound according to the present invention has excellent electron transport and injection ability, and thus can be applied to an organic light emitting device.

Preferred embodiments of the present invention (electron transport and injection layer) have been described above, but the present invention is not limited thereto, and various modifications can be made within the scope of the claims and the detailed description of the invention. This also falls within the scope of the invention.

1: substrate
2: anode
3: light-emitting layer
4: cathode
5: hole injection layer
6: hole transport layer
7: electron transport layer
7-1: electron injection and transport layer
8: electron suppression layer
9: hole block

Claims (9)

Compound represented by the following formula (1):
[Formula 1]

In Formula 1,
Ar1 to Ar4 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group,
X1 is S; O; SO ₂ ; Or CRR',
X2 is a direct bond; O; S; Or CR"R"',
R and R'are bonded to each other to form a heterocycle including a substituted or unsubstituted O or S,
R" and R"' are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group, or R" and R"' are the same as or different from each other, and each independently a substituted or unsubstituted aryl group, and R" And R"' is bonded to each other to form a substituted or unsubstituted aromatic ring,
R1 and R2 are the same as or different from each other, and each independently hydrogen; Or deuterium,
R3 to R5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Nitrile group; Halogen group; Or an alkyl group,
m is an integer of 0 to 3, and when m is 2 or more, R1 is the same as or different from each other,
n is an integer of 0 to 4, and when n is 2 or more, R2 is the same as or different from each other. The method according to claim 1, wherein Ar1 to Ar4 are the same as or different from each other, and each independently a phenyl group; Biphenyl group; Terphenyl group; Or a compound that is a naphthyl group. The compound of claim 1, wherein Ar1 to Ar4 are the same as each other. The compound of claim 1, wherein the compound represented by Formula 1 is represented by one of the following Formulas 2 to 5:
[Formula 2]

[Formula 3]

[Formula 4]

[Formula 5]

In Formulas 2 to 5,
The definition of Ar1 to Ar4 is the same as the definition of Formula 1,
X3 is O; S; Or SO ₂ ,
X4 and X6 are the same as or different from each other, and each independently O; Or S,
X5 is O; S; Or CR"R"',
The R" and R"' are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group. The compound of claim 1, wherein the compound represented by Formula 1 is selected from the following structural formulas:

A first electrode; A second electrode provided to face the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers comprises the compound according to any one of claims 1 to 5 device. The method of claim 6,
The organic material layer includes a hole blocking layer, and the hole blocking layer is an organic light-emitting device including the compound. The organic light-emitting device of claim 6, wherein the organic material layer includes an emission layer, and the emission layer includes the compound. The organic light-emitting device of claim 6, wherein the organic material layer includes an electron injection layer, an electron transport layer, or an electron injection and transport layer, and the electron injection layer, the electron transport layer, or the electron injection and transport layer includes the compound.

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