KR20200042428A - Novel compound and organic light emitting device comprising the same - Google Patents

Abstract

The present invention provides a novel compound and an organic light emitting device using the same, wherein the compound is represented by chemical formula 1. The compound can improve lifespan characteristics in the organic light emitting device.

Description

A novel compound and an organic light-emitting device comprising the same {NOVEL COMPOUND AND ORGANIC LIGHT EMITTING DEVICE COMPRISING THE SAME}

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

In general, the organic light emitting phenomenon refers to a phenomenon that converts electrical energy into light energy using an organic material. The organic light emitting device using the organic light emitting phenomenon has a wide viewing angle, excellent contrast, and fast response time, and has excellent luminance, driving voltage, and response speed characteristics, and thus many studies have been conducted.

The organic light emitting device generally has a structure including an anode and a cathode and an organic material layer between the anode and the cathode. In order to increase the efficiency and stability of the organic light emitting device, the organic material layer is often formed of a multi-layered structure composed of different materials, for example, may be formed of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like. When a voltage is applied between the two electrodes in the structure of the organic light emitting device, holes are injected at the anode, and electrons are injected at the cathode, and an exciton is formed when the injected holes meet the electrons. When it falls to the ground again, it will shine.

The development of new materials for organic materials used in the organic light emitting device as described above is continuously required.

Korean Patent Publication No. 10-2000-0051826

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

The present invention provides a compound represented by Formula 1:

[Formula 1]

In Chemical Formula 1,

Ar ₁ and Ar ₂ are each independently C _6-60 aryl; Or a substituted or unsubstituted C _5-60 heteroaryl containing any one or more heteroatoms selected from the group consisting of N, O and S,

Ar ₃ and Ar ₄ are each independently C _6-60 aryl, provided that at least one of Ar ₃ and Ar ₄ is biphenylyl or naphthyl.

In addition, the present invention is a first electrode; A second electrode provided to face the first electrode; And an organic light emitting device including at least one layer of an organic material provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer includes a compound represented by Chemical Formula 1, and provides an organic light emitting device. do.

The compound according to the present invention may be used as a material for an organic material layer of an organic light emitting device, and may improve efficiency, low driving voltage, and / or life characteristics in an organic light emitting device.

FIG. 1 shows an example of an organic light emitting device including a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4.
FIG. 2 shows an example of an organic light emitting device comprising a substrate 1, an anode 2, a hole transport layer 5, an electron suppressing layer 6, a light emitting layer 3, an electron transport layer 7, and a cathode 4 It is done.
3 shows a substrate 1, an anode 2, a hole injection layer 8, a hole transport layer 5, an electron suppression layer 6, a light emitting layer 3, a hole suppression layer 9, and an electron transport layer 7 And an example of an organic light-emitting device comprising the cathode 4.

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

는 다른 치환기에 연결되는 결합을 의미한다. In this specification,

Means a linkage to another substituent.

The term "substituted or unsubstituted" as used herein refers to deuterium; Halogen group; Nitrile group; Nitro group; Hydroxy group; Carbonyl group; Ester groups; Imide group; Amino group; Phosphine oxide group; Alkoxy groups; Aryloxy group; Alkyl thioxy group; Arylthioxy group; Alkyl sulfoxy group; Aryl sulfoxyl group; Silyl group; Boron group; Alkyl groups; Cycloalkyl group; Alkenyl group; Aryl group; Aralkyl group; An alkenyl group; Alkyl aryl groups; Alkylamine groups; Aralkylamine group; Heteroarylamine group; Arylamine group; Arylphosphine group; Or substituted or unsubstituted with one or more substituents selected from the group consisting of heterocyclic groups containing one or more of N, O and S atoms, or substituted or unsubstituted with two or more substituents among the exemplified substituents above . For example, "a substituent having two or more substituents" may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent to which two phenyl groups are connected.

In the present specification, the number of carbon atoms of the carbonyl group is not particularly limited, but is preferably 1 to 40 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.

In the present specification, the oxygen of the ester group may be substituted with a straight chain, branched or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 25 carbon atoms. Specifically, it may be a compound of the following structural formula, but is not limited thereto.

In this specification, the number of carbon atoms of the imide group is not particularly limited, but is preferably 1 to 25 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.

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 boron group is specifically a trimethyl boron group, a triethyl boron group, a t-butyldimethyl boron group, a triphenyl boron group, a phenyl boron group, and the like, but is not limited thereto.

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

In the present specification, the alkyl group may be straight chain or branched chain, and carbon number is not particularly limited, but is preferably 1 to 40. According to an exemplary embodiment, the alkyl group has 1 to 20 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 10 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 6 carbon atoms. Specific examples of the alkyl group are 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 -Dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, and the like, but is not limited thereto.

In the present specification, the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the carbon number of the alkenyl group is 2 to 20. According to another exemplary embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 6 carbon atoms. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1- Butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2- ( Naphthyl-1-yl) vinyl-1-yl, 2,2-bis (diphenyl-1-yl) vinyl-1-yl, steelbenyl group, styrenyl group, and the like, but are not limited thereto.

In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and according to an exemplary embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 6 carbon atoms. 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, and the like, but is not limited thereto.

In the present specification, the aryl group is not particularly limited, but is preferably 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the carbon number of the aryl group is 6 to 30. According to one embodiment, the carbon number of the aryl group is 6 to 20. The aryl group may be a phenyl group, a biphenylyl group, a terphenyl group, a quarterphenyl group, etc., as a monocyclic aryl group, but is not limited thereto. The polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthrenyl group, triphenylenyl group, pyrenyl group, perylenyl group, chrysenyl group, fluorenyl group, and the like, but is not limited thereto.

등이 될 수 있다. 다만, 이에 한정되는 것은 아니다.In the present specification, the fluorenyl group may be substituted, and two substituents may combine with each other to form a spiro structure. When the fluorenyl group is substituted,

It can be back. However, it is not limited thereto.

In the present specification, the heterocyclic group is a heterocyclic group containing one or more of O, N, Si, and S as heterogeneous elements, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60 carbon atoms. Examples of the heterocyclic group include thiophene group, furan group, pyrrol group, imidazole group, thiazole group, oxazole group, oxadiazole group, triazole group, pyridyl group, bipyridyl group, pyrimidyl group, triazine group, acridil group , Pyridazine group, pyrazinyl group, quinolinyl group, quinazolinyl group, quinoxalinyl group, phthalazinyl group, pyridopyrimidinyl group, pyrido pyrazinyl group, pyrazino pyrazinyl group, isoquinoline group, indole group , Carbazole group, benzoxazole group, benzoimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group, phenanthroline, isooxazolyl group, tiadia A sleepy group, a phenothiazinyl group and a dibenzofuranyl group, and the like, but are not limited thereto.

In the present specification, an aryl group in an aralkyl group, an alkenyl group, an alkylaryl group, and an arylamine group is the same as the exemplified aryl group described above. In the present specification, the alkyl group among the aralkyl group, alkylaryl group, and alkylamine group is the same as the above-described alkyl group. In the present specification, the description of the heteroaryl group among heteroarylamines may be applied. In the present specification, the alkenyl group in the alkenyl group is the same as the exemplified alkenyl group. In the present specification, the description of the aryl group described above may be applied, except that the arylene is a divalent group. In the present specification, the description of the heterocyclic group described above may be applied, except that the heteroarylene is a divalent group. In the present specification, the hydrocarbon ring is not a monovalent group, and a description of the aryl group or cycloalkyl group described above may be applied, except that two substituents are formed by bonding. In the present specification, the heterocycle is not a monovalent group, and the description of the aforementioned heterocyclic group may be applied, except that two substituents are formed by bonding.

The present invention provides a compound represented by Formula 1 above.

The compound represented by Chemical Formula 1 is a phenyl group that is attached to an amine nitrogen atom of a triarylamine, and introduces an aryl group only at an ortho position with respect to a nitrogen atom. By controlling the LUMO energy level, an excellent effect of controlling the energy barrier with each organic layer can be obtained.

Specifically, Ar ₁ silver and Ar ₂ are each independently C _6-30 aryl, or C _6-28 aryl, or C _6-25 aryl, or any one or more selected from the group consisting of N, O and S It may be a substituted or unsubstituted C _5-30 heteroaryl containing heteroatoms, or C _8-20 heteroaryl, or C _12-18 heteroaryl. Preferably, Ar ₁ and Ar ₂ are each independently phenyl, biphenylyl, terphenylyl, quarterphenylyl, naphthyl, phenanthrenyl, triphenylenyl, dimethylfluorenyl, diphenylfluorenyl, Dibenzofuranyl, dibenzothiophenyl, 9-phenyl-9H-carbazolyl, phenyl substituted with naphthyl, phenyl substituted with phenanthrenyl, or phenyl substituted with triphenylenyl.

Specifically, Ar ₃ and Ar ₄ may each independently be C _6-30 aryl, or C _6-25 aryl, or C _6-18 aryl. Preferably, Ar ₃ and Ar ₄ are each independently phenyl, biphenylyl, terphenylyl, or naphthyl.

Specifically, Ar ₁ and Ar ₂ , and Ar ₃ and Ar ₄ may be the same or different from each other.

For example, at least one pair of Ar ₁ and Ar ₂ , and Ar ₃ and Ar ₄ may be the same as each other. For example, Ar ₁ and Ar ₂ are the same as each other, and Ar ₃ and Ar ₄ may be different from each other. Alternatively, Ar ₁ and Ar ₂ are different from each other, and Ar ₃ and Ar ₄ may be identical to each other. Alternatively, Ar ₁ and Ar ₂ may be identical to each other, and Ar ₃ and Ar ₄ may be identical to each other.

Here, when Ar ₁ and Ar ₂ are the same as each other, Ar ₂ and Ar ₂ may be phenyl, biphenylyl, terphenylyl, naphthyl, or dimethylfluorenyl.

For example, the compound represented by Formula 1 may be represented by any one of the following Formulas 1-1 to 1-12.

[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

[Formula 1-5]

[Formula 1-6]

[Formula 1-7]

[Formula 1-8]

[Formula 1-9]

[Formula 1-10]

[Formula 1-11]

[Formula 1-12]

In Chemical Formulas 1-1 to 1-12,

Ar ₁ and Ar _-2 are as defined in Chemical Formula 1,

R ₁ , R ₂ , R ₃ , R ₄ , and R ₅ are each independently hydrogen, deuterium, halogen group, nitrile group, silyl group, C _6-60 aryl, C _6-60 aralkyl, C _6-60 Aralkenyl; Or a substituted or unsubstituted C _5-60 heteroaryl containing any one or more heteroatoms selected from the group consisting of N, O and S.

Specifically, R ₁ , R ₂ , R ₃ , R ₄ , and R ₅ may be hydrogen.

On the other hand, the compound represented by the formula (1), Ar ₁ , Ar ₂ substituted on the amine nitrogen atom of the triarylamine may be to include all of the structural isomers (stereo-isomer) having a different left and right positions through rotation. .

Representative examples of the compound represented by Formula 1 are as follows.

Meanwhile, the compound represented by Chemical Formula 1 may be prepared in the same manner as in Reaction Schemes 1 to 2 below.

[Scheme 1]

[Scheme 2]

In Reaction Schemes 1 to 2, Ar ₁ , Ar _-2 , Ar ₃ , and Ar- ₄ are as defined in Chemical Formula 1, and X ₁ to X ₄ are each independently a halogen group.

Specifically, Reaction Scheme 1 is a reaction in which aryl groups (Ar ₃ and Ar ₄ ) are introduced at both sides of an ortho position of phenyl amine.

Reaction Scheme 1 may be performed using a palladium catalyst (Pd catalyst) in the presence of a base. For example, in the reaction scheme 1, potassium carbonate (K ₂ CO ₃ ) may be used as the base component, and bis (tri-tert-butylphosphine) palladium (BTP, bis (tri-tert-butylphosphine) may be used as a palladium catalyst. ) palladium).

Reaction (I) in Reaction Scheme 1 is a reaction in which an aryl group is introduced at one of the ortho positions of phenyl amine, and a phenyl amine substituted with a halogen group at the ortho position is a palladium catalyst in the presence of a base. It consists of reacting with aryl boronic acid (Ar ₃ -B (OH) ₂ ) using (Pd catalyst). Thus, after introducing an aryl group to one of the ortho (ortho) positions of the phenyl amine, and reacted with a separate aryl boronic acid (Ar ₄ -B (OH) ₂ ) as in the reaction (II) in the above scheme 1 of All of the ortho (ortho) position is to introduce an aryl group.

Here, when Ar ₃ and Ar ₄ are the same, the reaction (II) in the scheme 1 is omitted, and the reaction (I) is a one-step reaction in which aryl groups are introduced at both of the ortho positions of the phenyl amine at once. Can be done.

In addition, Reaction Scheme 2 is a reaction in which an aryl or heteroaryl group (Ar ₁ , Ar ₂ ) is additionally introduced into a phenyl amine in which a halogen group is substituted at an ortho position generated through Scheme 1.

In addition, Reaction Scheme 2 may be performed using a palladium catalyst (Pd catalyst) in the presence of a base. In the reaction scheme 2, sodium tert-butoxide (NaOtBu) or the like may be used as the base component, and bis (tri-tert-butylphosphine) palladium (BTP) or 1,1'-bis (diphenyl) may be used as the Pd catalyst. Phosphino) ferrocene dichloro palladium (II) (Pd (dppf) Cl ₂ ) and the like can be used.

Reaction (III) in Reaction Scheme 2 is a palladium catalyst (Pd catalyst) in the presence of a base in which a halogen group is substituted at the ortho position generated through Reaction Scheme 1, that is, diaryl phenyl amine is present in the base. It consists of reacting with a halide (Ar ₁ -X ₃ ) containing aryl or heteroaryl to be substituted. After introducing the aryl or heteroaryl instead of hydrogen in the diaryl phenyl amine through the reaction (III), a halide containing a separate aryl or heteroaryl (Ar ₂ -X) as in the reaction (IV) in Reaction Scheme 1 above _It reacts with ₄ ) to introduce all aryl or heteroaryl instead of the rest of the hydrogen in the phenyl amine. Preferably, X ₃ and X ₄ are each independently bromo or chlorol.

Here, when Ar ₁ and Ar ₂ are the same, the reaction (IV) is omitted in Reaction Scheme 2, and in the reaction (III), aryl or heteroaryl is introduced into both at once instead of two hydrogens of diaryl phenyl amine. It can be carried out in a step reaction.

In the manufacturing method according to the above reaction schemes 1 to 2, the reactor for the amine substitution reaction can be changed as known in the art. The manufacturing method may be more specific in the manufacturing examples to be described later.

In addition, the present invention provides an organic light emitting device comprising the compound represented by the formula (1). In one example, the present invention is a first electrode; A second electrode provided to face the first electrode; And an organic light emitting device including at least one layer of an organic material provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer includes a compound represented by Chemical Formula 1, and provides an organic light emitting device. do.

The organic material layer of the organic light emitting device of the present invention may have a single-layer structure, but may have a multi-layer structure in which two or more organic material layers are stacked. For example, the organic light emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, an electron suppressing layer, a light emitting layer, a hole suppressing layer, an electron transport layer, an electron injection layer, etc. 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 addition, the organic material layer may include a hole injection layer, a hole transport layer, or a layer that simultaneously performs hole injection and transport, and the hole injection layer, a hole transport layer, or a layer that simultaneously performs hole injection and transport is represented by Formula 1 It includes the compound displayed.

In addition, the organic material layer may include an electron suppression layer, wherein the electron suppression layer is located adjacent to the light emitting layer, and the electron suppression layer includes a compound represented by Chemical Formula 1.

Further, the organic material layer may include a light emitting layer, and the light emitting layer includes a compound represented by Chemical Formula 1. In particular, the compound according to the present invention can be used as a dopant in a light emitting layer.

In addition, the organic material layer may include a hole suppressing layer, wherein the hole suppressing layer is located adjacent to the light emitting layer, and the hole suppressing layer includes a compound represented by Chemical Formula 1.

In addition, the organic material layer may include an electron transport layer, an electron injection layer, or a layer that simultaneously performs electron injection and transport, and the electron transport layer, an electron injection layer, or a layer that simultaneously performs electron injection and transport may be represented by Chemical Formula 1 It includes the compound displayed.

In addition, the organic material layer includes a hole transport layer and a light emitting layer, and the hole transport layer may include a compound represented by Chemical Formula 1.

In addition, the organic layer includes an electron suppressing layer and a light emitting layer, and the electron suppressing layer may include a compound represented by Chemical Formula 1.

Further, the organic light emitting device according to the present invention may be an organic light emitting device having a structure in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate. Further, the organic light emitting device according to the present invention may be an organic light emitting device of an inverted type in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate. For example, the structure of the organic light emitting device according to an embodiment of the present invention is illustrated in FIGS. 1 and 2.

FIG. 1 shows an example of an organic light emitting device including a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4. In such a structure, the compound represented by Chemical Formula 1 may be included in the light emitting layer.

FIG. 2 shows an example of an organic light emitting device comprising a substrate 1, an anode 2, a hole transport layer 5, an electron suppressing layer 6, a light emitting layer 3, an electron transport layer 7, and a cathode 4 It is done. In such a structure, the compound represented by Chemical Formula 1 may be included in one or more of the hole transport layer, the electron suppressing layer, the light emitting layer, and the electron transport layer.

3 shows a substrate 1, an anode 2, a hole injection layer 8, a hole transport layer 5, an electron suppression layer 6, a light emitting layer 3, a hole suppression layer 9, and an electron transport layer 7 And an example of an organic light-emitting device comprising the cathode 4. In such a structure, the compound represented by Formula 1 may be included in one or more of the hole injection layer, hole transport layer, electron suppression layer, light emitting layer, hole suppression layer, and electron transport layer.

The organic light emitting device according to the present invention may be manufactured by materials and methods known in the art, except that at least one layer of the organic material layer includes the compound represented by Chemical Formula 1. In addition, 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 according to the present invention may be manufactured by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate. At this time, a positive electrode is formed by depositing a metal or conductive metal oxide or an alloy thereof on a substrate using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation. Then, an organic material layer including a hole injection layer, a hole transporting layer, an electron suppressing layer, a light emitting layer, a hole suppressing layer, an electron transporting layer, etc. is formed thereon, and a material that can be used as a cathode is deposited thereon. In addition to this method, an organic light emitting device may be formed by sequentially depositing a cathode material, an organic material layer, and a cathode material on a substrate.

In addition, the compound represented by Chemical 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 application method means spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating, and the like, but is not limited to these.

In addition to this method, an organic light emitting device may be manufactured by sequentially depositing an organic material layer and a cathode material from a cathode material on a substrate (WO 2003/012890). However, the manufacturing method is not limited thereto.

In one example, the first electrode is an anode, the second electrode is a cathode, or the first electrode is a cathode, and the second electrode is an anode.

The positive electrode material is preferably a material having a large work function so that hole injection into the organic material layer is smooth. Specific examples of the positive electrode material 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; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDOT), polypyrrole, and polyaniline, but are not limited thereto.

The cathode material is preferably 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 is a multilayer structure material such as LiF / Al or LiO ₂ / Al, but is not limited thereto.

The hole injection layer is a layer for injecting holes from an electrode, and has the ability to transport holes as a hole injection material, and thus has a hole injection effect at an anode, an excellent hole injection effect for a light emitting layer or a light emitting material, and is produced in the light emitting layer. A compound which prevents migration of the excitons to the electron injection layer or the electron injection material, and which has excellent thin film formation ability is preferable. It is preferable that the highest occupied molecular orbital (HOMO) 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 the hole injection material include metal porphyrin, oligothiophene, arylamine-based organic matter, hexanitrile hexaazatriphenylene-based organic matter, quinacridone-based organic matter, and perylene-based Organic materials, anthraquinones, and polyaniline and polythiophene-based conductive polymers, but are not limited thereto.

The hole transport layer is a layer that transports holes from the hole injection layer to the light emitting layer by receiving holes, and is a material that can transport holes to the light emitting layer by receiving holes from the anode or the hole injection layer as a hole transport material and has a large mobility for holes This is suitable. Specific examples include arylamine-based organic materials, conductive polymers, and block copolymers having a conjugated portion and a non-conjugated portion, but are not limited thereto.

The electron suppressing layer is formed on the hole transport layer, specifically, the electron suppressing layer is provided in contact with the light emitting layer, and prevents excessive movement of electrons to increase the probability of hole-electron bonding, thereby improving the efficiency of the organic light emitting device It means the layer to do. The electron suppressing layer is preferably a material having a small mobility for electrons so that the electrons do not move in the light emitting layer.

As the light-emitting material, a material capable of emitting light in the visible light region by receiving and bonding holes and electrons from the hole transport layer and the electron transport layer, respectively, is preferably a material having good quantum efficiency for fluorescence or phosphorescence. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq ₃ ); Carbazole-based compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzo quinoline-metal compound; Benzoxazole, benzthiazole and benzimidazole compounds; Poly (p-phenylenevinylene) (PPV) polymers; Spiro compounds; Polyfluorene, rubrene, and the like, but are not limited to these.

The light emitting layer may include a host material and a dopant material. The host material may be a condensed aromatic ring derivative or a heterocyclic compound. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., and heterocyclic compounds include carbazole derivatives, dibenzofuran derivatives, and ladder types Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.

Examples of the dopant material include aromatic amine derivatives, strylamine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specifically, the aromatic amine derivative is a condensed aromatic ring derivative having a substituted or unsubstituted arylamino group, and includes arylamino groups such as pyrene, anthracene, chrysene, periplanten, and the substituted or unsubstituted styrylamine compound. A compound in which at least one arylvinyl group is substituted with the arylamine, a substituent selected from 1 or 2 or more from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group, and an arylamino group is substituted or unsubstituted. Specifically, styrylamine, styryldiamine, styryltriamine, styryltetraamine, and the like, but are not limited thereto. In addition, examples of the metal complex include an iridium complex and a platinum complex, but are not limited thereto.

The hole suppressing layer is formed on the light emitting layer, and specifically, the hole suppressing layer is provided in contact with the light emitting layer, thereby preventing excessive movement of holes and increasing the probability of hole-electron bonding, thereby improving the efficiency of the organic light emitting device. It means the floor. The electron suppressing layer is suitable for a material having a small mobility to the hole so that the hole does not move again in the light emitting layer.

The electron transport layer is a layer that receives electrons from the electron injection layer and transports electrons to the light emitting layer. Specifically, the electron transport layer is provided in contact with the hole inhibiting layer. Particularly, as the electron transporting material in the electron transporting layer, a material capable of receiving electrons from the cathode and transferring them to the light emitting layer is suitable. Specific examples include the Al complex of 8-hydroxyquinoline; Complexes including Alq ₃ ; Organic radical compounds; Hydroxyflavone-metal complexes, and the like, but are not limited to these. 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 those that have a low work function and are followed by an aluminum or silver layer. Specifically, cesium, barium, calcium, ytterbium and samarium, each case followed by an aluminum layer or a silver layer.

The electron injection layer is a layer that injects electrons from an electrode, has the ability to transport electrons, has an electron injection effect from a cathode, has an excellent electron injection effect on a light emitting layer or a light emitting material, and hole injection of excitons generated in the light emitting layer A compound that prevents migration to the layer and has excellent thin film forming ability is preferred. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone and the like and their derivatives, metal Complex compounds, nitrogen-containing 5-membered ring derivatives, and the like, 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) ( There are o-cresolato) gallium, bis (2-methyl-8-quinolinato) (1-naphtholato) aluminum, bis (2-methyl-8-quinolinato) (2-naphtholato) gallium, It is not limited to this.

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

In addition, the compound represented by Chemical Formula 1 may be included in an organic solar cell or an organic transistor in addition to the organic light emitting device.

The production of a novel compound according to the present invention and an organic light-emitting device comprising the same will be described in detail in the Examples below. However, the following examples are intended to illustrate the invention, and the scope of the invention is not limited by them.

Synthesis Example 1. Synthesis of Compound 1

Step 1) Synthesis of Compound 1-A

Using 2,6-dibromoaniline (50.0 g, 199.27 mmol) and [1.1'-biphenyl] -4-ylboronic acid (82.87 g, 418.46 mmol) in the same manner as in Step 1 of Synthesis Example 1 The compound 7-A (68.0 g, 85.84% yield) was obtained.

After dissolving 2,6-dibromoaniline (50.0 g, 199.27 mmol) and [1.1'-biphenyl] -4-ylboronic acid (82.87 g, 418.46 mmol) in 1,4-dioxane (700 mL), A solution of potassium carbonate (130.71 g, 996.35 mmol, 350 mL water) was added, followed by heating and stirring for 10 minutes. Bis (tri-tert-butylphosphine) palladium (BTP, 0.20 g, 0.40 mmol) dissolved in 1,4-dioxane (10 mL) was added to the solution, followed by heating and stirring for 1 hour. After completion of the reaction and filtration, layer separation was performed with chloroform and water. After removal of the solvent, recrystallization with ethyl acetate gave the compound 1-A (68.0 g, 85.84% yield).

Step 2) Synthesis of Compound 1-B

Compound 1-A (40.0 g, 100.63 mmol) obtained in Step 1 of Synthesis Example 1, bromobenzene (15.80 g, 100.63 mmol), and sodium tolu-butoxide (21.94 g, 228.27 mmol) in toluene (250) mL), followed by stirring for 10 minutes. To the mixture, 1,1'-bis (diphenylphosphino) ferrocene dichloropalladium (II) (Pd (dppf) Cl ₂ , 0.60 g, 0.82 mmol) dissolved in toluene (30 mL) was added, followed by heating for 1 hour. It was stirred. After completion of the reaction and filtration, layer separation was performed with toluene and water. After removal of the solvent, recrystallization with ethyl acetate gave the compound 1-B (37.0 g, 77.63% yield).

Step 3) Synthesis of Compound 1

Compound 1-B (20.0 g, 42.23 mmol) obtained in Step 2 of Synthesis Example 1 and 4-bromo-1,1 ': 4', 1 "-terphenyl (13.32 g, 43.07 mmol) and sodium tert -Xylene (200 mL) was added to butoxide (NaOtBu, 8.37 g, 87.11 mmol), followed by heating and stirring for 10 minutes Bis (tri-tert-butylphos) dissolved in xylene (10 mL) was added to the mixture. Pin) palladium (BTP, 0.16 g, 0.31 mmol) was added and stirred for 1 hour After completion of the reaction and filtration, the mixture was layer-separated with toluene and water After removal of the solvent, recrystallization with ethyl acetate gave compound 1 (21.0 g, 79.46% yield) (MS [M + H] + = 626).

Synthesis Example 2. Synthesis of Compound 2

Synthesis Example 1 using Compound 1-B (20.0 g, 42.23 mmol) and 3-bromo-9-phenyl-9 H -carbazole (13.88 g, 43.07 mmol) obtained in Step 2 of Synthesis Example 1 Compound 2 (21.5 g, 79.70% yield) was obtained in the same manner as in Step 3. (MS [M + H] + = 639)

Synthesis Example 3. Synthesis of Compound 3

Step 1) Synthesis of Compound 3-A

Using compound 1-A (40.0 g, 100.63 mmol) and 4-bromo-1.1'-biphenyl (23.46 g, 100.63 mmol) obtained in step 1 of Synthesis Example 1, step 2 of Synthesis Example 1 and Compound 3-A (47.7 g, 86.23% yield) was obtained in the same way.

Step 2) Synthesis of Compound 3

Step 3 of Synthesis Example 1 using Compound 3-A (20.0 g, 36.38 mmol) and 1-bromodibenzo [ b, d ] furan (9.17 g, 37.11 mmol) obtained in Step 1 of Synthesis Example 3 Compound 3 (19.5 g, 74.87% yield) was obtained in the same manner as. (MS [M + H] + = 716)

Synthesis Example 4. Synthesis of Compound 4

Step of Synthesis Example 1 using compound 3-A (20.0 g, 36.38 mmol) and 2-bromodibenzo [ b, d ] thiophene (9.77 g, 37.11 mmol) obtained in Step 1 of Synthesis Example 3 Compound 4 (20.4 g, 76.61% yield) was obtained by the same method as 3. (MS [M + H] + = 732)

Synthesis Example 5. Synthesis of Compound 5

Synthesis using compound 3-A (20.0 g, 36.38 mmol) and 2-bromo-9,9-dimethyl-9 H -fluorene (10.14 g, 37.11 mmol) obtained in step 1 of Synthesis Example 3 Compound 5 (21.7 g, 80.40% yield) was obtained in the same manner as in Step 3 of Example 1. (MS [M + H] + = 742)

Synthesis Example 6. Synthesis of Compound 6

Compound 1-A (15.0 g, 37.73 mmol) obtained in Step 1 of Synthesis Example 1, 2-bromonaphthalene (16.02 g, 77.35 mmol) and xylene in sodium tert-butoxide (16.45 g, 171.19 mmol) (200 mL) was added, followed by heating and stirring for 10 minutes. Bis (tri-tert-butylphosphine) palladium (0.25 g, 0.49 mmol) dissolved in xylene (15 mL) was added to the mixture, followed by heating and stirring for 1 hour. After completion of the reaction and filtration, layer separation was performed with toluene and water. After removal of the solvent, recrystallization with ethyl acetate gave the compound 6 (20.5 g, 83.61% yield). (MS [M + H] + = 650)

Synthesis Example 7. Synthesis of Compound 7

Using Compound 1-A (15.0 g, 37.73 mmol) and 4-bromo-1.1'-biphenyl (18.03 g, 77.35 mmol) obtained in Step 1 of Synthesis Example 1 in the same manner as in Synthesis Example 6 The compound 7 (22.5 g, 84.96% yield) was obtained. (MS [M + H] + = 702)

Synthesis Example 8. Synthesis of Compound 8

Synthesis using Compound 1-A (15.0 g, 37.73 mmol) and 2-bromo-9,9-dimethyl-9 H -fluorene (21.13 g, 77.35 mmol) obtained in Step 1 of Synthesis Example 1 Compound 8 (23.4 g, 79.30% yield) was obtained in the same manner as in Example 6. (MS [M + H] + = 782)

Synthesis Example 9. Synthesis of Compound 9

Step 1) Synthesis of Compound 9-A

Compound 9-A in the same manner as in Step 1 of Synthesis Example 1 using 2,6-dibromoaniline (50.0 g, 199.27 mmol) and naphthalene-1-ylboronic acid (71.97 g, 418.46 mmol) 52.0 g, 75.54% yield).

Step 2) Synthesis of Compound 9-B

Using compound 9-A (40.0 g, 115.79 mmol) and 4-bromo-1.1'-biphenyl (26.99 g, 115.79 mmol) obtained in step 1 of Synthesis Example 9, step 2 of Synthesis Example 1 and Compound 9-B (46.1 g, 80.00% yield) was obtained in the same way.

Step 3) Synthesis of Compound 9

Synthesis using Compound 9-B (20.0 g, 40.19 mmol) and 2-bromo-9,9-dimethyl-9 H -fluorene (11.20 g, 40.99 mmol) obtained in Step 2 of Synthesis Example 9 Compound 9 (21.8 g, 78.62% yield) was obtained in the same manner as in Step 3 of Example 1. (MS [M + H] + = 690)

Synthesis Example 10. Synthesis of Compound 10

Using the compound 9-A (15.0 g, 43.42 mmol) and 4-bromo-1.1'-biphenyl (20.75 g, 89.01 mmol) obtained in Step 1 of Synthesis Example 9 in the same manner as in Synthesis Example 6 The compound 10 (22.7 g, 80.45% yield) was obtained. (MS [M + H] + = 650)

Synthesis Example 11. Synthesis of Compound 11

Step 1) Synthesis of Compound 11-A

Compound 11-A in the same manner as in Step 1 of Synthesis Example 1 using 2,6-dibromoaniline (50.0 g, 199.27 mmol) and naphthalene-2-ylboronic acid (71.97 g, 418.46 mmol) 56.0 g, 81.35% yield).

Step 2) Synthesis of Compound 11-B

Using compound 11-A (40.0 g, 115.79 mmol) and 4-bromo-1.1'-biphenyl (26.99 g, 115.79 mmol) obtained in step 1 of Synthesis Example 11, step 2 of Synthesis Example 1 and Compound 11-B (48.3 g, 83.82% yield) was obtained by the same method.

Step 3) Synthesis of Compound 11

Synthesis using Compound 11-B (20.0 g, 40.19 mmol) obtained in Step 2 of Synthesis Example 11 and 2-bromo-9,9-dimethyl-9 H -fluorene (11.20 g, 40.99 mmol) Compound 11 (22.8 g, 82.23% yield) was obtained by the same method as in Step 3 of Example 1. (MS [M + H] + = 690)

Synthesis Example 12. Synthesis of Compound 12

Using Compound 11-A (15.0 g, 43.42 mmol) and 4-bromo-1.1'-biphenyl (20.75 g, 89.01 mmol) obtained in Step 1 of Synthesis Example 11 in the same manner as in Synthesis Example 6 The compound 12 (23.8 g, 84.35% yield) was obtained. (MS [M + H] + = 650)

Synthesis Example 13. Synthesis of Compound 13

Step 1) Synthesis of Compound 13-A

After dissolving 2-bromo-6-chloroaniline (50.0 g, 242.17 mmol) and phenylboronic acid (31.00 g, 254.27 mmol) in 1,4-dioxane (600 mL), potassium carbonate (100.41 g, 726.51 mmol): Water 300 mL) solution was added, followed by heating and stirring for 10 minutes. To the solution, 1,1'-bis (diphenylphosphino) ferrocenedichloropalladium (II) (0.89 g, 1.21 mmol) dissolved in 1,4-dioxane (50 mL) was added, followed by heating and stirring for 1 hour. After completion of the reaction and filtration, layer separation was performed with chloroform and water. After removal of the solvent, recrystallization with ethyl acetate gave the compound 13-A (40.0 g, 81.10% yield).

Step 2) Synthesis of Compound 13-B

Compound 13-A (40.0 g, 196.40 mmol) and [1.1'-biphenyl] -4-ylboronic acid (40.84 g, 206.22 mmol) obtained in Step 1 of Synthesis Example 13 were used as 1,4-dioxane (500 After dissolving in mL), a solution of potassium carbonate (81.43 g, 589.20 mmol: 250 mL of water) was added, followed by heating and stirring for 10 minutes. Bis (tri-tert-butylphosphine) palladium (0.50 g, 0.98 mmol) dissolved in 1,4-dioxane (25 mL) was added to the solution, followed by heating and stirring for 1 hour. After completion of the reaction and filtration, layer separation was performed with chloroform and water. After removal of the solvent, recrystallization with ethyl acetate gave the compound 13-B (48.0 g, 76.04% yield).

Step 3) Synthesis of Compound 13

Synthesis using Compound 13-B (15.0 g, 46.67 mmol) obtained in Step 2 of Synthesis Example 13 and 2-bromo-9,9-dimethyl-9 H -fluorene (26.13 g, 95.67 mmol) Compound 13 (26.4 g, 78.92% yield) was obtained in the same manner as in Example 6. (MS [M + H] + = 706)

Synthesis Example 14. Synthesis of Compound 14

Step 1) Synthesis of Compound 14-A

Using the compound 13-A (40.0 g, 196.40 mmol) and naphthalene-1-ylboronic acid (35.47 g, 206.22 mmol) obtained in Step 1 of Synthesis Example 13 in the same manner as in Step 2 of Synthesis Example 13 The compound 14-A (45.0 g, 77.57% yield) was obtained.

Step 2) Synthesis of Compound 14

Using the compound 14-A (15.0 g, 50.78 mmol) and 4-bromo-1.1'-biphenyl (24.27 g, 104.10 mmol) obtained in Step 1 of Synthesis Example 14 in the same manner as in Synthesis Example 6 The compound 14 (25.2 g, 82.74% yield) was obtained. (MS [M + H] + = 600)

Synthesis Example 15. Synthesis of Compound 15

Compound 14-A (15.0 g, 50.78 mmol) obtained in Step 1 of Synthesis Example 14 and 4-bromo-1,1 ': 4', 1 "-terphenyl (32.19 g, 104.10 mmol) were used. The compound 15 (30.5 g, 79.87% yield) was obtained in the same manner as in Synthesis Example 6. (MS [M + H] + = 752)

Synthesis Example 16. Synthesis of Compound 16

Step 1) Synthesis of Compound 16-A

Using the compound 13-A (40.0 g, 196.40 mmol) and naphthalene-2-ylboronic acid (35.47 g, 206.22 mmol) obtained in Step 1 of Synthesis Example 13 in the same manner as in Step 2 of Synthesis Example 13 The compound 16-A (46.0 g, 79.29% yield) was obtained.

Step 2) Synthesis of Compound 16

Using the compound 16-A (15.0 g, 50.78 mmol) and 4-bromo-1.1'-biphenyl (24.27 g, 104.10 mmol) obtained in Step 1 of Synthesis Example 16 in the same manner as in Synthesis Example 6 The compound 16 (26.0 g, 85.37% yield) was obtained. (MS [M + H] + = 600)

Synthesis Example 17. Synthesis of Compound 17

Synthesis using Compound 16-A (15.0 g, 50.78 mmol) obtained in Step 1 of Synthesis Example 16 and 2-bromo-9,9-dimethyl-9 H -fluorene (28.44 g, 104.10 mmol) Compound 17 (26.2 g, 75.89% yield) was obtained in the same manner as in Example 6. (MS [M + H] + = 680)

Synthesis Example 18. Synthesis of Compound 18

Step 1) Synthesis of Compound 18-A

The same method as in Step 1 of Synthesis Example 13 using 2-bromo-6-chloroaniline (50.0 g, 242.17 mmol) and [1.1'-biphenyl] -4-ylboronic acid (50.35 g, 254.27 mmol) The compound 18-A (52.0 g, 76.75% yield) was obtained.

Step 2) Synthesis of Compound 18-B

Using the compound 18-A (40.0 g, 142.97 mmol) and naphthalene-1-ylboronic acid (25.82 g, 150.12 mmol) obtained in Step 1 of Synthesis Example 18 in the same manner as in Step 2 of Synthesis Example 13 The compound 18-B (40.0 g, 75.31% yield) was obtained.

Step 3) Synthesis of Compound 18

Synthesis using Compound 18-B (15.0 g, 40.38 mmol) and 2-bromo-9,9-dimethyl-9 H -fluorene (22.61 g, 82.78 mmol) obtained in Step 2 of Synthesis Example 18 Compound 18 (24.8 g, 81.24% yield) was obtained in the same manner as in Example 6. (MS [M + H] + = 756)

Synthesis Example 19. Synthesis of Compound 19

Step 1) Synthesis of Compound 19-A

2-Bromo-6-chloroaniline (50.0 g, 242.17 mmol) and [1.1 ': 4', 1 "-terphenyl] -4-ylboronic acid (69.70 g, 254.27 mmol) of Synthesis Example 13 Compound 19-A (68.0 g, 78.90% yield) was obtained in the same manner as in step 1.

Step 2) Synthesis of Compound 19-B

Synthesis Example using Compound 19-A (40.0 g, 112.40 mmol) obtained in Step 1 of Synthesis Example 19 and [1,1'-biphenyl] -4-ylboronic acid (23.37 g, 118.02 mmol) Compound 19-B (40.0 g, 75.13% yield) was obtained in the same manner as in Step 2 of 13.

Step 3) Synthesis of Compound 19

Synthesis using Compound 19-B (15.0 g, 31.67 mmol) obtained in Step 2 of Synthesis Example 19 and 2-bromo-9,9-dimethyl-9 H -fluorene (15.13 g, 64.93 mmol) Compound 19 (20.1 g, 81.58% yield) was obtained in the same manner as in Example 6. (MS [M + H] + = 778)

Synthesis Example 20. Synthesis of Compound 20

Step 1) Synthesis of Compound 20-A

Using compound 19-B (40.0 g, 84.46 mmol) and 4-bromo-1.1'-biphenyl (19.69 g, 84.46 mmol) obtained in step 2 of Synthesis Example 19, step 2 of Synthesis Example 1 and In the same manner, the compound 20-A (42.0 g, 79.46% yield) was obtained.

Step 2) Synthesis of Compound 20

The compound 20-A (20.0 g, 31.96 mmol) and 2-bromo-9,9-dimethyl -9 H obtained in the above Synthesis Example 20 1 - the use of fluorene (8.90 g, 32.60 mmol) synthesized The compound 20 (19.5 g, 74.58% yield) was obtained in the same manner as in Step 3 of Example 1. (MS [M + H] + = 818)

Synthesis Example 21. Synthesis of Compound 21

Step 1) Synthesis of Compound 21-A

Using the compound 19-A (40.0 g, 112.40 mmol) obtained in Step 1 of Synthesis Example 19 and naphthalene-1-ylboronic acid (20.30 g, 118.02 mmol) in the same manner as in Step 2 of Synthesis Example 13 The compound 21-A (40.0 g, 79.51% yield) was obtained.

Step 2) Synthesis of Compound 21

Using Compound 21-A (15.0 g, 33.51 mmol) obtained in Step 1 of Synthesis Example 21 and 4-bromo-1,1 ': 3', 1 "-terphenyl (21.24 g, 68.70 mmol) The compound 21 (24.0 g, 79.21% yield) was obtained in the same manner as in Synthesis Example 6. (MS [M + H] + = 904)

Synthesis Example 22. Synthesis of Compound 22

Step 1) Synthesis of Compound 22-A

Using compound 21-A (40.0 g, 89.37 mmol) and 4-bromo-1.1'-biphenyl (20.83 g, 89.37 mmol) obtained in step 1 of Synthesis Example 21, step 2 of Synthesis Example 1 and Compound 22-A (43.0 g, 80.22% yield) was obtained in the same way.

Step 2) Synthesis of Compound 22

Step 3 of Synthesis Example 1 using Compound 22-A (20.0 g, 33.35 mmol) and 2-bromodibenzo [ b, d ] furan (8.40 g, 34.01 mmol) obtained in Step 1 of Synthesis Example 22 Compound 22 (20.0 g, 75.72% yield) was obtained in the same manner as. (MS [M + H] + = 792)

Synthesis Example 23. Synthesis of Compound 23

Step 1) Synthesis of Compound 23-A

Using the compound 19-A (40.0 g, 112.40 mmol) obtained in Step 1 of Synthesis Example 19 and naphthalene-2-ylboronic acid (20.30 g, 118.02 mmol) in the same manner as in Step 2 of Synthesis Example 13 The compound 23-A (42.0 g, 83.49% yield) was obtained.

Step 2) Synthesis of Compound 23

Same as in Synthesis Example 6 using Compound 23-A (15.0 g, 33.51 mmol) and 3-bromo-1,1'-biphenyl (16.02 g, 68.70 mmol) obtained in Step 1 of Synthesis Example 23 The compound 23 (21.0 g, 83.34% yield) was obtained by the method. (MS [M + H] + = 752)

Synthesis Example 24. Synthesis of Compound 24

The same method as in Synthesis Example 6 using Compound 23-A (15.0 g, 33.51 mmol) and 2-bromodibenzo [ b, d ] furan (16.98 g, 68.70 mmol) obtained in Step 1 of Synthesis Example 23 The compound 24 (21.0 g, 80.35% yield) was obtained. (MS [M + H] + = 780)

<Experimental Example and Comparative Experimental Example>

Experimental Example 1-1

ITO (Indium Tin Oxide) 1400 Angstrom (Å, angstrom), the thickness of the glass-coated glass substrate was placed in distilled water with detergent and washed with ultrasonic waves. At this time, Fischer (Fischer Co.) was used as the detergent, and distilled water filtered secondarily by a filter of Millipore Co. was used as the distilled water. After washing the ITO for 30 minutes, ultrasonic washing was repeated for 2 minutes with distilled water for 10 minutes. After washing with distilled water, ultrasonic cleaning was performed with a solvent of isopropyl alcohol, acetone, and methanol, followed by drying and transporting to a plasma cleaner. In addition, the substrate was washed for 5 minutes using oxygen plasma, and then transferred to a vacuum evaporator.

On the ITO transparent electrode thus prepared, a compound represented by the following chemical formula HAT was thermally vacuum-deposited to a thickness of 100 을 to form a hole injection layer. Then, a compound represented by the following Chemical Formula HT1 was vacuum-deposited to a thickness of 1150 정 as a hole transport layer, and then the compound 1 prepared in Synthesis Example 1 was thermally vacuum-deposited to a thickness of 150 으로 as an electron suppressing layer. Subsequently, a compound represented by the following Chemical Formula BH and a compound represented by the following Chemical Formula BD as a light emitting layer were vacuum-deposited to a thickness of 200 MPa at a weight ratio of 25: 1. Subsequently, the compound represented by the following formula HB1 as a hole suppressing layer was vacuum-deposited to a thickness of 50 Pa. Subsequently, the compound represented by the following Chemical Formula ET1 and the compound represented by the following LiQ were thermally vacuum-deposited to a thickness of 310 MPa at a weight ratio of 1: 1 as a layer that simultaneously performs electron transport and electron injection. An organic light emitting device was manufactured by sequentially depositing lithium fluoride (LiF) to a thickness of 12 와 and aluminum to a thickness of 1000 위에 on the electron transport and electron injection layer to form a cathode.

Experimental Examples 1-2 to 1-15 and Comparative Experimental Examples 1-1 to 1-8

Experimental Examples 1-2 to 1-15 and Comparative Experimental Example 1-1 were used in the same manner as in Experimental Example 1-1, except that the compound shown in Table 1 below was used instead of Compound 1 in Experimental Example 1-1. Organic light emitting devices of 1 to 8 were prepared. When a current of 10 mA / cm ² was applied to the organic light emitting device manufactured in Experimental Example and Comparative Experimental Example, voltage, efficiency, color coordinates, and lifetime were measured and the results are shown in Table 1 below. On the other hand, T95 means the time required for the luminance to decrease from the initial luminance (6000 nit) to 95%.

In Table 1, the compounds EB1 to EB8 used in the electron suppressing layer are represented by the following formulas EB1 to EB8, respectively.

Electronic suppression layer Voltage (V, @ 10mA / cm ² ) Efficiency (cd / A, @ 10mA / cm ² ) Color coordinate
(x, y) life span
(T95, hr) Experimental Example 1-1 Compound 1 3.54 6.15 0.141, 0.043 285 Experimental Example 1-2 Compound 3 3.52 6.10 0.143, 0.044 275 Experimental Example 1-3 Compound 5 3.51 6.15 0.141, 0.043 280 Experimental Example 1-4 Compound 6 3.50 6.21 0.139, 0.045 290 Experimental Example 1-5 Compound 7 3.48 6.24 0.139, 0.043 290 Experimental Example 1-6 Compound 10 3.48 6.26 0.141, 0.043 295 Experimental Example 1-7 Compound 12 3.47 6.27 0.141, 0.043 285 Experimental Example 1-8 Compound 14 3.59 6.18 0.142, 0.044 280 Experimental Example 1-9 Compound 15 3.54 6.17 0.141, 0.045 270 Experimental Example 1-10 Compound 16 3.53 6.14 0.142, 0.043 280 Experimental Example 1-11 Compound 19 3.52 6.22 0.141, 0.043 285 Experimental Example 1-12 Compound 21 3.54 6.24 0.142, 0.043 275 Experimental Example 1-13 Compound 22 3.50 6.20 0.142, 0.044 280 Experimental Example 1-14 Compound 23 3.54 6.26 0.141, 0.043 275 Experimental Example 1-15 Compound 24 3.53 6.21 0.142, 0.044 280 Comparative Experimental Example 1-1 EB1 3.86 5.73 0.143, 0.046 235 Comparative Experimental Example 1-2 EB2 4.18 5.25 0.144, 0.048 180 Comparative Experimental Example 1-3 EB3 4.00 5.55 0.143, 0.047 220 Comparative Experimental Example 1-4 EB4 4.05 5.48 0.143, 0.048 210 Comparative Experimental Example 1-5 EB5 4.01 5.40 0.144, 0.046 215 Comparative Experimental Example 1-6 EB6 4.11 5.28 0.144, 0.047 190 Comparative Experimental Example 1-7 EB7 4.20 5.40 0.144, 0.047 180 Comparative Experimental Example 1-8 EB8 4.30 5.10 0.143, 0.048 160

As shown in Table 1, it was confirmed that the compound of the present invention has excellent electron suppression ability, and the organic light emitting device using it as an electron suppressing layer exhibits remarkable effects in terms of driving voltage, efficiency, and life.

Experimental Examples 2-1 to 2-15 and Comparative Experimental Examples 1-1, 2-1 to 2-7

Except for using the compound represented by Formula EB1 instead of Compound 1 as the electron suppressing layer in Experimental Example 1-1, and using the compound shown in Table 2 below instead of the compound represented by Formula HT1 as the hole transport layer, The organic light emitting devices of Experimental Examples 2-1 to 2-15 and Comparative Experimental Examples 2-1 to 2-7 were manufactured in the same manner as in Experimental Example 1-1. When a current of 10 mA / cm ² was applied to the organic light emitting device manufactured in Experimental Example and Comparative Experimental Example, voltage, efficiency, color coordinates, and lifetime were measured and the results are shown in Table 1 below. On the other hand, T95 means the time required for the luminance to decrease from the initial luminance (6000 nit) to 95%.

In Table 2, the compounds HT1 to HT8 used in the hole transport layer are represented by the following formulas HT1 to HT8, respectively.

Hole transport layer Voltage (V, @ 10mA / cm ² ) Efficiency (cd / A, @ 10mA / cm ² ) Color coordinate
(x, y) life span
(T95, hr) Experimental Example 2-1 Compound 2 3.53 6.24 0.142, 0.044 275 Experimental Example 2-2 Compound 4 3.54 6.23 0.142, 0.045 285 Experimental Example 2-3 Compound 5 3.50 6.20 0.142, 0.044 270 Experimental Example 2-4 Compound 8 3.46 6.18 0.141, 0.043 290 Experimental Example 2-5 Compound 9 3.50 6.19 0.141, 0.044 285 Experimental Example 2-6 Compound 11 3.51 6.18 0.142, 0.044 285 Experimental Example 2-7 Compound 13 3.44 6.10 0.140, 0.043 270 Experimental Example 2-8 Compound 15 3.54 6.24 0.142, 0.045 290 Experimental Example 2-9 Compound 17 3.42 6.15 0.139, 0.044 280 Experimental Example 2-10 Compound 18 3.43 6.15 0.140, 0.043 275 Experimental Example 2-11 Compound 19 3.51 6.19 0.142, 0.043 285 Experimental Example 2-12 Compound 20 3.46 6.14 0.142, 0.044 280 Experimental Example 2-13 Compound 21 3.47 6.18 0.140, 0.043 275 Experimental Example 2-14 Compound 22 3.52 6.19 0.142, 0.044 280 Experimental Example 2-15 Compound 24 3.48 6.20 0.140, 0.044 275 Comparative Experimental Example 1-1 HT1 3.86 5.73 0.143, 0.046 235 Comparative Experimental Example 2-1 HT2 3.95 5.62 0.144, 0.047 220 Comparative Experimental Example 2-2 HT3 4.06 5.45 0.144, 0.047 215 Comparative Experimental Example 2-3 HT4 4.14 5.34 0.144, 0.048 200 Comparative Experimental Example 2-4 HT5 4.18 5.48 0.144, 0.048 200 Comparative Experimental Example 2-5 HT6 4.15 5.45 0.143, 0.048 205 Comparative Experimental Example 2-6 HT7 4.20 5.15 0.144, 0.048 180 Comparative Experimental Example 2-7 HT8 4.18 5.10 0.144, 0.048 170

As shown in Table 2, it was confirmed that the compound of the present invention has excellent hole transporting ability, and thus the organic light emitting device using it as a hole transport layer exhibits remarkable effects in terms of driving voltage, efficiency, and life.

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

Claims (9)

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

In Chemical Formula 1,
Ar ₁ and Ar ₂ are each independently C _6-60 aryl; Or a substituted or unsubstituted C _5-60 heteroaryl containing any one or more heteroatoms selected from the group consisting of N, O and S,
Ar ₃ and Ar ₄ are each independently C _6-60 aryl, provided that at least one of Ar ₃ and Ar ₄ is biphenylyl or naphthyl.
According to claim 1,
Ar ₁ and Ar ₂ are each independently C _6-30 aryl; Or a substituted or unsubstituted C _5-30 heteroaryl containing any one or more heteroatoms selected from the group consisting of N, O and S,
compound.
According to claim 1,
Ar ₁ and Ar ₂ are each independently phenyl, biphenylyl, terphenylyl, quarterphenylyl, naphthyl, phenanthrenyl, triphenylenyl, dimethylfluorenyl, diphenylfluorenyl, dibenzofuranyl , Dibenzothiophenyl, 9-phenyl-9H-carbazolyl, phenyl substituted with naphthyl, phenyl substituted with phenanthrenyl, or phenyl substituted with triphenylenyl,
compound.
According to claim 1,
Ar ₃ and Ar ₄ are each independently C _6-30 aryl,
compound.
According to claim 1,
Ar ₃ and Ar ₄ are each independently phenyl, biphenylyl, terphenylyl, or naphthyl,
compound.
According to claim 1,
The compound represented by Formula 1, is represented by any one of the following Formulas 1-1 to 1-12,
compound:
[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

[Formula 1-5]

[Formula 1-6]

[Formula 1-7]

[Formula 1-8]

[Formula 1-9]

[Formula 1-10]

[Formula 1-11]

[Formula 1-12]

In Chemical Formulas 1-1 to 1-12,
Ar ₁ and Ar _-2 are as defined in claim 1,
R ₁ , R ₂ , R ₃ , R ₄ , and R ₅ are each independently hydrogen, deuterium, halogen group, nitrile group, silyl group, C _6-60 aryl, C _6-60 aralkyl, C _6-60 Aralkenyl; Or a substituted or unsubstituted C _5-60 heteroaryl containing any one or more heteroatoms selected from the group consisting of N, O and S.
According to claim 4,
R ₁ , R ₂ , R ₃ , R ₄ , and R ₅ are hydrogen,
compound.
According to claim 1,
The compound represented by Formula 1 is any one selected from the group consisting of,
compound:

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 layer of the organic material layer includes the compound according to any one of claims 1 to 8. That is, an organic light emitting device.

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