WO2019078700A1 - Compound and organic light emitting device comprising same - Google Patents

Abstract

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

Description

Compounds and organic light emitting devices containing them

The present application claims the benefit of priority based on Korean Patent Application No. 10-2017-0136499 filed with the Korean Intellectual Property Office on October 20, 2017, and all contents disclosed in the Korean patent application are incorporated herein by reference .

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a compound and an organic light emitting device including the same.

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 couple to each other in the organic thin film and form a pair, which then extinguishes and emits light. The organic thin film may be composed of a single layer or a multilayer, if necessary.

In general, organic light emission phenomenon refers to a phenomenon in which an organic material is used to convert electric energy into light energy. An organic light emitting device using an organic light emitting phenomenon generally has a structure including an anode, a cathode, and an organic material layer therebetween. Here, in order to increase the efficiency and stability of the organic light emitting device, the organic material layer may have a multi-layer structure composed of different materials and may include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer. When a voltage is applied between the two electrodes in the structure of such an organic light emitting device, holes are injected in the anode, electrons are injected into the organic layer in the cathode, excitons are formed when injected holes and electrons meet, When it falls back to the ground state, the light comes out.

Development of new materials for such organic light emitting devices has been continuously required.

Nitrogen ring compounds and organic light emitting devices containing them are described in this specification.

An embodiment of the present invention provides a compound represented by the following formula (1).

[Chemical Formula 1]

In Formula 1,

R1 and R2 are each independently selected from the group consisting of hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group,

Ar 1 and Ar 2 are each independently a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group,

a and b are each independently an integer of 0 to 4,

c is an integer of 1 to 4,

a + b is 1 or more,

When a or b is 2 or more, the substituents in parentheses are the same or different from each other.

According to an embodiment of the present invention, there is also provided a plasma display panel comprising: a first electrode; A second electrode facing the first electrode; And at least one organic compound layer disposed between the first electrode and the second electrode, wherein at least one of the organic compound layers includes a compound represented by Formula 1 do.

The compound described in this specification can be used as a material of an organic layer of an organic light emitting device. The compound according to at least one embodiment can improve the efficiency, lower driving voltage and / or lifetime characteristics in the organic light emitting device. In particular, the compounds described herein can be used as hole injecting, hole transporting, hole injecting and hole transporting, electron suppressing, luminescence, hole blocking, electron transporting, or electron injecting materials.

More specifically, the compound according to one embodiment of the present invention has a structure having a high electron accepting ability and is excellent in heat resistance, so that an appropriate deposition temperature can be maintained in the production of an organic light emitting device. In addition, since the sublimation temperature is high, it is possible to achieve high purity by the sublimation purification method, and does not cause contamination of the vapor deposition film forming apparatus or the organic light emitting device in manufacturing the organic light emitting device.

Fig. 1 shows an example of an organic light-emitting device comprising 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 element comprising a substrate 1, an anode 2, a hole injecting layer 5, a hole transporting layer 6, a light emitting layer 7, an electron transporting layer 8 and a cathode 4 It is.

3 is a graph for confirming the synthesis of a compound according to one embodiment of the present invention.

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

The present invention provides a compound represented by the above formula (1). The compound represented by the following formula (1) has a small energy difference between the triplet and the singlet, so that the exciton migration (RISC) from the triplet to the singlet occurs efficiently. Therefore, When used for an organic material layer, not only the efficiency of the organic light emitting device is improved, but also a low driving voltage and an excellent lifetime characteristic.

In this specification, when a part is referred to as " including " an element, it is to be understood that it may include other elements as well, without departing from the other elements unless specifically stated otherwise.

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

In the present specification,

Quot; means a moiety bonded to another substituent or compound.

Examples of substituents herein 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 substituted position is not limited as long as the substituent is a substitutable position, , Two or more substituents may be the same as or different from each other.

As used herein, the term " substituted or unsubstituted " A halogen group; Cyano; Silyl group; Boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aryl group; And a substituted or unsubstituted heterocyclic group, or that at least two of the substituents exemplified above are substituted with a substituent to which they are linked, or have no substituent. For example, " a substituent to which at least two 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 in which two phenyl groups are connected.

Illustrative examples of such substituents are set forth below, but are not limited thereto.

In this specification, examples of the halogen group include fluorine (F), chlorine (Cl), bromine (Br) or iodine (I).

In the present specification, the silyl group may be represented by the formula of -SiR _a R _b R _c , wherein R _a , R _b and R _c are each hydrogen; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group. The silyl group specifically includes a trimethylsilyl group (TMS), a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, But is not limited thereto.

In the present specification, the boron group may be represented by the formula of -BR _d R _e , wherein R _d and R _e are each hydrogen; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group. The boron group specifically includes, but is not limited to, a trimethylboron group, a triethylboron group, a t-butyldimethylboron group, a triphenylboron group, and a phenylboron group.

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 40. According to one embodiment, the alkyl group has 1 to 20 carbon atoms. According to another embodiment, the alkyl group has 1 to 10 carbon atoms. According to another embodiment, the alkyl group has 1 to 6 carbon atoms. Specific examples of the alkyl group include a methyl group, an ethyl group, a propyl group, an n-propyl group, an isopropyl group, a butyl group, a n-butyl group, an isobutyl group, Hexyl group, 1-methylpentyl group, 2-methylpentyl group, 4-tert-butylpentyl group, 1-methylbutyl group, Methyl-2-pentyl group, 3,3-dimethylbutyl group, 2-ethylbutyl group, heptyl group, n-heptyl group, 1-methylhexyl group, cyclopentylmethyl group, cyclohexylmethyl group, octyl group, ethylhexyl group, 1-ethylhexyl group, 2-propylpentyl group, n-nonyl group, 2,2-dimethylheptyl group, Propyl group, isohexyl group, 4-methylhexyl group, 5-methylhexyl group, and the like, but are not limited thereto.

In the present specification, the alkoxy group may be linear, branched or cyclic. The number of carbon atoms of the alkoxy group is not particularly limited, but it is 1 to 40 carbon atoms and, according to one embodiment, has 1 to 20 carbon atoms. Specific examples include methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, N-hexyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, But is not limited thereto.

Substituents comprising the alkyl groups, alkoxy groups and other alkyl moieties described herein include both straight chain and branched forms.

In the present specification, the alkenyl group may be straight-chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another 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, Butenyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, (Diphenyl-1-yl) vinyl-1-yl, stilbenyl, stilenyl, and the like.

In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms. According to one embodiment, the cycloalkyl group has 3 to 40 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specific examples include cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like, but are not limited thereto.

In the present specification, the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to one embodiment, the aryl group has 6 to 20 carbon atoms. The aryl group may be a phenyl group, a biphenyl group, a terphenyl group or the like as the monocyclic aryl group, but is not limited thereto. Examples of the polycyclic aryl group include, but are not limited to, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, a perylenyl group, a triphenyl group, a klycenyl group and a fluorenyl group.

In the present specification, a fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure.

When the fluorenyl group is substituted,

,

, A spirofluorenyl group

(9,9-dimethylfluorenyl group), and

(9,9-diphenylfluorenyl group), and the like. However, the present invention is not limited thereto.

In the present specification, the heterocyclic group is a heterocyclic group and is a heterocyclic group containing at least one of N, O, P, S, Si and Se. The number of carbon atoms is not particularly limited, but is preferably 2 to 60 carbon atoms. According to one embodiment, the number of carbon atoms of the heterocyclic group is 2 to 30. Examples of the heterocyclic group include a pyridyl group, a pyrrolyl group, a pyrimidyl group, a pyridazinyl group, a furanyl group, a thiophenyl group, an imidazole group, a pyrazole group, an oxazole group, an isoxazole group, a thiazole group, A thiadiazole group, a thiadiazole group, a tetrazolyl group, a pyranyl group, a thiopyranyl group, a pyrazinyl group, an oxazinyl group, a thiazinyl group, a dioxinyl group, a triazinyl group, a tetrazinyl group, A phenanthridinyl group, a diazanaphthalenyl group, a triazinylidene group, an indole group, a thiazolidinyl group, a thiomorpholinyl group, a thiomorpholinyl group, a thiomorpholinyl group, an isothiazolyl group, , Indolinyl group, indolizinyl group, phthalazinyl group, pyridopyrimidinyl group, pyridopyrazinyl group, pyrazinopyrazinyl group, benzothiazole group, benzoxazole group, benzimidazole group, benzothiophene group , Benzofuranyl group, dibenzothiophenyl group, dibenzofuranyl , A carbazole group, a benzocarbazole group, a dibenzocarbazole group, an indolocarbazole group, an indenocarbazole group, a phenazinyl group, an imidazopyridine group, a phenoxazinyl group, a phenanthroline group, a phenanthroline group, Phenothiazine group, imidazopyridine group, imidazophenanthridine group. A benzoimidazoquinazoline group, a naphthobenzofuran group, or a benzoimidazophenanthridine group, but the present invention is not limited thereto.

In the present specification, the hydrocarbon ring may be an aromatic, aliphatic or aromatic and aliphatic condensed ring, and may be selected from the examples of the cycloalkyl group or the aryl group except the univalent hydrocarbon ring.

In the present specification, the explanation about the aryl group except for the monovalent aromatic hydrocarbon ring can be applied.

In the present specification, the formula (1) may be represented by the following formula (2).

(2)

In Formula 2,

R1, R2, Ar1, Ar2 and c are as defined in the formula (1).

Further, in one embodiment of the present specification, R 1 and R 2 are each independently a substituted or unsubstituted aryl group.

In one embodiment of the present invention, R 1 and R 2 are each independently a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.

In one embodiment of the present invention, R 1 and R 2 are each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In one embodiment of the present invention, R 1 and R 2 are each independently a substituted or unsubstituted aryl group having 6 to 12 carbon atoms.

In one embodiment of the present invention, R 1 and R 2 are each independently a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group or a substituted or unsubstituted naphthyl group.

In one embodiment of the present invention, R 1 and R 2 are each independently a substituted or unsubstituted phenyl group; Or a substituted or unsubstituted biphenyl group.

In one embodiment of the present specification, Ar1 and Ar2 each independently represent a substituted or unsubstituted heterocyclic group.

In one embodiment of the present specification, Ar1 and Ar2 each independently represent a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.

Further, in one embodiment of the present specification, Ar1 and Ar2 each independently represent a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

Further, in one embodiment of the present specification, Ar1 and Ar2 each independently represent a substituted or unsubstituted heterocyclic group having 2 to 15 carbon atoms.

Further, in one embodiment of the present specification, Ar1 and Ar2 each independently represent a substituted or unsubstituted carbazole group.

In one embodiment of the present invention, c in Formula 1 is an integer of 1 to 4, meaning that at least one cyano group is substituted.

In an embodiment of the present invention, each of a and b is independently an integer of 1 to 4.

Also, in one embodiment of the present specification, a and b are 1.

Also, in one embodiment of the present specification, c is 1 or 2.

In one embodiment of the present invention, the formula (1) may be represented by any one of the following structures.

The conjugation length of the compound and the energy band gap are closely related. Specifically, the longer the conjugation length of the compound, the smaller the energy bandgap.

In the present invention, the HOMO and LUMO energy levels of the compound can be controlled by introducing the core structure having the above structure.

Further, by introducing various substituents into the core structure having the above structure, it is possible to synthesize a compound having the intrinsic characteristics of the substituent introduced. For example, by introducing a substituent mainly used in a hole injecting layer material, a hole transporting material, a light emitting layer material, and an electron transporting layer material used in manufacturing an organic light emitting device into the core structure, a material meeting the requirements of each organic layer is synthesized .

Further, the organic light emitting device according to the present invention includes a first electrode; A second electrode facing the first electrode; And at least one organic compound layer disposed between the first electrode and the second electrode, wherein at least one of the organic compound layers includes the compound of Formula 1.

The organic light emitting device of the present invention can be manufactured by a conventional method and material for manufacturing an organic light emitting device, except that one or more organic compound layers are formed using the above-described compounds.

The compound may be formed into an organic material layer by a solution coating method as well as a vacuum deposition method in the production of an organic light emitting device. Here, the solution coating method refers to spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating, and the like, but is not limited thereto.

The organic material layer of the organic light emitting device of the present invention may have a single layer structure, but may have a multilayer 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 injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, and an electron injecting layer 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 organic light emitting device of the present invention, the organic material layer may include an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer may include a compound represented by the above formula (1).

In the organic light emitting device of the present invention, the organic material layer may include a hole injecting layer or a hole transporting layer, and the hole injecting layer or the hole transporting layer may include the compound represented by the above formula (1).

In another embodiment, the organic layer includes a light-emitting layer, and the light-emitting layer includes a compound represented by the general formula (1).

According to another embodiment of the present invention, the organic layer includes a light emitting layer, and the light emitting layer may include the compound represented by Formula 1 as a dopant in the light emitting layer.

As another example, the organic material layer may include a light emitting layer, the light emitting layer may include a compound represented by Formula 1 as a dopant, and may include a fluorescent host or a phosphorescent host. The dopant may be 100 parts by weight May be 1 to 50 parts by weight. When the content of the dopant satisfies the above range, it is possible to manufacture an organic light emitting device having high efficiency and long life characteristics by transferring triplet energy to a singlet energy.

Also, the compound of Formula 1 may be used as a thermally activated delayed fluorescence (TADF), and the compound of Formula 1 may have a DELTA E _st value of retarded fluorescence of less than 0.2 eV and an orientation factor characteristic of more than 0.7 It is possible to realize an organic light emitting device capable of emitting light of a high luminance, having a low driving voltage, and having a long life span.

The thermally activated delayed fluorescence means a phenomenon in which transit transition is induced from triplet excited state to singlet excited state due to heat energy and exciton of singlet excited state moves to the ground state to cause fluorescence emission . In addition,? E _st means the absolute value of singlet energy - triplet energy.

In one embodiment of the present invention, the organic layer includes a light-emitting layer, the light-emitting layer includes a compound represented by Formula 1 as a dopant, a fluorescent host or a phosphorescent host, have. The dopant content may be 1 to 50 parts by weight based on 100 parts by weight of the host, and the fluorescent emitter may be 0 to 10 parts by weight based on 100 parts by weight of the host.

In addition, when the light emitting layer further includes a fluorescent emitter, the compound represented by Formula 1 transmits an exciton energy to the fluorescent emitter and causes a luminescence phenomenon in the fluorescent emitter, so that it is possible to emit a high luminance, It is possible to manufacture an organic light emitting device having low and long lifetime characteristics.

As the fluorescent emitter, fluorescent materials such as an anthracene-based compound, a pyrene-based compound, and a boron-based compound may be used, but the present invention is not limited thereto.

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

According to another embodiment, the first electrode is a cathode and the second electrode is a cathode.

The structure of the organic light emitting device of the present invention may have a structure as shown in FIGS. 1 and 2, but the present invention is not limited thereto.

1 illustrates the structure of an organic light emitting device in which an anode 2, a light emitting layer 3, and a cathode 4 are sequentially laminated on a substrate 1. In FIG. In such a structure, the compound may be included in the light emitting layer (3).

2 shows an organic light emitting device in which an anode 2, a hole injecting layer 5, a hole transporting layer 6, a light emitting layer 7, an electron transporting layer 8 and a cathode 4 are sequentially laminated on a substrate 1 Structure is illustrated. In such a structure, the compound may be included in the hole injecting layer 5, the hole transporting layer 6, the light emitting layer 7, or the electron transporting layer 8.

For example, the organic light emitting device according to the present invention may be formed by using a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation to form a metal oxide or a metal oxide having conductivity on the substrate, To form an anode, an organic material layer including a hole injection layer, a hole transporting layer, a light emitting layer, and an electron transporting layer is formed on the anode, and a material which can be used as a cathode is deposited thereon. In addition to such a 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.

The organic material layer may have a multi-layer structure including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer, but is not limited thereto and may have a single layer structure. The organic material layer may be formed using a variety of polymeric materials by a method such as a solvent process such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, Layer.

As the anode material, a material having a large work function is preferably used so that hole injection can be smoothly conducted into the organic material layer. Specific examples of the cathode 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); ZnO: Al or SnO _2: a combination of a metal and an oxide such as Sb; A conductive polymer such as poly (3-methyl) compound, poly [3,4- (ethylene-1,2-dioxy)] (PEDT) compound and polypyrrole and polyaniline.

The negative electrode 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; Layer structure materials such as LiF / Al or LiO ₂ / Al, but are not limited thereto.

As the hole injecting material, it is preferable that the highest occupied molecular orbital (HOMO) of the hole injecting material is between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of the hole injecting material include metal porphyrine, oligothiophene, arylamine-based organic materials, hexanitrile hexaazatriphenylene-based organic materials, quinacridone-based organic materials, perylene , An anthraquinone, and a conductive polymer of polyaniline and a poly-compound, but the present invention is not limited thereto.

As the hole transporting material, a material capable of transporting holes from the anode or the hole injecting layer to the light emitting layer and having high mobility to holes is suitable. Specific examples include arylamine-based organic materials, conductive polymers, and block copolymers having a conjugated portion and a non-conjugated portion together, but are not limited thereto.

The light emitting layer may emit red, green or blue light, and may be formed of a phosphor or a fluorescent material. The light emitting material is preferably a material capable of emitting light in the visible light region by transporting and receiving holes and electrons from the hole transporting layer and the electron transporting layer, respectively, and 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-hydroxybenzoquinoline-metal compounds; Compounds of the benzoxazole, benzothiazole and benzimidazole series; Polymers of poly (p-phenylenevinylene) (PPV) series; Spiro compounds; Polyfluorene, rubrene, and the like, but are not limited thereto.

Examples of the host material of the light emitting layer include a condensed aromatic ring derivative or a heterocyclic compound. Specific examples of the condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds. Examples of the heterocycle-containing compounds include carbazole derivatives, dibenzofuran derivatives, Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.

Further, in one embodiment of the present specification, the above-mentioned formula (1) can be used together with the following compounds as a host material of the light emitting layer.

Examples of the dopant material include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specific examples of the aromatic amine derivatives include condensed aromatic ring derivatives having substituted or unsubstituted arylamino groups, and examples thereof include pyrene, anthracene, chrysene, and peripherrhene having an arylamino group. Examples of the styrylamine compound include substituted or unsubstituted Wherein at least one aryl vinyl group is substituted with at least one aryl vinyl group, and at least one substituent selected 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. Specific examples thereof include, but are not limited to, styrylamine, styryldiamine, styryltriamine, styryltetraamine, and the like. Examples of the metal complex include iridium complex, platinum complex, and the like, but are not limited thereto.

As the electron transporting material, a material capable of transferring electrons from the cathode well into the light emitting layer, which is suitable for electrons, is suitable. Specific examples include an Al complex of 8-hydroxyquinoline; Complexes containing Alq ₃ ; Organic radical compounds; Hydroxyflavone-metal complexes, and the like, but are not limited thereto.

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

<Production Example>

The process for preparing the material of the present invention starts from the reaction of introducing various kinds of triazine groups from a fluorophenylboronic liquid seed in which a cyano group is substituted as described below. After introducing the triazine group, biscarbazole or triscarbazole was finally introduced to synthesize the compounds of the specific examples.

Production Example 1-1: Synthesis of Compound 1-A

[Reaction Scheme 1-1]

181.9 mmol of 2-chloro-4,6-diphenyl-1,3,5-triazine and 200 mL of tetrahydrofuran were added to a solution of 30 g (181.9 mmol) of 4- (3- cyano- , 100 mL of water and heat to 60 ° C. 545.6 mmol of potassium carbonate and 1 mmol of tetrakis (triphenylphosphine) palladium were added and stirred for 3 hours under reflux. After the reaction, the reaction solution returned to room temperature was filtered to obtain a solid, and the solid was recrystallized twice with Tiechef / ethanol to obtain 57.6 g (yield: 90%) of the compound 1-A.

MS [M + H] &lt; + &gt; = 353

Production Example 1-2: Synthesis of Compound 1-B

[Reaction Scheme 1-2]

 181.9 mmol of 2-chloro-4,6-diphenyl-1,3,5-triazine and 200 mL of tetrahydrofuran were added to a solution of 30 g (181.9 mmol) of 4- (2-cyano- , 100 mL of water and heat to 60 ° C. 545.6 mmol of potassium carbonate and 1 mmol of tetrakis (triphenylphosphine) palladium were added and stirred for 3 hours under reflux. After the reaction, the reaction solution returned to room temperature was filtered to obtain a solid, and the solid was recrystallized twice with Tiechef / ethanol to obtain 55.7 g (yield: 87%) of Compound 1-B.

MS [M + H] &lt; + &gt; = 353

Production Example 1-3: Synthesis of Compound 1-C

[Reaction 1 - 3]

 (181.9 mmol), 2 - ([1,1'-biphenyl] -3-yl) -4-chloro-6-phenyl- 181.9 mmol of 3,5-triazine, 200 mL of tetrahydrofuran and 100 mL of water are mixed and heated to 60 ° C. 545.6 mmol of potassium carbonate and 1 mmol of tetrakis (triphenylphosphine) palladium were added and stirred for 3 hours under reflux. After the reaction, the reaction solution returned to room temperature was filtered to obtain a solid, and the solid was recrystallized twice with Tiechef / ethanol to obtain 71.7 g (yield: 92%) of the compound 1-C.

MS [M + H] &lt; + &gt; = 429

Production Example 1-4: Synthesis of Compound 1-D

[Reaction Scheme 1-4]

 (181.9 mmol), 2 - ([1,1'-biphenyl] -3-yl) -4-chloro-6-phenyl- 181.9 mmol of 3,5-triazine, 200 mL of tetrahydrofuran and 100 mL of water are mixed and heated to 60 ° C. 545.6 mmol of potassium carbonate and 1 mmol of tetrakis (triphenylphosphine) palladium were added and stirred for 3 hours under reflux. After the reaction, the reaction solution returned to room temperature was filtered to obtain a solid, and the solid was recrystallized twice with Tiechef / ethanol to obtain 66.2 g (yield: 85%) of compound 1-D.

MS [M + H] &lt; + &gt; = 429

Production Example 2-1: Synthesis of Compound 1

[Reaction Scheme 2-1]

1-A 15 g (42.6 mmol) of 9-phenyl-9H, 9'H-3,3'-bicarbazole (42.6 mmol) was completely dissolved in 100 mL of toluene, 63.8 mmol of sodium tert- 0.42 mmol of tetrakis triphenylphosphine palladium was added and the mixture was stirred at 80 ° C for 6 hours. The reaction mixture was concentrated under reduced pressure and the residue was purified by column chromatography with tetrahydrofuran: hexane = 1: 5 and recrystallization from toluene / ethanol (1: 1) to obtain 28.7 g of 1 %). All ratios are by weight.

MS [M + H] &lt; + &gt; = 741

Production Example 2-2: Synthesis of Compound 2

[Reaction Scheme 2-2]

1-B 15 g (42.6 mmol) of 9-phenyl-9H, 9'H-3,3'-bicarbazole (42.6 mmol) was completely dissolved in 100 mL of toluene, 63.8 mmol of sodium tert- 0.42 mmol of tetrakis triphenylphosphine palladium was added and the mixture was stirred at 80 ° C for 6 hours. After the temperature was lowered to room temperature, the salt was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography with tetrahydrofuran: hexane = 1: 5 and recrystallization from toluene / ethanol (1: 1) to obtain 28.0 g of 2 %).

MS [M + H] &lt; + &gt; = 741

Production Example 2-3: Synthesis of Compound 3

[Reaction Scheme 2-3]

1-C 18.2 g (42.6 mmol) of 9-phenyl-9H, 42.6 mmol of 9'H-3,3'-bicarbazole was completely dissolved in 100 mL of toluene, 63.8 mmol of sodium tert-butoxide was added, 0.42 mmol of tetrakis triphenylphosphine palladium was added and the mixture was stirred at 80 ° C for 6 hours. After the temperature was lowered to room temperature, the salt was removed by filtration and the filtrate was concentrated under reduced pressure. The residue was purified by recrystallization from toluene / ethanol (1: 1) by column with tetrahydrofuran: hexane = 1: 5 to obtain 30.2 g %).

MS [M + H] &lt; + &gt; = 817

Production example 2-4: Synthesis of compound 4

[Reaction Scheme 2-4]

18.2 g (42.6 mmol) of 1-D and 9-phenyl-9H, 42.6 mmol of 9'H-3,3'-bicarbazole were completely dissolved in 100 mL of toluene, 63.8 mmol of sodium tert- 0.42 mmol of tetrakis triphenylphosphine palladium was added and the mixture was stirred at 80 ° C for 6 hours. After the temperature was lowered to room temperature, the salt was removed by filtration and the filtrate was concentrated under reduced pressure. The residue was purified by recrystallization from toluene / ethanol (1: 1) and column chromatography with tetrahydrofuran: hexane = 1: 5 to obtain 29.9 g %).

MS [M + H] &lt; + &gt; = 817

Production example 2-5: Synthesis of compound 5

[Reaction Scheme 2-5]

After 15 g (42.6 mmol) of 1-A and 42.6 mmol of 9H-3,9'-bicabazole were completely dissolved in 100 mL of toluene, sodium tert-butoxide (63.8 mmol) was added thereto and tetrakis triphenylphosphine palladium mmol, and the mixture was heated and stirred at 80 ° C for 6 hours. After the temperature was lowered to room temperature, the salt was removed by filtration and the filtrate was concentrated under reduced pressure. The residue was purified by recrystallization from toluene / ethanol (1: 1) by column with tetrahydrofuran: hexane = 1: 5 to obtain 26.0 g %).

MS [M + H] &lt; + &gt; = 665

Production Example 2-6: Synthesis of Compound 7

[Reaction Scheme 2-6]

1-A 15 g (42.6 mmol), 9,9 "-diphenyl-9H, 9'H, 9''H-3,3'6'3'-teracavazole 42.6 mmol were dissolved in toluene 100 , 63.8 mmol of sodium tert-butoxide was added, and 0.42 mmol of tetrakis triphenylphosphine palladium was added thereto, followed by stirring at 80 ° C for 6 hours. The reaction mixture was concentrated under reduced pressure and the residue was purified by column chromatography with tetrahydrofuran: hexane = 1: 5 and recrystallization from toluene / ethanol (1: 1) to obtain 35.5 g (yield: 85% %).

MS [M + H] &lt; + &gt; = 982

Production example 2-7: Synthesis of compound 8

[Reaction Scheme 2-7]

1-A 15 g (42.6 mmol) of 9'H-9,3 ': 6', 9 "-tercavazole 42.6 mmol was completely dissolved in 100 mL of toluene, 63.8 mmol of sodium tert-butoxide was added , 0.42 mmol of tetrakis triphenylphosphine palladium, and the mixture was stirred at 80 ° C for 6 hours. The mixture was cooled to room temperature, filtered to remove salts, and then concentrated under reduced pressure. The residue was purified by recrystallization from toluene / ethanol (1: 1) by column chromatography with tetrahydrofuran: hexane = 1: 5 to obtain 29.3 g of 8 %).

MS [M + H] &lt; + &gt; = 830

The triazine group and the carbazoles were variously introduced through the same synthesis procedure as the above reaction formula to synthesize the substances in the specific examples.

<Experimental Example 1>

The orientation of the transient dipole moments has received much attention as one of the important factors limiting external quantum efficiency. A number of different orientation measurement methods have been used and reported in recent literature. The reported method is an angular optical luminescence profile measurement followed by an optical simulation; EEG measurement of an integral element of an EL element with / without an outcoupling lens using a device having a series of ETL thickness; And monochromatic electroluminescent far-field angle pattern measurements. All of these methods use commercial optical simulation software for data calculation and interpretation.

The methods described below are designed to evaluate the horizontal alignment factor of a number of materials used in devices having a standard set of materials.

CzTrz doped with m-CBP is deposited on a silica fused substrate made of hemispheres.

A 300 nm light which can be excited on the deposited substrate is irradiated to set a range in which the detector is positioned in a direction in which light is emitted.

Only half of the hemisphere is measured and the intensity is measured in the light.

When the horizontal ratio of the measured data is several pros, a comparison is made by simulating similarity, and then the value is confirmed.

Experimental Example  1-1

The horizontal alignment factor was measured in the same manner as in Experimental Example 1, except that Compound 8 was used instead of Compound CzTrz in Experimental Example 1.

Comparative Experimental Example 1-1

The horizontal alignment factor was measured in the same manner as in Experimental Example 1, except that BCzTrz was used in place of the compound CzTrz in Experimental Example 1.

The horizontal alignment factors measured by Experimental Example 1-1 and Comparative Example 1-1 are as shown in Table 1 below.

division	compound	Horizontal alignment factor
Experimental Example 1	CzTrz	0.66
Experimental Example 1-1	8	0.89
Comparative Example 1-1	BCzTrz	0.65

As shown in Table 1, it was confirmed that the results of Experimental Example 1-1 using Compound 8 containing cyano group had horizontal alignment factors as large as those of Experimental Example 1 and Comparative Example 1-1. As shown in Table 1 above, it was confirmed that the compound according to the present invention has a large horizontal alignment factor and thus can be applied to the organic luminescent device to realize a highly efficient organic luminescent device.

<Experimental Example 2>

In this Experimental Example, an organic light emitting device was fabricated by including the host material (m-CBP) having a triplet value of 2.5 eV or more in Formula 1 according to one embodiment of the present invention to evaluate its characteristics.

The glass substrate coated with ITO (indium tin oxide) thin film with a thickness of 1,000 Å was immersed in distilled water containing detergent and washed with ultrasonic waves. In this case, Fischer Co. was used as a detergent, and distilled water filtered by a filter of Millipore Co. was used as distilled water. The ITO was washed for 30 minutes and then washed twice with distilled water and ultrasonically cleaned for 10 minutes. After the distilled water was washed, it was ultrasonically washed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner. Further, the substrate was cleaned using oxygen plasma for 5 minutes, and then the substrate was transported by a vacuum evaporator. Each thin film was laminated on the prepared ITO transparent electrode by a vacuum deposition method with a degree of vacuum of 5.0 X 10 &lt; -4 &gt; Pa. First, hexanitrile hexaazatriphenylene (HAT) was thermally vacuum deposited on ITO to a thickness of 500 Å to form a hole injection layer.

N-phenylamino] biphenyl (NPB) (300 Å) was vacuum-deposited on the hole injection layer to form a hole transport layer, which is a material for transporting holes, and the following compound 4-4'-bis [N- (1-naphthyl) Respectively.

([1,1'-biphenyl] -4-yl) -N- (4- (11 - ([1,1'-biphenyl] -4-yl ) -11H-benzo [a] carbazole-5-yl) phenyl) - [1,1'-biphenyl] -4-amine (EB1) (100 Å) was vacuum deposited thereon to form an electron blocking layer.

Subsequently, the following m-CBP and 4CzIPN were vacuum deposited on the electron blocking layer to a thickness of 300 ANGSTROM at a weight ratio of 70:30 to form a light emitting layer.

Compound HB1 was vacuum deposited on the light emitting layer to a thickness of 100 Å to form a hole blocking layer.

Compound ET1 and compound LiQ (Lithium Quinolate) were vacuum deposited on the hole blocking layer at a weight ratio of 1: 1 to form an electron injection and transport layer having a thickness of 300 Å. Lithium fluoride (LiF) and aluminum were deposited to a thickness of 2000 Å on the electron injecting and transporting layer sequentially to form a cathode.

Was maintained at the deposition rate was 0.4 ~ 0.7Å / sec for organic material in the above process, the lithium fluoride of the cathode was 0.3Å / sec, aluminum is deposited at a rate of 2Å / sec, During the deposition, a vacuum 10 2 X ^{- 7} to 5 X 10 &lt; ^-6 &gt; torr to obtain an organic light emitting device.

Experimental Example  2-1 to 2-9

An organic light emitting device was fabricated in the same manner as in Experimental Example 2, except that the compound of Table 1 was used instead of the compound 4CzIPN in Experimental Example 2.

compare Experimental Example  2-1 to 2-2

An organic light emitting device was fabricated in the same manner as in Experimental Example 2 except that the compound of BCzTrz to TCzTrz was used in place of the compound 4CzIPN in Experimental Example 2. [

When current was applied to the organic light-emitting devices manufactured in Experimental Examples 2-1 to 2-9 and Comparative Examples 2-1 to 2-2, the results shown in the following Table 2 were obtained.

division	Compound (light emitting layer)	Voltage (V @ 10 mA / cm 2 )	Efficiency (cd / A @ 10 mA / cm 2 )	The color coordinates (x, y)
Experimental Example 2	4CzIPN	4.7	17	(0.34, 0.62)
Experimental Example 2-1	Compound 1	4.1	22	(0.33, 0.62)
EXPERIMENTAL EXAMPLE 2-2	Compound 2	4.0	21	(0.34, 0.62)
Experimental Example 2-3	Compound 3	4.1	23	(0.33, 0.61)
Experimental Example 2-4	Compound 4	4.1	23	(0.33, 0.62)
Experimental Example 2-5	Compound 5	4.1	22	(0.34, 0.61)
Experimental Examples 2-6	Compound 6	4.0	24	(0.33, 0.61)
Experimental Example 2-7	Compound 7	4.2	23	(0.33, 0.62)
Experimental Examples 2-8	Compound 8	3.9	25	(0.31, 0.63)
Experimental Examples 2-9	Compound 9	3.9	24	(0.32, 0.62)
Comparative Example 2-1	BCzTrz	4.8	16	(0.35, 0.53)
Comparative Example 2-2	TCzTrz	4.7	17	(0.37, 0.61)

As shown in Table 2, in the devices of Experimental Examples 2-1 to 2-9 using the compound having the structure of Formula 1 as the core, the voltage was lower than that of the device using the compound 4CzIPN in Experimental Example 1, Comparing with the comparative examples 2-1 to 2-2, the structure in which the cyano group is substituted with the cyano group of the formula (1) is more preferable in terms of voltage, efficiency and color purity than when the cyano group is not substituted in the core All of them were improved.

As shown in Table 1, it was confirmed that the compound of the present invention is applicable to a delayed fluorescent organic light emitting device because of its excellent light emitting ability and high color purity.

While the present invention has been particularly shown and described with reference to exemplary embodiments thereof, it is to be understood that the invention is not limited to the disclosed exemplary embodiments, but, on the contrary, is intended to cover various modifications and equivalent arrangements included within the spirit and scope of the appended claims. .

Claims (11)

1. A compound represented by the following formula (1):

   [Chemical Formula 1]

   

   In Formula 1,

   R1 and R2 are each independently selected from the group consisting of hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group,

   Ar 1 and Ar 2 are each independently a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group,

   a and b are each independently an integer of 0 to 4,

   c is an integer of 1 to 4,

   a + b is 1 or more,

   When a or b is 2 or more, the substituents in parentheses are the same or different from each other.
2. The method according to claim 1,

   Wherein the compound represented by Formula 1 is represented by Formula 2:

   (2)

   

   In Formula 2,

   R1, R2, Ar1, Ar2 and c are as defined in the formula (1).
3. The method according to claim 1,

   Lt; 1 &gt; and R &lt; 2 &gt; are each independently a substituted or unsubstituted aryl group.
4. The method according to claim 1,

   Wherein Ar1 and Ar2 each independently represent a substituted or unsubstituted carbazole group.
5. The method according to claim 1,

   Wherein c is 1 or 2.
6. The method according to claim 1,

   (1) is represented by any one of the following structures:

   

   

   

   

   

   

   .
7. A first electrode; A second electrode facing the first electrode; And at least one organic compound layer disposed between the first electrode and the second electrode, wherein at least one of the organic compound layers includes a compound according to any one of claims 1 to 6. The organic light- Light emitting element.
8. The method of claim 7,

   Wherein the organic material layer comprises a hole injection layer or a hole transport layer, and the hole injection layer or the hole transport layer comprises the compound of the formula (1).
9. The method of claim 7,

   Wherein the organic material layer comprises an electron transporting layer or an electron injecting layer, and the electron transporting layer or the electron injecting layer comprises the compound of the formula (1).
10. The method of claim 7,

    Wherein the organic layer includes a light emitting layer, and the light emitting layer comprises the compound of Formula 1.
11. [Claim 7] The organic light emitting device of claim 7, wherein the organic layer includes a light emitting layer, and the light emitting layer comprises the compound of Formula 1 as a dopant.

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