KR101964435B1 - Hetero-cyclic compound and organic light emitting device comprising the same - Google Patents

Abstract

The present invention provides a heterocyclic compound having a novel structure and an organic light emitting device comprising the heterocyclic compound.

Description

[0001] HETERO-CYCLIC COMPOUND AND ORGANIC LIGHT EMITTING DEVICE COMPRISING THE SAME [0002]

The present invention relates to a heterocyclic compound having a novel structure and an organic light emitting device including the same.

In general, organic light emission phenomenon refers to a phenomenon in which an organic material is used to convert electric energy into light energy. The organic light emitting device using the organic light emitting phenomenon has a wide viewing angle, excellent contrast, fast response time, excellent characteristics of luminance, driving voltage and response speed, and much research has been conducted.

The organic light emitting device generally has a structure including an anode and a cathode, and an organic layer between the anode and the cathode. The organic material layer may have a multilayer structure composed of different materials in order to improve the efficiency and stability of the organic light emitting device. For example, the organic material layer 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 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.

There is a continuing need for the development of new materials for the organic materials used in such organic light emitting devices.

Korean Patent Publication No. 10-2000-0051826

The present invention relates to a heterocyclic compound having a novel structure and an organic light emitting device including the same.

The present invention provides a compound represented by the following formula (1).

[Chemical Formula 1]

In Formula 1,

X is O or S,

R ₁ to R ₈ are each independently hydrogen or deuterium, at least one of R ₁ to R ₈ is deuterium, and any one of R ₁ to R ₄ is represented by the following formula (2)

(2)

Ar ₁ is substituted or unsubstituted C _10-20 aryl.

The present invention also provides a plasma display panel comprising: a first electrode; A second electrode facing the first electrode; And one or more organic layers disposed between the first electrode and the second electrode, wherein at least one of the organic layers includes a compound represented by Formula 1, to provide.

The compound represented by the general formula (1) can be used as a material of an organic material layer of an organic light emitting device and can improve the efficiency, the driving voltage and / or the lifetime of the organic light emitting device. The compound represented by the above-described formula (1) can be used as a hole injecting, hole transporting, hole injecting and transporting, luminescence, electron transporting, or electron injecting material.

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.

Hereinafter, the present invention will be described in detail in order to facilitate understanding of the present invention.

는 다른 화합물에 연결되는 결합을 의미한다. In the present specification,

Quot; refers to a bond that is linked to another compound.

In this specification the term "substituted or unsubstituted" may be substituted or means a unsubstituted by R ^a, R ^a is heavy hydrogen, a halogen, a cyano group, a nitro group, an amino group, an alkyl group having 1 to 40 carbon atoms, 1 to 40 haloalkyl groups, substituted or unsubstituted heteroalkyl groups having 1 to 40 carbon atoms containing at least one of O, N, Si and S, substituted or unsubstituted O, N, Si and S , Or an alkenyl group having 2 to 40 carbon atoms.

Halogen in this specification may be fluorine, chlorine, bromine or iodine.

In the present specification, the alkyl group having 1 to 40 carbon atoms may be a straight chain, branched chain or cyclic alkyl group. Specifically, the alkyl group having 1 to 40 carbon atoms is preferably a straight chain alkyl group having 1 to 40 carbon atoms; A straight chain alkyl group having 1 to 20 carbon atoms; A straight chain alkyl group having 1 to 10 carbon atoms; Branched or cyclic alkyl group having 3 to 40 carbon atoms; Branched or cyclic alkyl group of 3 to 20 carbon atoms; Or a branched or cyclic alkyl group having 3 to 10 carbon atoms. More specifically, the alkyl group having 1 to 40 carbon atoms is preferably a methyl group, an ethyl group, a n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a neopentyl group, a cyclohexyl group, or the like. However, the present invention is not limited thereto.

In the present specification, the heteroalkyl group having 1 to 40 carbon atoms may be one in which at least one carbon of the alkyl group is independently substituted with O, N, Si or S; Examples of the straight chain alkyl group include a n-propoxy group, a n-propoxy group, a n-propoxy group, and a heteroalkyl group substituted by Si, -Propylsilyl group, and the heteroalkyl group substituted by S is an n-propylthio group. Examples of the branched alkyl group include a heteroalkyl group in which the carbon atom of the neopentyl group is substituted by O is t-butoxy group, a heteroalkyl group substituted by N is t-butylamino group, and a heteroalkyl group substituted by Si is t Butylsilyl group, and the heteroalkyl group substituted by S is a t-butylthio group. Examples of the cyclic alkyl group include a 2-tetrahydropyranyl group in which the carbon atom of the cyclohexyl group is substituted with O is a 2-tetrahydropyranyl group, a heteroalkyl group substituted by N is a 2-piperidinyl group, The heteroalkyl group substituted by Si is a 1-sila-cyclohexyl group, and the heteroalkyl group substituted by S is a 2-tetrahydrothiopyranyl group. Specifically, the heteroalkyl group having 1 to 40 carbon atoms is preferably a straight chain, branched chain or cyclic hydroxyalkyl group having 1 to 40 carbon atoms; A linear, branched or cyclic alkoxy group having 1 to 40 carbon atoms; A linear, branched or cyclic alkoxyalkyl group having 2 to 40 carbon atoms; A straight chain, branched chain or cyclic aminoalkyl group having 1 to 40 carbon atoms; A straight chain, branched chain or cyclic alkylamino group having 1 to 40 carbon atoms; A straight chain, branched chain or cyclic alkylaminoalkyl group having 1 to 40 carbon atoms; A linear, branched or cyclic silylalkyl (oxy) group having 1 to 40 carbon atoms; A straight, branched or cyclic alkyl (oxy) silyl group having 1 to 40 carbon atoms; A straight, branched or cyclic alkyl (oxy) silylalkyl (oxy) group having 1 to 40 carbon atoms; A linear, branched or cyclic mercaptoalkyl group having 1 to 40 carbon atoms; A straight, branched or cyclic alkylthio group having 1 to 40 carbon atoms; Or a straight chain, branched chain or cyclic alkylthioalkyl group having 2 to 40 carbon atoms. More specifically, the heteroalkyl group having 1 to 40 carbon atoms is preferably a hydroxymethyl group, a methoxy group, an ethoxy group, an n-propoxy group, an iso- propoxy group, a t-butoxy group, a cycloheptoxy group, a methoxymethyl group, A 2-tetrahydropyranyl group, an aminomethyl group, a methylamino group, a n-propylamino group, a t-butylamino group, a methylaminopropyl group, a 2-piperidinyl group, a n- Butylsilyl group, a 1-sila-cyclohexyl group, a n-propylthio group, a t-butylthio group or a 2-tetrathiethylthio group. And 2-tetrahydrothiopyranyl group. However, the present invention is not limited thereto.

In the present specification, the alkenyl group having 2 to 40 carbon atoms may be a straight chain, branched chain or cyclic alkenyl group. Specifically, the alkenyl group having 2 to 40 carbon atoms is preferably a straight chain alkenyl group having 2 to 40 carbon atoms; A straight chain alkenyl group having 2 to 20 carbon atoms; A straight chain alkenyl group having 2 to 10 carbon atoms; A branched alkenyl group having 3 to 40 carbon atoms; A branched chain alkenyl group having 3 to 20 carbon atoms; A branched alkenyl group having 3 to 10 carbon atoms; A cyclic alkenyl group having 5 to 40 carbon atoms; A cyclic alkenyl group having 5 to 20 carbon atoms; Or a cyclic alkenyl group having 5 to 10 carbon atoms. More specifically, the alkenyl group having 2 to 40 carbon atoms may be an ethenyl group, a propenyl group, a butenyl group, a pentenyl group or a cyclohexenyl group. However, the present invention is not limited thereto.

The aryl group having 6 to 20 carbon atoms in the present specification may be a monocyclic aryl group or a polycyclic aryl group. Specifically, the aryl group having 6 to 20 carbon atoms may be a phenyl group, a biphenyl group, a terphenyl group, or the like as the monocyclic aryl group. Examples of the polycyclic aryl group include a naphthyl group, an anthracenyl group, a phenanthryl group, a triphenylenyl group, , A perylenyl group, a crycenyl group, a fluorenyl group, and the like.

The aryl group having 6 to 20 carbon atoms may have a structure in which two or more groups selected from the group consisting of a monocyclic aryl group and a polycyclic aryl group are connected to each other. Specifically, the aryl group having 6 to 20 carbon atoms may have a structure in which a polycyclic aryl group and / or a monocyclic aryl group is connected to a polycyclic aryl group. More specifically, the aryl group having 6 to 20 carbon atoms may be a naphthylphenyl group, an anthracenylphenyl group, a phenanthrylphenyl group, a fluorenylphenyl group, a phenylnaphthyl group, or a phenylanthracenyl group. However, the present invention is not limited thereto.

등이 될 수 있다. 다만, 이에 한정되는 것은 아니다.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,

And the like. However, the present invention is not limited thereto.

The present invention provides a compound represented by the above formula (1).

In the present invention, when the dibenzofurane or dibenzothiophene of Formula 1 is directly bonded to anthracene, the HOMO energy level of the molecule is increased and used as a host material for a light emitting layer of an organic light emitting device, So that the driving voltage is lowered. In addition, when Ar ₁ is a C _10-20 aryl group, the thermal stability is enhanced, the molecular weight is suitable for thermal vacuum deposition, and the stability in the manufacturing process of the organic light emitting device can be secured.

In addition, deuterium has a higher atomic weight than hydrogen, so that the vibration mode becomes smaller. This increases the nonradiative decay time in the excited state and, in particular, increases the stability of the triplet exciton. The increased stability of the triplet exciton can contribute to the enhancement of the efficiency and lifetime of the blue fluorescence by amplifying triplet-triplet fusion (TTF), in which singlet excitons are generated by the collision fusion of two triplet excitons.

Wherein R ₁ to R ₈ are each independently hydrogen or deuterium, at least one of R ₁ to R ₈ is deuterium, and any one of R ₁ to R ₄ is represented by the following general formula (2).

According to the bonding position of Formula 2, Formula 1 is represented by Formula 1-1, 1-2, 1-3, or 1-4:

[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

In the above Formulas 1-1 to 1-4,

X and Ar &_lt; 1 > are as defined in claim ₁ ,

In Formula 1-1, R ₁ and R ₃ to R ₈ are each independently hydrogen or deuterium, and at least one of R ₁ and R ₃ to R ₈ is deuterium,

In Formula 1-2, R ₂ to R ₈ are each independently hydrogen or deuterium, at least one of R ₂ to R ₈ is deuterium,

Wherein R ₁ , R ₂ and R ₄ to R ₈ are each independently hydrogen or deuterium, at least one of R ₁ , R ₂ and R ₄ to R ₈ is deuterium,

In Formula 1-4, R ₁ to R ₃ and R ₅ to R ₈ are each independently hydrogen or deuterium, and at least one of R ₁ to R ₃ and R ₅ to R ₈ is deuterium.

Preferably, among R &_lt; ₁ > and R < ₃ > to R < ₈ &_gt; R ₃ ; R ₄ ; R ₅ ; R ₆ ; R ₇ ; R ₈ ; R ₁ and R ₃ ; R ₆ and R ₈ ; R ₁ , R ₃ and R ₄ ; R ₅ to R ₈ ; Or R ₁ and R ₃ to R ₈ are deuterium and the remainder is hydrogen. More preferably, among R ₁ and R ₃ to R ₈ in Formula 1-1, R ₁ , R ₃ and R ₄ ; R ₅ to R ₈ ; Or R ₁ and R ₃ to R ₈ are deuterium and the remainder is hydrogen.

Also preferably, among R ₂ to R ₈ in the above formula (1-2), R ₂ ; R ₃ ; R ₄ ; R ₅ ; R ₆ ; R ₇ ; R ₈ ; R ₂ and R ₄ ; R ₆ and R ₈ ; R ₂ to R ₄ ; R ₅ to R ₈ ; Or R ₂ to R ₈ are deuterium and the remainder is hydrogen. More preferably, among R ₂ to R ₈ in the above formula (1-2), R ₂ to R ₄ ; R ₅ to R ₈ ; Or R ₂ to R ₈ are deuterium and the remainder is hydrogen.

Also preferably, among R ₁ , R ₂ and R ₄ to R ₈ of the above formula 1-3, R ₁ ; R ₂ ; R ₄ ; R ₅ ; R ₆ ; R ₇ ; R ₈ ; R ₂ and R ₄ ; R ₆ and R ₈ ; R ₁ , R ₂ and R ₄ ; R ₅ to R ₈ ; Or R ₁ , R ₂ and R ₄ to R ₈ are deuterium and the remainder is hydrogen. More preferably, among R ₁ , R ₂ and R ₄ to R ₈ of the formula 1-3, R ₁ , R ₂ and R ₄ ; R ₅ to R ₈ ; Or R ₁ , R ₂ and R ₄ to R ₈ are deuterium and the remainder is hydrogen.

Also preferably, among R ₁ to R ₃ and R ₅ to R ₈ in the general formula (1-4), R ₁ ; R ₂ ; R ₃ ; R ₅ ; R ₆ ; R ₇ ; R ₈ ; R ₁ and R ₃ ; R ₆ and R ₈ ; R ₁ to R ₃ ; R ₅ to R ₈ ; Or R ₁ to R ₃ and R ₅ to R ₈ , and the remainder is hydrogen. More preferably, among R ₁ to R ₃ and R ₅ to R ₈ in the above formula (1-4), R ₁ to R ₃ ; R ₅ to R ₈ ; Or R ₁ to R ₃ and R ₅ to R ₈ , and the remainder is hydrogen.

Preferably, Ar ₁ is naphthyl, phenylnaphthyl, phenanthrenyl, or triphenylenyl.

The compound represented by Formula 1 may be selected from the group consisting of the following compounds:

The compound represented by Formula 1-1 may be prepared according to the following Reaction Scheme 1 and may also be applied to Formulas 1, 1-2, 1-3, and 1-4.

[Reaction Scheme 1]

In the above Reaction Scheme 1, the definitions other than X 'are as defined above, and X' is halogen, more preferably bromo, or chloro.

The reaction scheme 1 is preferably carried out in the presence of a palladium catalyst and a base as a Suzuki coupling reaction, and the reactor for the Suzuki coupling reaction can be modified as known in the art. The above production method can be more specific in the production example to be described later.

Also, the present invention provides an organic light emitting device including the compound represented by Formula 1. In one embodiment, the present invention provides a liquid crystal display comprising: a first electrode; A second electrode facing the first electrode; And one or more organic layers disposed between the first electrode and the second electrode, wherein at least one of the organic layers includes a compound represented by Formula 1, to provide.

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 organic layers. However, the structure of the organic light emitting device is not limited thereto and may include a smaller number of organic layers.

The organic material layer may include a hole injecting layer, a hole transporting layer, or a layer simultaneously injecting and transporting holes, and the hole injecting layer, the hole transporting layer, And the like.

In addition, the organic layer may include a light emitting layer, and the light emitting layer may include a compound represented by the general formula (1).

The organic layer may include an electron transport layer, an electron injection layer, or a layer that simultaneously transports electrons and injects. The electron transport layer, the electron injection layer, And the like.

In addition, the organic light emitting device according to the present invention may be a normal type organic light emitting device in which an anode, one or more organic layers, and a cathode are sequentially stacked on a substrate. In addition, the organic light emitting device according to the present invention may be an inverted type organic light emitting device in which a cathode, at least one organic material layer, and an anode are sequentially stacked on a substrate. For example, the structure of an organic light emitting diode according to an embodiment of the present invention is illustrated in FIGS.

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. In such a structure, the compound represented by Formula 1 may be included in the light emitting layer.

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. In such a structure, the compound represented by Formula 1 may be contained in at least one of the hole injecting layer, the hole transporting layer, the light emitting layer, and the electron transporting layer.

The organic light emitting device according to the present invention can be manufactured by materials and methods known in the art, except that at least one of the organic material layers includes the compound represented by the above formula (1). In addition, when the organic light emitting diode includes a plurality of organic layers, the organic layers may be formed of the same material or different materials.

For example, the organic light emitting device according to the present invention can be manufactured by sequentially laminating a first electrode, an organic layer, and a second electrode on a substrate. At this time, a metal or a metal oxide having conductivity or an alloy thereof is deposited on the substrate using a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation to form an anode Forming an organic material layer including a hole injection layer, a hole transporting layer, a light emitting layer and an electron transporting layer thereon, and then depositing a material usable as a cathode on the organic material layer. In addition to such a method, an organic light emitting device can 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 Formula 1 may be formed into an organic 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, doctor blading, inkjet printing, screen printing, spraying, roll coating and the like, but is not limited thereto.

In addition to such a method, an organic light emitting device can be manufactured by sequentially depositing an organic material layer and a cathode material on a substrate from a cathode material (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 a cathode.

As the anode material, a material having a large work function is preferably used so that hole injection can be smoothly conducted to the organic material layer. 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); ZnO: Al or SNO _2: a combination of a metal and an oxide such as Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDOT), 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.

The hole injecting layer is a layer for injecting holes from an electrode. The hole injecting material has a hole injecting effect, and has a hole injecting effect on the light emitting layer or a light emitting material. A compound which prevents the migration of excitons to the electron injecting layer or the electron injecting material and is also excellent in the thin film forming ability is preferable. It is preferred that the highest occupied molecular orbital (HOMO) of the hole injecting material be 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 porphyrin, oligothiophene, arylamine-based organic materials, hexanitrile hexaazatriphenylene-based organic materials, quinacridone-based organic materials, and perylene- , Anthraquinone, polyaniline and polythiophene-based conductive polymers, but the present invention is not limited thereto.

The hole transport layer is a layer that transports holes from the hole injection layer to the light emitting layer and transports holes from the anode or the hole injection layer to the light emitting layer by using a hole transport material. 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 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.

The light emitting layer may include a host material and a dopant material. The host material is 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.

Specifically, the light-emitting layer may include the compound represented by Formula 1 as the host material. In particular, by using the compound represented by the above formula (1) as the host material of the blue light emitting layer, an organic light emitting device with excellent efficiency can be provided.

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.

The electron transporting layer is a layer that receives electrons from the electron injecting layer and transports electrons to the light emitting layer. The electron transporting material is a material capable of transferring electrons from the cathode well to the light emitting layer. 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 electron transporting layer can be used with any desired cathode material as used according to the prior art. In particular, an example of a suitable cathode material is a conventional material having a low work function followed by an aluminum layer or a silver layer. Specifically cesium, barium, calcium, ytterbium and samarium, in each case followed by an aluminum layer or a silver layer.

The electron injection layer is a layer for injecting electrons from the electrode. The electron injection layer has an ability to transport electrons, has an electron injection effect from the cathode, and has an excellent electron injection effect with respect to the light emitting layer or the light emitting material. A compound which prevents migration to a layer and is excellent in a thin film forming ability is preferable. Specific examples thereof include fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, A nitrogen-containing 5-membered ring derivative, 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- Tris (8-hydroxyquinolinato) aluminum, tris (2-methyl-8-hydroxyquinolinato) aluminum, tris (8- hydroxyquinolinato) gallium, bis (10- Quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl-8- quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) (2-naphtholato) gallium, and the like, But is 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.

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

The preparation of the compound represented by Formula 1 and the organic light emitting device comprising the same will be described in detail in the following examples. However, the following examples are intended to illustrate the present invention, and the scope of the present invention is not limited thereto.

[ Manufacturing example ]

Manufacturing example  1: Preparation of intermediate A

Dibenzo [b, d] furan-d8 (50.0 g, 283.7 mmol) was dissolved in acetic acid (500 ml) by heating under argon atmosphere. Bromine (17 ml, 340.4 mmol) was slowly added dropwise thereto, followed by stirring for 20 hours while cooling to room temperature. After the reaction was completed, the resulting solid was filtered, washed with acetic acid and water, and recrystallized from methanol to obtain Intermediate A (30.3 g, yield 42%, MS: [M + H] ⁺ = 254).

Manufacturing example  2: Preparation of intermediate B

Dibenzo [b, d] furan-d8 (50.0 g, 283.7 mmol) was dissolved in THF (500 ml) under a nitrogen atmosphere and 1.6M n-butyllithium (186 ml, 297.9 mmol) was slowly added dropwise. When the dropwise addition was completed, the solution was further stirred at -78 ° C for 1 hour. Trimethylborate (38.3 g, 368.8 mmol) was then slowly added dropwise thereto, and the mixture was stirred at room temperature for 1 hour. When the reaction was completed, 2N HCl aqueous solution (200 ml) was added dropwise at room temperature and stirred for 30 minutes. The reaction solution was transferred to a separatory funnel, and the organic layer was extracted with water and ethyl acetate. The organic layer was concentrated under reduced pressure and recrystallized from CH ₂ Cl ₂ and hexane to obtain intermediate B (29.8 g, yield 48%, MS: [M + H] < ⁺ > = 219).

Manufacturing example  3: Preparation of intermediate C

Step 1) Preparation of intermediate C-1

1,3-dimethoxybenzene-2,4,5,6-d4 (50.0 g, 351.6 mmol) was dissolved in THF (500 ml) in a nitrogen atmosphere, M n-Butyl lithium (231 ml, 369.2 mmol) was slowly added dropwise. After the dropwise addition was completed, the mixture was stirred at the same temperature for 4 hours, and then the temperature was lowered to -78 ° C. Trimethylborate (47.5 g, 457.1 mmol) was slowly added dropwise thereto and then stirred at room temperature. When the reaction was completed, 2N aqueous HCl solution was added dropwise to acidify it, followed by stirring for 30 minutes. The reaction mixture was transferred to a separatory funnel and the organic layer was extracted with water and ethyl acetate. The organic layer was concentrated under reduced pressure and recrystallized with hexane to obtain Intermediate C-1 (45.5 g, yield 70%, MS: [M ⁺ = 185).

Step 2) Preparation of intermediate C-2

A solution of Intermediate C-1 (45.0 g, 243.2 mmol) and 1-bromo-2-fluorobenzene (46.8 g, 267.6 mmol) was dissolved in THF (675 ml) and K ₂ CO ₃ (134.5 g, mmol) was dissolved in water (338 ml). Here, insert the _{Pd (PPh 3) 4 (11.2} g, 9.7 mmol), and stirred for 8 hours in an argon atmosphere under reflux conditions. After the reaction was completed, the reaction solution was cooled to room temperature, transferred to a separatory funnel, and extracted with water and ethyl acetate. The extract was dried with MgSO ₄ , filtered and concentrated. The sample was purified by silica gel column chromatography to obtain Intermediate C-2 (44.6 g, yield 78%, MS: [M + H] ⁺ = 235) .

Step 3) Preparation of intermediate C-3

Intermediate C-2 (40.0 g, 276.3 mmol), acetic acid (240 ml) and HBr (160 ml) were placed in a three-necked flask and stirred under reflux overnight. After the reaction was completed, the reaction mixture was cooled to room temperature, and water (500 ml) was added dropwise to the reaction solution. The reaction solution was then transferred to a separatory funnel, and the organic layer was extracted with water and ethyl acetate. The extract was dried over MgSO ₄ , filtered and concentrated and the sample was purified by silica gel column chromatography to give Intermediate C-3 (32.4 g, yield 92%, MS: [M + H] ⁺ = 207).

Step 4) Preparation of intermediate C-4

(30.0 g, 144.8 mmol), K ₂ CO ₃ (40.0 g, 289.5 mmol) and NMP (400 ml) were added to a three-necked flask, and the mixture was stirred overnight at 120 ° C. After the reaction was completed, the reaction mixture was cooled to room temperature, and water (500 ml) was added dropwise to the reaction solution. The reaction solution was then transferred to a separatory funnel, and the organic layer was extracted with water and ethyl acetate. The extract was dried over MgSO ₄ , filtered and concentrated and the sample was purified by silica gel column chromatography to give Intermediate C-4 (23.0 g, 85% yield, MS: [M + H] ⁺ = 187) .

Step 5) Preparation of intermediate C

The intermediate C-4 (20.0 g, 106.8 mmol) was dissolved in acetonitrile (560 ml) and then triethylamine (24 ml, 170.9 mmol) and perfluoro-1-butanesulfonyl fluoride 29 ml, 160.2 mmol), which was stirred overnight at room temperature. After the reaction was completed, the reaction mixture was diluted with ethyl acetate, transferred to a separatory funnel, washed with 0.5 M sodium bisulfate aqueous solution, and then extracted with an organic layer. The extract was dried over MgSO ₄ , filtered and concentrated and the sample was purified by silica gel column chromatography to give intermediate C (36.1 g, yield 72%, MS: [M + H] ⁺ = 469).

Manufacturing example  4: Preparation of intermediate D

Step 1) Preparation of intermediate D-1

(50.0 g, 504.3 mmol) and iodine (64.8 g, 252.2 mmol) were dissolved in distilled water (500 ml), and thereto was added a 30 wt% aqueous hydrogen peroxide solution (60 ml, 529.6 mmol) , And the mixture was stirred at 50 ° C for 24 hours. After the reaction was completed, an aqueous solution of sodium thiosulfate was added and stirred. Then, the reaction solution was transferred to a separatory funnel, and an organic layer was extracted with water and ethyl acetate. The extract was dried with MgSO ₄ , filtered and concentrated. The sample was purified by silica gel column chromatography to obtain Intermediate D-1 (54.2 g, yield 48%, MS: [M + H] ⁺ = 224) .

Step 2) Preparation of compound D-2

Intermediate D-1 (50.0 g, 223.2 mmol), NBS (41.7 g, 234.3 mmol) and DMF (1000 mL) were added to a two-necked flask and stirred at room temperature for 8 hours under an argon atmosphere. After completion of the reaction, the reaction solution was transferred to a separatory funnel, and an organic layer was extracted with water and ethyl acetate. The extract was dried over MgSO ₄ , filtered and concentrated and the sample was purified by silica gel column chromatography to give Intermediate D-2 (57.3 g, 85% yield, MS: [M + H] ⁺ = 302) .

Step 3) Preparation of intermediate D-3

(55.0 g, 182.2 mmol) and (2-fluorophenyl) boronic acid (28.0 g, 200.4 mmol) were dissolved in THF (825 ml) and K ₂ CO ₃ (100.7 g, 728.7 mmol ) Was dissolved in water (413 ml). Here, insert the _{Pd (PPh 3) 4 (8.4} g, 7.3 mmol), and stirred for 8 hours in an argon atmosphere under reflux conditions. After the reaction was completed, the reaction solution was cooled to room temperature, transferred to a separatory funnel, and extracted with water and ethyl acetate. After drying the extract with MgSO _4, then filtered and concentrated, to give a sample by column chromatography on silica gel to afford the intermediate D-3 (36.9 g, yield 75%, MS: [M + H] + = 270) .

Step 4) Preparation of intermediate D

(36.0 g, 133.3 mmol), K ₂ CO ₃ (36.8 g, 266.5 mmol) and NMP (470 ml) were added to a three-necked flask, and the mixture was stirred overnight at 120 ° C. After the reaction was completed, the reaction mixture was cooled to room temperature, and water (500 ml) was added dropwise to the reaction solution. The reaction solution was then transferred to a separatory funnel, and the organic layer was extracted with water and ethyl acetate. The extract was dried over MgSO ₄ , filtered and concentrated and the sample was purified by silica gel column chromatography to give Intermediate D (21.0 g, 63% yield, MS: [M + H] ⁺ = 250).

Manufacturing example  5: Preparation of intermediate E

Step 1) Preparation of intermediate E-1

(50.0 g, 223.2 mmol) and (5-bromo-2-fluorophenyl) boronic acid (53.7 g, 245.5 mmol) were dissolved in THF (750 ml) and K ₂ CO ₃ 123.4 g, 892.7 mmol) was dissolved in water (375 ml). Here, insert the _{Pd (PPh 3) 4 (10.3} g, 8.9 mmol), and stirred for 8 hours in an argon atmosphere under reflux conditions. After the reaction was completed, the reaction solution was cooled to room temperature, transferred to a separatory funnel, and extracted with water and ethyl acetate. The extract was dried with MgSO ₄ , filtered and concentrated. The sample was purified by silica gel column chromatography to obtain Intermediate E-1 (45.4 g, yield 75%, MS: [M + H] ⁺ = 271) .

Step 2) Preparation of intermediate E

Intermediate E-1 (45.0 g, 166.0 mmol), K ₂ CO ₃ (45.9 g, 332.0 mmol) and NMP (585 ml) were added to a three-necked flask and stirred overnight at 120 ° C. After the reaction was completed, the reaction mixture was cooled to room temperature, and water (600 ml) was added dropwise to the reaction solution. The reaction solution was then transferred to a separatory funnel, and the organic layer was extracted with water and ethyl acetate. The extract was dried over MgSO ₄ , filtered and concentrated and the sample was purified by silica gel column chromatography to give Intermediate E (25.4 g, yield 61%, MS: [M + H] ⁺ = 251).

Manufacturing example  6: Preparation of intermediate F

Dibenzo [b, d] thiophene-d8 (30.0 g, 156.0 mmol) was dissolved in acetic acid (300 ml) under argon atmosphere. Bromine (10 ml, 187.2 mmol) was slowly added dropwise thereto, followed by stirring for 20 hours while cooling to room temperature. After completion of the reaction, the resulting solid was filtered, washed with acetic acid and water, and recrystallized from methanol to obtain Intermediate F (16.0 g, yield 38%, MS: [M + H] ⁺ = 270).

[ Example ]

Example  1: Preparation of compound 1

Step 1) Preparation of compound 1-a

To the three-necked flask was added 9-bromoanthracene (15.0 g, 58.3 mmol), bis (pinacolato) diboron (17.8 g, 70.0 mmol), Pd (dba) ₂ (0.7 g, 1.2 mmol), tricyclohexylphosphine (0.7 g, 2.3 mmol), KOAc (11.5 g, 116.7 mmol) and 1,4-dioxane (225 ml) were placed and the mixture was stirred under reflux in an argon atmosphere for 12 hours. After the reaction was completed, the reaction solution was transferred to a separatory funnel, and water (200 mL) was added thereto, followed by extraction with ethyl acetate. The extract was dried with MgSO ₄ , filtered and concentrated. The sample was purified by silica gel column chromatography to give compound 1-a (14.7 g, yield 83%, MS: [M + H] ⁺ = 304) .

Step 2) Preparation of compound 1-b

(14.0 g, 46.0 mmol) and Intermediate A (12.9 g, 50.6 mmol) were dissolved in THF (210 ml) and K ₂ CO ₃ (25.4 g, 184.1 mmol) ). Here, insert the _{Pd (PPh 3) 4 (2.1} g, 1.8 mmol), and stirred for 8 hours in an argon atmosphere under reflux conditions. After the reaction was completed, the reaction solution was cooled to room temperature, transferred to a separatory funnel, and extracted with water and ethyl acetate. The extract was dried over MgSO ₄ , filtered and concentrated. The sample was purified by silica gel column chromatography to obtain Compound 1-b (12.6 g, yield 78%, MS: [M + H] ⁺ = 351) .

Step 3) Preparation of compound 1-c

Compound 1-b (12.0 g, 34.1 mmol), NBS (6.4 g, 35.9 mmol) and DMF (240 mL) were added to a two-necked flask and stirred at room temperature for 8 hours under argon atmosphere. After completion of the reaction, the reaction solution was transferred to a separatory funnel, and an organic layer was extracted with water and ethyl acetate. The extract was dried over MgSO ₄ , filtered and concentrated. The sample was purified by silica gel column chromatography to give compound 1-c (12.9 g, yield 88%, MS: [M + H] ⁺ = 403) .

Step 4) Preparation of Compound 1

Compound 1-c (12.5 g, 29.0 mmol) and naphthalene-2-ylboronic acid (5.5 g, 32.0 mmol) were dissolved in THF (190 ml) and K ₂ CO ₃ (16.1 g, 116.2 mmol) (94 ml). Here, insert the _{Pd (PPh 3) 4 (1.3} g, 1.2 mmol), and stirred for 8 hours in an argon atmosphere under reflux conditions. After the reaction was completed, the reaction solution was cooled to room temperature, transferred to a separatory funnel, and extracted with water and ethyl acetate. After drying the extract with MgSO _4, then filtered and concentrated, and then purifying the sample by column chromatography on silica gel, using a purified to give the compounds (1) Sublimation (4.9 g, yield 35%, MS: [M + H] ^{+ &} Gt ^; = 478).

Example  2: Preparation of compound 2

Compound 4 was prepared in the same manner as in the preparation of Compound 1 except that naphthalene-1-ylboronic acid was used instead of naphthalene-2-ylboronic acid in Step 4 of Example 1 (4.7 g, yield: 34% MS: [M + H] < ⁺ > = 478).

Example  3: Preparation of compound 3

Compound 3 was prepared in the same manner as in the preparation of Compound 1 except that phenanthrene-9-ylboronic acid was used instead of naphthalene-2-ylboronic acid in Step 4 of Example 1 (5.7 g, yield 37% , MS: [M + H] < ⁺ > = 528).

Example  4: Preparation of compound 4

Compound 4 was prepared in the same manner as in the preparation of Compound 1 except that (4-phenylnaphthalen-1-yl) boronic acid was used instead of naphthalene-2-ylboronic acid in Step 4 of Example 1 g, yield 32%, MS: [M + H] < ⁺ > = 554).

Example  5: Preparation of compound 5

Step 1) Preparation of compound 5-a

9-bromoanthracene (14.0 g, 54.4 mmol) and Intermediate B (13.1 g, 59.9 mmol) were dissolved in THF (210 ml) and K ₂ CO ₃ (30.1 g, 217.8 mmol) ). Here Pd (PPh ₃₎ into a ₄ (2.5g, 2.2mmol), followed by stirring for 8 hours in an argon atmosphere under reflux conditions. After the reaction was completed, the reaction solution was cooled to room temperature, transferred to a separatory funnel, and extracted with water and ethyl acetate. The extract was dried with MgSO ₄ , filtered and concentrated. The sample was purified by silica gel column chromatography to give compound 5-a (14.4 g, yield 75%, MS: [M + H] ⁺ = 351) .

Step 2) Preparation of compound 5-b

Compound 8-a (14.0 g, 39.8 mmol), NBS (7.4 g, 41.8 mmol) and DMF (280 ml) were placed in a two-necked flask and stirred at room temperature for 8 hours under argon atmosphere. After completion of the reaction, the reaction solution was transferred to a separatory funnel, and an organic layer was extracted with water and ethyl acetate. The extract was dried with MgSO ₄ , filtered and concentrated. The sample was purified by silica gel column chromatography to give 13.2 g (13.2 g, yield 77%, MS: [M + H] ⁺ = 403) .

Step 3) Preparation of compound 5

Compound 5 was prepared in the same manner as in the preparation of Compound 1, except that Compound 5-b was used instead of Compound 1-c in Step 4 of Example 1 (4.3 g, yield: 31%, MS: [M + H] < ⁺ > = 478).

Example  6: Preparation of Compound 6

Except that naphthalene-1-ylboronic acid was used instead of naphthalene-2-ylboronic acid and Compound 5-b was used in place of Compound 1-c in Step 4 of Example 1 to obtain Compound 1 Compound 6 was prepared (4.4 g, yield 32%, MS: [M + H] < ⁺ > = 478).

Example  7: Preparation of Compound 7

Except that the compound 5-b was used instead of the compound 1-c and the (6-phenylnaphthalen-2-yl) boronic acid was used instead of the naphthalene-2-ylboronic acid in the step 4 of Example 1, (5.0 g, yield 31%, MS: [M + H] < ⁺ > = 554).

Example  8: Preparation of compound 8

In the same manner as in the production of Compound 1, except for using Compound 5-b instead of Compound 1-c and using triphenylene-2-ylboronic acid instead of naphthalene-2-ylboronic acid in Step 4 of Example 1 (6.2 g, yield 37%, MS: [M + H] < ⁺ > = 578).

Example  9: Preparation of compound 9

Step 1) Preparation of compound 9-a

3-necked flask, the compound 1-a (15.0 g, 49.3 mmol), dissolved in an intermediate C (25.5 g, 54.2 mmol) in _{THF (225 ml), K 2} CO 3 (27.3 g, 197.2 mmol) water (113 ml ). Here, insert the _{Pd (PPh 3) 4 (2.3} g, 2.0 mmol), and stirred for 8 hours in an argon atmosphere under reflux conditions. After the reaction was completed, the reaction solution was cooled to room temperature, transferred to a separatory funnel, and extracted with water and ethyl acetate. The extract was dried over MgSO ₄ , filtered and concentrated. The sample was purified by silica gel column chromatography to give compound 9-a (11.6 g, yield 68%, MS: [M + H] ⁺ = 347) .

Step 2) Preparation of compound 9-b

Compound 9-b was prepared in the same manner as in the production of Compound 1-c, except that Compound 9-a was used instead of Compound 1-b in Step 3 of Example 1 (11.9 g, yield 88% MS: [M + H] < ⁺ > = 426).

Step 3) Preparation of Compound 9

Compound 9 was prepared in the same manner as in the preparation of Compound 1, except that Compound 9-b was used in place of Compound 1-c in Step 4 of Example 1 (4.3 g, yield: 34%, MS: [M + H] < ⁺ > = 474).

Example  10: Preparation of compound 10

Except that phenanthrene-9-ylboronic acid was used instead of naphthalene-2-ylboronic acid and compound 9-b was used in place of the compound 1-c in the step 4 of Example 1, (4.4 g, 31% yield, MS: [M + H] < ⁺ > = 524).

Example  11: Preparation of compound 11

Step 1) Preparation of compound 11-a

Compound 11-a was prepared in the same manner as in the preparation of Compound 1-b, except that Intermediate D was used instead of Intermediate A in Step 2 of Example 1 (11.4 g, yield: 71%, MS: [M + H] < ⁺ > = 347).

Step 2) Preparation of compound 11-b

Compound 11-b was prepared in the same manner as in the preparation of Compound 1-c, except that Compound 11-a was used instead of Compound 1-b in Step 3 of Example 1 (11.5 g, yield 85% MS: [M + H] < ⁺ > = 426).

Step 3) Preparation of compound 11

Compound 11 was prepared in the same manner as in the preparation of Compound 1, except that Compound 11-b was used instead of Compound 1-c in Step 4 of Example 1 (4.5 g, yield 35%, MS: [M + H] < ⁺ > = 474).

Example  12: Preparation of compound 12

Except that naphthalene-1-ylboronic acid was used instead of naphthalene-2-ylboronic acid and Compound 11-b was used in place of Compound 1-c in Step 4 of Example 1 to obtain Compound 1 Compound 12 was prepared (4.1 g, 32% yield, MS: [M + H] < ⁺ > = 474).

Example  13: Preparation of compound 13

Compound 13 was prepared in the same manner as in the production of Compound 11, except that Intermediate E was used instead of Intermediate D in Example 11, and phenanthrene-9-ylboronic acid was used instead of naphthalene-2-ylboronic acid 4.3 g, MS: [M + H] < ⁺ > = 525).

Example  14: Preparation of compound 14

Compound 14 was prepared in the same manner as in the production of Compound 11, except for using Intermediate E instead of Intermediate D and using naphthalene-1-ylboronic acid instead of naphthalene-2-ylboronic acid (Example 4.5 g, MS: [M + H] < ⁺ > = 475).

Example  15: Preparation of compound 15

Compound 15 was prepared (5.3 g, MS: [M + H] ⁺ = 494) in the same manner as in the preparation of Compound 11, except that Intermediate F was used instead of Intermediate D in Example 11.

[ Experimental Example ]

Experimental Example  One

A glass substrate coated with ITO (Indium Tin Oxide) with a thickness of 1,400 Å was immersed in distilled water dissolved in detergent and washed with ultrasonic waves. As a detergent, Decon (TM) CON705 product of Fischer Co. was used, and distilled water which was secondly filtered with a 0.22 μm sterilizing filter manufactured by 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 for 10 minutes, dried, and then transported to a plasma cleaner. The substrate was cleaned using oxygen plasma for 5 minutes, and then the substrate was transported by a vacuum evaporator.

The following HI-A compound and the following HAT-CN compound were sequentially deposited by thermal vacuum deposition to a thickness of 650 ANGSTROM and a thickness of 50 ANGSTROM, respectively, on the thus prepared ITO transparent electrode to form a hole injection layer. The HT-A compound shown below was vacuum deposited on the hole injection layer to a thickness of 600 Å to form a hole transport layer. The HT-B compound was thermally vacuum deposited on the hole transport layer to a thickness of 50 Å to form an electron blocking layer. The compound 1 prepared above and the following BD compound were vacuum deposited on the electron blocking layer at a weight ratio of 96: 4 to a thickness of 200 ANGSTROM to form a light emitting layer. The following ET-A compound was vacuum deposited on the light emitting layer to a thickness of 50 Å to form a hole blocking layer. On the hole blocking layer, the following ET-B compound and the following Liq compound were thermally vacuum deposited to a thickness of 310 Å at a weight ratio of 1: 1 to form an electron transport layer. The following Liq compound was vacuum deposited on the electron transport layer to a thickness of 5 Å to form an electron injection layer. Magnesium and silver were sequentially deposited on the electron injecting layer at a weight ratio of 10: 1 to a thickness of 120 Å and aluminum to a thickness of 1000 to form a cathode, thereby preparing an organic light emitting device.

Experimental Example  2 to 15

An organic light emitting device was prepared in the same manner as in Experimental Example 1, except that the compound described in the following Table 1 was used instead of the compound 1 in Experimental Example 1.

Comparative Experimental Example  1 to 8

An organic light emitting device was prepared in the same manner as in Experimental Example 1, except that the compound described in the following Table 1 was used instead of the compound 1 in Experimental Example 1. In Table 1, the compounds of BH-A, BH-B, BH-C, BH-D, BH-E, BH-F, BH-G and BH-H are respectively as follows.

The voltage, efficiency, and lifetime (T95) were measured by applying current to the organic light emitting device manufactured in the Experimental Example and the Comparative Experimental Example, and the results are shown in Table 1 below. At this time, the voltage and efficiency were measured by applying a current density of 10 mA / cm ² , and T95 means the time until the initial luminance decreased to 95% at a current density of 20 mA / cm ² .

Host
matter Voltage (V)
(@ 10 mA / cm ² ) Efficiency (cd / A)
(@ 10 mA / cm ² ) Life (T95, hr)
(@ 20 mA / cm ² ) Experimental Example 1 Compound 1 3.32 6.07 65 Experimental Example 2 Compound 2 3.31 6.03 60 Experimental Example 3 Compound 3 3.33 6.08 66 Experimental Example 4 Compound 4 3.34 6.11 68 Experimental Example 5 Compound 5 3.44 6.07 67 Experimental Example 6 Compound 6 3.45 6.09 65 Experimental Example 7 Compound 7 3.48 6.10 63 Experimental Example 8 Compound 8 3.44 6.06 61 Experimental Example 9 Compound 9 3.35 5.71 55 Experimental Example 10 Compound 10 3.34 5.66 53 Experimental Example 11 Compound 11 3.30 5.88 59 Experimental Example 12 Compound 12 3.39 5.80 58 Experimental Example 13 Compound 13 3.38 5.55 51 Experimental Example 14 Compound 14 3.36 5.56 50 Experimental Example 15 Compound 15 3.33 6.02 60 Comparative Experimental Example 1 BH-A 4.25 5.13 40 Comparative Experimental Example 2 BH-B 3.81 5.10 20 Comparative Experimental Example 3 BH-C 3.71 5.21 20 Comparative Experimental Example 4 BH-D 4.81 3.12 10 Comparative Experiment Example 5 BH-E 4.80 3.51 13 Comparative Experimental Example 6 BH-F 5.28 2.12 5 Comparative Example 7 BH-G 3.31 5.10 40 Comparative Experiment Example 8 BH-H 3.35 5.06 41

Compared with the BH-A structure of Comparative Experimental Example 1, when the dibenzofuran or dibenzothiophene is directly bonded to the anthracene, the HOMO energy level is higher than that of the anthracene, and the hole voltage is lowered . As can be seen from Comparative Experimental Example 2 and Comparative Experimental Example 3, even when dibenzofuran or dibenzothiophene bonds directly to anthracene like BH-B or BH-C, when only the phenyl group is present on the opposite side, It was too small to lower the thermal stability, resulting in a decrease in the efficiency and the life span. In Comparative Experimental Example 4, Comparative Experiment Example 5 and Comparative Experiment Example 6 in which BH-D, BH-E, and BH-F in which molecular weight was increased by introducing a substituent into dibenzofuran to secure thermal stability, Lowering of the efficiency, and lowering of the life span. From the above results, it can be seen that dibenzofurane or dibenzothiophene bonds directly to anthracene and an aryl group having 10 to 20 carbon atoms on the opposite side as in the structure of formula (1) have.

In addition, deuterium has a higher atomic mass than hydrogen and has a small vibration mode which increases the nonradiative decay time in the excited state, in particular, the stability of the triplet exciton. The increased stability of the triplet exciton ultimately amplifies the TTF phenomenon and can contribute to the improvement of the efficiency and lifetime of blue fluorescence. The results of Experiments 1 to 15 shown in Table 1 show such an effect in comparison with Comparative Experiment 7 and Comparative Experiment 8 in which deuterium is not substituted. From the results of Experimental Examples, it can be seen that the more deuterium is contained in dibenzofuran or dibenzothiophen, the closer the deuterium is located to the anthracene in which the triplet exciton is located, the greater the effect becomes.

As a result, when a material having the structure of Chemical Formula (1) is used as a blue light emitting layer host of an organic electroluminescent device, a device of low voltage, high efficiency and long life can be obtained.

1: substrate 2: anode
3: light emitting layer 4: cathode
5: Hole injection layer 6: Hole transport layer
7: light emitting layer 8: electron transporting layer

Claims (9)

A compound represented by the following formula (1):
[Chemical Formula 1]

In Formula 1,
X is O, or S,
R ₁ to R ₈ are each independently hydrogen or deuterium, at least one of R ₁ to R ₈ is deuterium, and any one of R ₁ to R ₄ is represented by the following formula (2)
(2)

Ar ₁ is substituted or unsubstituted C _10-20 aryl.
The method according to claim 1,
(1) is a compound represented by the following general formula (1-1), (1-2), (1-3)
compound:
[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

In the above Formulas 1-1 to 1-4,
X and Ar &_lt; 1 > are as defined in claim ₁ ,
In Formula 1-1, R ₁ and R ₃ to R ₈ are each independently hydrogen or deuterium, and at least one of R ₁ and R ₃ to R ₈ is deuterium,
In Formula 1-2, R ₂ to R ₈ are each independently hydrogen or deuterium, at least one of R ₂ to R ₈ is deuterium,
Wherein R ₁ , R ₂ and R ₄ to R ₈ are each independently hydrogen or deuterium, at least one of R ₁ , R ₂ and R ₄ to R ₈ is deuterium,
In Formula 1-4, R ₁ to R ₃ and R ₅ to R ₈ are each independently hydrogen or deuterium, and at least one of R ₁ to R ₃ and R ₅ to R ₈ is deuterium.
3. The method of claim 2,
Among R ₁ and R ₃ to R ₈ in Formula 1-1, R ₁ ; R ₃ ; R ₄ ; R ₅ ; R ₆ ; R ₇ ; R ₈ ; R ₁ and R ₃ ; R ₆ and R ₈ ; R ₁ , R ₃ and R ₄ ; R ₅ to R ₈ ; Or R ₁ and R ₃ to R ₈ are deuterium and the remainder is hydrogen,
compound.
3. The method of claim 2,
Among R ₂ to R ₈ in the above formula (1-2), R ₂ ; R ₃ ; R ₄ ; R ₅ ; R ₆ ; R ₇ ; R ₈ ; R ₂ and R ₄ ; R ₆ and R ₈ ; R ₂ to R ₄ ; R ₅ to R ₈ ; Or R < ₂ > to R < ₈ >
compound.
3. The method of claim 2,
Among R ₁ , R ₂ and R ₄ to R ₈ of the above formula 1-3, R ₁ ; R ₂ ; R ₄ ; R ₅ ; R ₆ ; R ₇ ; R ₈ ; R ₂ and R ₄ ; R ₆ and R ₈ ; R ₁ , R ₂ and R ₄ ; R ₅ to R ₈ ; Or R ₁ , R ₂ and R ₄ to R ₈ are deuterium and the remainder is hydrogen,
compound.
3. The method of claim 2,
Among R ₁ to R ₃ and R ₅ to R ₈ in the general formula 1-4, R ₁ ; R ₂ ; R ₃ ; R ₅ ; R ₆ ; R ₇ ; R ₈ ; R ₁ and R ₃ ; R ₆ and R ₈ ; R ₁ to R ₃ ; R ₅ to R ₈ ; Or R <_1> to R <_3> and R <_5> to R <_8>
compound.
The method according to claim 1,
Ar ₁ is naphthyl, phenylnaphthyl, phenanthrenyl, or triphenylenyl,
compound.
The method according to claim 1,
Wherein said compound is selected from the group consisting of &lt; RTI ID = 0.0 &gt;
compound:

A first electrode; A second electrode facing the first electrode; And at least one organic material layer provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer comprises the compound of any one of claims 1 to 8 &Lt; / RTI &gt;

Images