KR20180045798A - Novel hetero-cyclic compound and organic light emitting device comprising the same - Google Patents

Abstract

The present invention provides a novel compound and an organic light emitting device using the same. A compound represented by the chemical formula 1 can be used as a material of an organic material layer of the organic light emitting device, and can improve the efficiency, the driving voltage and/or the lifetime characteristics of the organic light emitting device.

Description

TECHNICAL FIELD [0001] The present invention relates to novel compounds and organic light emitting devices using the same,

Cross-reference with related application (s)

This application claims the benefit of priority based on Korean Patent Application No. 10-2016-0139260, filed October 25, 2016, the entire contents of which are incorporated herein by reference.

The present invention relates to a novel compound and an organic light emitting device comprising 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. In order to increase the efficiency and stability of the organic light emitting device, the organic material layer may have a multilayer structure composed of different materials. 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 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.

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 novel compound and an organic light emitting device comprising the same.

The present invention provides a compound represented by the following formula (1): < EMI ID =

[Chemical Formula 1]

In Formula 1,

X < ₁ > is O or S,

Y ₁ to Y ₃ are each independently N or CR ₃ , at least one of Y ₁ to Y ₃ is N,

L ₁ and L ₂ are each independently a bond; Substituted or unsubstituted C _6-60 arylene; Or substituted or unsubstituted C _2-60 heteroarylene containing at least one heteroatom selected from the group consisting of O, N, Si and S,

Ar ₁ and Ar ₂ are each independently a substituted or unsubstituted C _6-60 aryl; Or substituted or unsubstituted C _2-60 heteroaryl containing 1 to 3 heteroatoms selected from the group consisting of N, O and S,

Ar ₃ is N (Ar ₁₁ ) (Ar ₁₂ ); Or substituted or unsubstituted C _2-60 heteroaryl containing 1 to 3 hetero atoms selected from the group consisting of N, O and S, the atom bonding to L ₂ is a hetero atom,

Wherein Ar ₁₁ and Ar ₁₂ are each independently a substituted or unsubstituted C _6-60 aryl; Or substituted or unsubstituted C _2-60 heteroaryl containing 1 to 3 heteroatoms selected from the group consisting of N, O and S,

R ₁ to R ₃ are each independently hydrogen; heavy hydrogen; halogen; Cyano; Amino; Substituted or unsubstituted C _1-6 alkyl; C _1-60 haloalkyl; Substituted or unsubstituted C _1-60 alkoxy; Substituted or unsubstituted C _1-60 haloalkoxy; Substituted or unsubstituted C _3-60 cycloalkyl; Substituted or unsubstituted C _2-60 alkenyl; Substituted or unsubstituted C _6-60 aryl; Substituted or unsubstituted C _6-60 aryloxy; Or a substituted or unsubstituted C _2-60 heterocyclic group containing at least one heteroatom selected from the group consisting of N, O and S,

a1 and a2 are each independently an integer of 0 to 3;

The present invention also provides 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 .

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. In particular, the compound represented by Formula 1 can be used as a hole injecting, hole transporting, hole injecting and transporting, light emitting, 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 치환기에 연결되는 결합을 의미하고, 단일 결합은 L로 표시되는 부분에 별도의 원자가 존재하지 않은 경우를 의미한다. In the present specification,

Means a bond connected to another substituent, and a single bond means a case where no separate atom exists in a portion represented by L. [

As used herein, the term " substituted or unsubstituted " A halogen group; Cyano; A nitro group; A hydroxy group; A carbonyl group; An ester group; Imide; An amino group; Phosphine oxide groups; An alkoxy group; An aryloxy group; An alkyloxy group; Arylthioxy group; An alkylsulfoxy group; Arylsulfoxy group; Silyl group; Boron group; An alkyl group; Cycloalkyl groups; An alkenyl group; An aryl group; Aralkyl groups; An aralkenyl group; An alkylaryl group; An alkylamine group; An aralkylamine group; A heteroarylamine group; An arylamine group; Arylphosphine groups; Or a heterocyclic group containing at least one of N, O and S atoms, or a substituted or unsubstituted group in which at least two of the above-exemplified substituents are connected to each other . 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.

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

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

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

In the present specification, the silyl group specifically includes a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, But are not limited thereto.

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

In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 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 isopropyl group, a n-butyl group, an isobutyl group, a tert-butyl group, But are not limited to, pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, , n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, But are not limited to, dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl and 5-methylhexyl.

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 30 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- 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 phenanthryl group, a pyrenyl group, a perylenyl group, a klycenyl group and a fluorenyl group.

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.

In the present specification, the heterocyclic group is a hetero ring group containing at least one of O, N, Si and S as a hetero atom, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60 carbon atoms. Examples of the heterocyclic group include a thiophene group, a furan group, a pyrrolyl group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a triazole group, a pyridyl group, a bipyridyl group, a pyrimidyl group, , A pyridazinyl group, a pyrazinyl group, a quinolinyl group, a quinazolinyl group, a quinoxalinyl group, a phthalazinyl group, a pyridopyrimidinyl group, a pyridopyranyl group, a pyrazinopyranyl group, an isoquinoline group, , A carbazole group, a benzoxazole group, a benzoimidazole group, a benzothiazole group, a benzocarbazole group, a benzothiophene group, a dibenzothiophene group, a benzofuranyl group, a phenanthroline, an isoxazolyl group, A benzyl group, a benzyl group, a benzyl group, a benzyl group, a benzyl group, a benzyl group, a benzyl group, a benzyl group, a benzyl group,

In the present specification, the aryl group in the aralkyl group, the aralkenyl group, the alkylaryl group and the arylamine group is the same as the aforementioned aryl group. In the present specification, the alkyl group in the aralkyl group, the alkylaryl group, and the alkylamine group is the same as the alkyl group described above. In the present specification, the heteroaryl among the heteroarylamines can be applied to the aforementioned heterocyclic group. In the present specification, the alkenyl group in the aralkenyl group is the same as the above-mentioned alkenyl group. In the present specification, the description of the aryl group described above can be applied except that arylene is a divalent group. In the present specification, the description of the above-mentioned heterocyclic group can be applied except that the heteroarylene is a divalent group. In the present specification, the description of the above-mentioned aryl group or cycloalkyl group can be applied except that the hydrocarbon ring is not a monovalent group and two substituents are bonded to each other. In the present specification, the description of the above-mentioned heterocyclic group can be applied except that the heterocyclic ring is not a monovalent group and two substituents are bonded to each other.

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

In Formula 1,

Y ₁ and Y ₂ are N, Y ₃ is CR ₃ ,

Y ₁ and Y ₃ are N, Y ₂ is CR ₃ , or

Y ₁ , Y _2, and Y ₃ may be N.

E.g,

Y ₁ and Y ₂ are N, Y ₃ is CH,

Y ₁ and Y ₃ are N, Y ₂ is CH, or

Y ₁ , Y _2, and Y ₃ may be N.

Further, L ₁ and L ₂ each independently may be bonded, substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, or substituted or unsubstituted naphthylene.

For example, L ₁ and L ₂ may each independently be a bond,

.

.

Specifically, for example, L ₁ and L ₂ may each independently be a bond,

.

.

Ar ₁ and Ar ₂ each independently may be any one selected from the group consisting of:

In the above,

Z ₁ and Z ₂ are each independently hydrogen; heavy hydrogen; halogen; Cyano; Amino; C _1-20 alkyl; C _1-20 haloalkyl; Or C _6-20 aryl,

c1 and c2 are each independently an integer of 0 to 3;

Wherein Z ₁ and Z ₂ are each independently hydrogen or phenyl and c 1 and c 2 are each independently 0 or 1.

For example, Ar ₁ and Ar ₂ may each independently be selected from the group consisting of:

Ar ₃ represents N (Ar ₁₁ ) (Ar ₁₂ ); Or substituted or unsubstituted C _2-60 heteroaryl containing 1 to 3 hetero atoms selected from the group consisting of N, O and S, wherein the atom bonded to L ₂ is a heteroatom, more specifically, Lt; / RTI >

More specifically, Ar < ₃ > may be any one selected from the group consisting of:

In the above,

X ₂ and X ₃ are each independently O, S, NZ ₁₃ , or CZ ₁₄ Z ₁₅ ,

Ar ₁₁ and Ar ₁₂ each independently represent a substituted or unsubstituted C _6-20 aryl; Or substituted or unsubstituted C _2-20 heteroaryl containing 1 to 3 hetero atoms selected from the group consisting of N, O and S,

Z ₁₁ to Z ₁₅ each independently represent hydrogen; heavy hydrogen; halogen; Cyano; Amino; C _1- 20 alkyl; C _1-20 haloalkyl; Or C _6-20 aryl,

n1 and n2 are each independently an integer of 0 to 3;

Wherein Ar ₁₁ and Ar ₁₂ are phenyl and Z ₁₁ to Z ₁₅ are each independently hydrogen, methyl, or phenyl, and n 1 and n 2 each independently may be 0 or 1.

For example, Ar < ₃ > may be any one selected from the group consisting of:

Each of R ₁ to R ₃ independently represents hydrogen; heavy hydrogen; halogen; Cyano; Amino; methyl; Or phenyl, and a1 and a2 may each independently be 0 or 1.

For example, R ₁ to R ₃ may be hydrogen.

Here, a1 represents the number of R ₁ , and when a ₁ is 2 or more, two or more R _{1 s} may be the same or different from each other. a2, c1, c2, n1 and n2 can be understood with reference to the description of a1 and the structure of the above formula.

In addition, the compound may be any one selected from the group consisting of the following compounds:

The compound represented by Formula 1 has a structure in which a 6-membered heterocyclic group containing at least one N atom and a Ar ₃ substituent group as described above are linked to a specific position of dibenzofuran or dibenzothiophene core, The organic light emitting device using the organic EL device may have high efficiency, low driving voltage, high brightness and long life.

The compound represented by the formula (1) can be prepared, for example, by the following reaction scheme. The above production method can be more specific in the production example to be described later.

[Reaction Scheme 1]

In the above Reaction Scheme 1,

A and E are each independently a halogen group such as chloro, bromo and the like,

D is a boron (B) -based organic group such as a boronic acid group, a boronic acid ester group, or a boronic acid pinacol ester group,

X ₁ , Y ₁ to Y ₃ , L ₁ , L ₂ , R ₁ , R ₂ , a ₁ , and a ₂ are as defined above.

Specifically, the compound (I) of the formula (1) is prepared by Suzuki coupling reaction of the organoboron compound (II) with the halide (III) in the presence of a base and a palladium catalyst to prepare a compound of the formula (IV) Step S1; And reacting the compound of formula (IV) with a compound of formula (V) (S2).

In the step (S1) for preparing the compound of the formula (IV), sodium carbonate, potassium carbonate, sodium hydroxide or potassium hydroxide can be used as the base, and as the palladium-based catalyst, tetrakis- phosphine) palladium _{(Pd (PPH 3) 4)} , palladium acetate and the like can be used. The reaction can also be carried out in an organic solvent such as tetrahydrofuran (THF), N, N-dimethylformamide (DMF), dimethylsulfoxide (DMSO) or toluene.

The Suzuki coupling reaction may be carried out at a temperature in the range of 80 ° C to 120 ° C.

In the step (S2) for the preparation of the compound of the formula (I), [M (Pt-Bu) 3, such as Pd (Pt-Bu ₃ ) _{2 3} ) ₂ ] (M = Pd, Pt) in a non-polar solvent such as xylene. In addition, More specifically, a non-nucleophilic base such as NaOt-Bu (sodium tert-butoxide) may be further added.

Preparation of the organometallic compound (I) represented by the above formula (1) to be prepared by appropriately substituting the starting compound, the compound (II), the compound (III) and the compound (V) Is possible.

Meanwhile, the present invention provides an organic light emitting device comprising 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 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 .

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.

The organic material layer may include a hole injecting layer, a hole transporting layer, or a layer simultaneously injecting and transporting holes. 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 electron transport layer, the electron injection layer, or the layer which simultaneously transports electrons and electrons may include a layer that simultaneously performs the electron transport layer, the electron injection layer, or the electron transport and electron injection. ≪ / RTI >

The organic material layer may include a light emitting layer and an electron transporting layer, and the electron transporting layer may include a compound represented by the general formula (1).

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, in the organic light emitting device of the present invention, in addition to the light emitting layer as the organic material layer, a hole injecting layer and a hole transporting layer between the first electrode and the light emitting layer, and an electron transporting layer and an electron injecting layer between the light emitting layer and the second electrode are further included . ≪ / RTI > However, the structure of the organic light emitting device is not limited thereto, and may include fewer or more organic layers.

The organic light emitting device according to the present invention may be a normal type organic light emitting device in which an anode, at least one organic layer, 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 an anode, one or more organic compound layers 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 may be manufactured by materials and methods known in the art, except that at least one of the organic layers includes the compound represented by 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 material 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 on the organic material layer, 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.

The compound represented by Formula 1 may be formed into an organic layer by a solution coating method as well as a vacuum evaporation 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 from a cathode material on a substrate (WO 2003/012890). However, the manufacturing method is not limited thereto.

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

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 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 preferable 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. The hole transport material is a material capable of transporting holes from the anode or the hole injection layer to the light emitting layer. The 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 as described above. The host material may further include a condensed aromatic ring derivative or a hetero ring-containing compound in addition to the compound represented by the formula (1). 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.

More specifically, they may be mixed with the following compound (H2) at a mixing ratio of 10:90 to 90:10, more specifically 40:60 to 60:40.

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 including the compound represented by Formula 1 will be described in detail below. 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: Intermediates A1 and A2  Compound synthesis

(1) Preparation of intermediate A1

2-iodobenzene-1,3-diol (100 g, 0.42 mol) and 3-chloro-2-fluorophenyl boronic acid (81.3 g, 0.47 mol) were dissolved in 1000 mL of tetrahydrofuran in a 2000 mL round- (175 g, 1.27 mol) dissolved in 500 ml of water was added. Bis (tri- tert- butylphosphine) palladium (0) (2.17 g, 4.23 mmol) was added thereto and the mixture was heated with stirring for 1 hour. (80.2 g, yield: 79%, MS: [M + H] < + >, M < + > H). The reaction mixture was concentrated under reduced pressure and the residue was recrystallized using hexane to obtain Intermediate A1 ] ⁺ = 239).

(2) Preparation of intermediate A2

Intermediate A1 (80.2 g, 0.33 mol) and potassium carbonate (139 g, 1.01 mol) were dissolved in 400 mL of N-methyl-2-pyrrolidone and the mixture was heated with stirring for 1 hour. The temperature is lowered to room temperature and the solution is reprecipitated in water. (53.2 g, yield 72%, MS: [M + H] < ⁺ >) was obtained by completely dissolving in dichloromethane, washing with water, drying with anhydrous magnesium sulfate, concentration under reduced pressure, recrystallization using ethanol, 219).

Manufacturing example  2: Intermediate A3 and A4  Compound synthesis

(1) Preparation of intermediate A3

(47.2 g, 0.34 mol) was dissolved in 100 mL of water, and then nonafluorobutanesulfonyl fluoride (45.2 mL, 0.25 mol) was added to the solution at 0 ° C for 25 minutes Let it fall slowly. Thereafter, the mixture was stirred at room temperature for 3 hours. After completion of the reaction, the reaction mixture was filtered and completely dissolved in dichloromethane, washed with water, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, recrystallized using ethanol, and dried to obtain Intermediate A3 (83.3 g, yield: 73% M + H] < ⁺ > = 501).

(2) Preparation of intermediate A4

Intermediate A3 (83.3 g, 0.17 mol), 4,4,5,5-tetramethyl- [1,3,2] dioxaborane (46.5 g, 0.18 mol), Pd (dppf) Cl ₂ (1.22 g, 1.66 mmol) , KOAc (49.0 g, 0.50 mol) were placed in dioxane (900 mL) and stirred at reflux for 10 hours. The temperature was lowered to room temperature and the solvent was concentrated under reduced pressure. The concentrate was completely dissolved in CHCl ₃ and washed with water. The solution in which the product was dissolved was concentrated under reduced pressure and purified by column chromatography. Intermediate A4 was obtained (95.2 g, yield 86%, MS: [M + H] < ⁺ > = 329).

Manufacturing example  3: Intermediate A5  Compound synthesis

Intermediate A4 (30.0 g, 0.09 mol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (24.4 g, 0.091 mmol) (Triphenylphosphine) palladium (1.05 g, 0.91 mmol) was added to potassium carbonate (37.9 g, 0.27 mol) dissolved in 120 ml of water, and the mixture was heated with stirring for 9 hours Respectively. (32.1 g, yield 81%, MS: [M + H 2] < + >), ] ⁺ = 433).

Manufacturing example  4: Intermediate A6  Compound synthesis

Except that 2-chloro-4- (dibenzo [b, d] furan-4-yl) -6-phenyl-1,3,5-triazine was used in place of 2-chloro-4,6- Intermediate A6 was prepared in the same manner as in the preparation of A5.

Manufacturing example  5: Intermediate A7  Compound synthesis

Except that 2-chloro-4- (dibenzo [b, d] furan-1-yl) -6-phenyl-1,3,5-triazine was used in place of 2-chloro-4,6- Intermediate A7 was prepared in the same manner as in the preparation of A5.

Manufacturing example  6: Intermediate A8  Compound synthesis

Except that 2-chloro-4- (dibenzo [b, d] furan-2-yl) -6-phenyl-1,3,5-triazine was used in place of 2-chloro-4,6- Intermediate A8 was prepared in the same manner as in the preparation of A5.

Manufacturing example  7: Intermediate A9  Compound synthesis

Except that 2-chloro-4- (dibenzo [b, d] furan-3-yl) -6-phenyl-1,3,5-triazine was used in place of 2-chloro-4,6- Intermediate A9 was prepared in the same manner as in the preparation of A5.

Manufacturing example  8: Intermediate A10  Compound synthesis

Except that 2-chloro-4- (dibenzo [b, d] thiophen-4-yl) -6-phenyl-1,3,5-triazine was used in place of 2-chloro-4,6- Intermediate A10 was prepared in the same manner as in the preparation of A5.

Manufacturing example  9: Intermediate A11  Compound synthesis

Except that 2-chloro-4- (dibenzo [b, d] thiophen-3-yl) -6-phenyl-1,3,5-triazine was used in place of 2-chloro-4,6- Intermediate A11 was prepared in the same manner as in the preparation of A5.

Manufacturing example  10: Intermediate A12  Compound synthesis

Except that 2- (4-bromophenyl) -4,6-diphenyl-1,3,5-triazine was used in place of 2-chloro-4,6-diphenyltriazine, intermediate A12.

Manufacturing example  11: Intermediate A13  Compound synthesis

Except that 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine was used in place of 2-chloro-4,6-diphenyltriazine, intermediate A13.

Manufacturing example  12: Intermediate A14  Compound synthesis

Intermediate A14 was prepared in the same manner as Intermediate A5 except that 2-chloro-4,6-diphenylpyrimidine was used instead of 2-chloro-4,6-diphenyltriazine.

Manufacturing example  13: Intermediate A15  Compound synthesis

Intermediate A15 was prepared in the same manner as Intermediate A5 except for using 4-chloro-2,6-diphenylpyrimidine instead of 2-chloro-4,6-diphenyltriazine.

[Example]

Example  1: Compound 1 of  synthesis

(10.0 g, 0.023 mol), diphenylamine (3.90 g, 0.19 mol), bis (tri-tert-butylphosphine) palladium (0) (0.12 g, 0.23 mmol) and sodium tert-butoxide (3.32 g, 0.035 mol) were placed in 110 ml of xylene and the mixture was stirred with heating for 9 hours. After lowering the temperature to room temperature and removing the salt by filtration, the xylene is concentrated under reduced pressure, and the residue is dissolved with dichlorobenzene, washed with water, and then the water is removed with MgSO 4 and the solvent is removed. Then, the compound 1 was prepared by recrystallization using N-methyl-2-pyrrolidone. (9.2 g, 70% yield, MS: [M + H] < ⁺ > = 567)

Example  2: Compound 2 of  synthesis

Compound 2 was prepared in the same manner as Compound 1 except di ([1,1'-biphenyl] -4-yl) amine was used instead of diphenylamine. (Yield: 74%, MS: [M + H] < ⁺ > = 719)

Example  3: Compound 3 of  synthesis

Except that N - ([1,1'-biphenyl] -4-yl) -9,9-dimethyl-9H-fluoren-2-amine was used in place of diphenylamine 3. (Yield: 72%, MS: [M + H] < ⁺ > = 759)

Example  4: Compound 4 of  synthesis

Compound 4 was prepared in the same manner as Compound 1 except that 9H-carbazole was used instead of diphenylamine. (Yield: 72%, MS: [M + H] < ⁺ > = 565)

Example  5: Compound 5 of  synthesis

Compound 5 was prepared in the same manner as Compound 1 except that 7H-benzo [c] carbazole was used instead of diphenylamine. (Yield: 77%, MS: [M + H] < ⁺ > = 615)

Example  6: Compound 6 of  synthesis

Compound 6 was prepared in the same manner as Compound 1 except for using 7,7-dimethyl-5,7-dihydroindeno [2,1-b] carbazole instead of diphenylamine. (Yield: 80%, MS: [M + H] < ⁺ > = 681)

Example  7: Compound 7's  synthesis

Compound 7 was prepared in the same manner as Compound 1 except for using 12,12-dimethyl-11,12-dihydroindeno [2,1-a] carbazole instead of diphenylamine. (Yield: 82%, MS: [M + H] < ⁺ > = 681)

Example  8: Compound 8 of  synthesis

Compound 8 was prepared in the same manner as Compound 1 except for using 11-phenyl-11,12-dihydroindolo [2,3-a] carbazole instead of diphenylamine. (Yield: 82%, MS: [M + H] < ⁺ > = 730)

Example  9: Compound 9 of  synthesis

Compound 9 was prepared in the same manner as Compound 1 except that 5-phenyl-5,12-dihydroindolo [3,2-a] carbazole was used instead of diphenylamine. (Yield: 79%, MS: [M + H] < ⁺ > = 730)

Example  10: Compound Ten  synthesis

Compound 10 was prepared in the same manner as Compound 1 except that Intermediate A6 was used instead of Intermediate A5. (Yield: 74%, MS: [M + H] < ⁺ > = 657)

Example  11: Compound Eleven  synthesis

Compound 11 was prepared in the same manner as Compound 1 except that Intermediate A5 and Intermediate A6 and N-phenyl- [1,1'-biphenyl] -4 -amine were used instead of diphenylamine. (Yield: 75%, MS: [M + H] < ⁺ > = 733)

Example  12: Compound 12 of  synthesis

Compound 12 was prepared in the same manner as Compound 1 except that Intermediate A5 and Intermediate A6 and 9H-carbazole were used instead of diphenylamine. (Yield 77%, MS: [M + H] < ⁺ > = 655)

Example  13: Compound Thirteen  synthesis

Compound 13 was prepared in the same manner as Compound 1 except that Intermediate A5 and Intermediate A6 and 11H-benzo [a] carbazole were used instead of diphenylamine. (Yield: 82%, MS: [M + H] < ⁺ > = 705)

Example  14: Compound 14 of  synthesis

Compound 14 was prepared in the same manner as Compound 1 except that Intermediate A5 and Intermediate A6 and 7,7-dimethyl-5,7-dihydroindeno [2,1-b] carbazole were used instead of diphenylamine. (Yield 84%, MS: [M + H] < ⁺ > = 771)

Example  15: Compound Fifteen  synthesis

Compound 15 was prepared in the same manner as Compound 1 except that Intermediate A5 and Intermediate A6 and 12-phenyl-5,12-dihydroindolo [3,2-a] carbazole were used instead of diphenylamine. (Yield: 84%, MS: [M + H] < ⁺ > = 820)

Example  16: Compound 16  synthesis

Compound 16 was prepared in the same manner as Compound 1 except that Intermediate A7 was used instead of Intermediate A5. (Yield: 71%, MS: [M + H] < ⁺ > = 657)

Example  17: Compound 17  synthesis

Except that Intermediate A5 and Intermediate A7 were used instead of diphenylamine and N - ([1,1'-biphenyl] -4-yl) - [1,1'-biphenyl] , Compound 17 was prepared. (Yield: 74%, MS: [M + H] < ⁺ > = 809)

Example  18: Compound 18  synthesis

Compound 18 was prepared in the same manner as Compound 1 except for Intermediate A5 and 9H-carbazole, instead of Intermediate A7 and diphenylamine. (Yield 77%, MS: [M + H] < ⁺ > = 657)

Example  19: Compound 19's  synthesis

Compound 19 was prepared in the same manner as in the preparation of Compound 1 except for Intermediate A5 and Intermediate A7 and 7H-benzo [c] carbazole instead of diphenylamine. (Yield: 79%, MS: [M + H] < ⁺ > = 705)

Example  20: Compound Twenty  synthesis

Compound 20 was prepared in the same manner as Compound 1 except for the intermediate A5 and the intermediate A7 and 7,7-dimethyl-5,7-dihydroindeno [2,1-b] carbazole instead of diphenylamine. (Yield: 83%, MS: [M + H] < ⁺ > = 771)

Example  21: Compound 21  synthesis

Compound 21 was prepared in the same manner as Compound 1 except that Intermediate A5 and Intermediate A7 and 5-phenyl-5,12-dihydroindolo [3,2-a] carbazole were used instead of diphenylamine. (Yield: 83%, MS: [M + H] < ⁺ > = 820)

Example  22: Compound 22 of  synthesis

Compound 22 was prepared in the same manner as Compound 1 except for the intermediate A5 and the intermediate A8 and di ([1,1'-biphenyl] -4-yl) amine instead of diphenylamine. (Yield: 73%, MS: [M + H] < ⁺ > = 809)

Example  23: Compound 23 of  synthesis

Compound 23 was prepared in the same manner as Compound 1 except for Intermediate A5 and Intermediate A8 and 9H-carbazole instead of diphenylamine. (Yield: 72%, MS: [M + H] < ⁺ > = 655)

Example  24: Synthesis of Compound 24

Compound 24 was prepared in the same manner as Compound 1 except for Intermediate A5 and Intermediate A8 and 5H-benzo [b] carbazole instead of diphenylamine. (Yield: 79%, MS: [M + H] < ⁺ > = 705)

Example  25: Synthesis of Compound 25

Compound 25 was prepared in the same manner as in the preparation of Compound 1 except for Intermediate A5 and Intermediate A8 and 7,7-dimethyl-7,12-dihydroindeno [1,2-a] carbazole instead of diphenylamine. (Yield: 79%, MS: [M + H] < ⁺ > = 771)

Example  26: Synthesis of Compound 26

Compound 26 was prepared in the same manner as Compound 1 except that Intermediate A5 and Intermediate A8 and 12-phenyl-5,12-dihydroindolo [3,2-a] carbazole were used instead of diphenylamine. (Yield: 85%, MS: [M + H] < ⁺ > = 820)

Example  27: Compound 27  synthesis

Compound 27 was prepared in the same manner as Compound 1 except that Intermediate A5 and 13,13-dimethyl-11,13-dihydrochromeno [3,2-b] carbazole were used instead of Intermediate A8 and diphenylamine. (Yield: 80%, MS: [M + H] < ⁺ > = 787)

Example  28: Compound 28 of  synthesis

Except that the intermediate A5 and the intermediate A9 instead of diphenylamine and the compound 1 except for N - ([1,1'-biphenyl] -4-yl) -9,9-dimethyl-9H-fluoren- Compound 28 was prepared in the same manner. (Yield: 77%, MS: [M + H] < ⁺ > = 849)

Example  29: Compound 29 of  synthesis

Compound 29 was prepared in the same manner as Compound 1 except for the intermediate A9 and 12,12-dimethyl-5,12-dihydroindeno [1,2-c] carbazole instead of the intermediate A9 and diphenylamine. (Yield: 79%, MS: [M + H] < ⁺ > = 771)

Example  30: Compound Thirty  synthesis

Compound 30 was prepared in the same manner as Compound 1 except that Intermediate A5 and Intermediate A9 and 12-phenyl-5,12-dihydroindolo [3,2-a] carbazole were used instead of diphenylamine. (Yield: 80%, MS: [M + H] < ⁺ > = 820)

Example  31: Compound 31 of  synthesis

Compound 31 was prepared in the same manner as Compound 1 except for the intermediate A9 and 13,13-dimethyl-7,13-dihydrochromeno [2,3-b] carbazole instead of the intermediate A9 and diphenylamine. (Yield: 82%, MS: [M + H] < ⁺ > = 787)

Example  32: Compound 32  synthesis

Compound 32 was prepared in the same manner as Compound 1 except for the intermediate A10 and di ((1,1'-biphenyl) -4-yl) amine instead of the intermediate A10 and diphenylamine. (Yield: 73%, MS: [M + H] < ⁺ > = 825)

Example  33: Compound 33 of  synthesis

Compound 33 was prepared in the same manner as in the preparation of Compound 1 except for Intermediate A5 and Intermediate A10 and 5H-benzo [b] carbazole instead of diphenylamine. (Yield: 77%, MS: [M + H] < ⁺ > = 721)

Example  34: Compound 34 of  synthesis

Compound 34 was prepared in the same manner as Compound 1 except for the intermediate A10 and 11,11-dimethyl-5,11-dihydroindeno [l, 2-b] carbazole instead of the intermediate A5 and diphenylamine. (Yield 75%, MS: [M + H] < ⁺ > = 787)

Example  35: Compound Thirty-five  synthesis

Compound 35 was prepared in the same manner as Compound 1 except for the intermediate A5 and the intermediate A10 and 5-phenyl-5,12-dihydroindolo [3,2-a] carbazole instead of diphenylamine. (Yield: 79%, MS: [M + H] < ⁺ > = 836)

Example  36: Compound Of 36  synthesis

Compound 36 was prepared in the same manner as in the preparation of Compound 1 except for Intermediate A5 and Intermediate A11 instead of diphenylamine and N-phenyl- [1,1'-biphenyl] -4-amine. (Yield 70%, MS: [M + H] < ⁺ > = 749)

Example  37: Compound 37  synthesis

Compound 37 was prepared in the same manner as Compound 1 except for Intermediate A5 and Intermediate A11 and 9H-carbazole in place of diphenylamine. (Yield: 73%, MS: [M + H] < ⁺ > = 671)

Example  38: Compound 38 of  synthesis

Compound 38 was prepared in the same manner as Compound 1 except for the intermediate A5 and 7,7-dimethyl-5,7-dihydroindeno [2,1-b] carbazole instead of the intermediate A11 and diphenylamine. (Yield 76%, MS: [M + H] < ⁺ > = 787)

Example  39: Compound 39 of  synthesis

Compound 39 was prepared in the same manner as Compound 1 except for the intermediate A5 and the intermediate A11 and 8,8-dimethyl-5,8-dihydroindeno [2,1-c] carbazole instead of diphenylamine. (Yield: 79%, MS: [M + H] < ⁺ > = 787)

Example  40: Compound 40's  synthesis

Compound 40 was prepared in the same manner as Compound 1 except for the intermediate A5 and the intermediate A11 and 5-phenyl-5,12-dihydroindolo [3,2-a] carbazole instead of diphenylamine. (Yield: 77%, MS: [M + H] < ⁺ > = 836)

Example  41: Compound 41 of  synthesis

Compound 41 was prepared in the same manner as Compound 1 except for Intermediate A12 except for Intermediate A5. (Yield 69%, MS: [M + H] < ⁺ > = 643)

Example  42: Compound 42  synthesis

Was prepared in the same manner as in the preparation of Compound 1 except for the intermediate A12 and the intermediate A12 instead of the intermediate A5 and N - ([1,1'-biphenyl] -4-yl) - [1,1'-biphenyl] Compound 42 was prepared. (Yield: 75%, MS: [M + H] < ⁺ > = 795)

Example  43: Compound 43  synthesis

Compound 43 was prepared in the same manner as Compound 1 except for Intermediate A5 and Intermediate A12 and 9H-carbazole in place of diphenylamine. (Yield: 74%, MS: [M + H] < ⁺ > = 641)

Example  44: Compound 44 of  synthesis

Compound 44 was prepared in the same manner as Compound 1 except for the intermediate A5 and the intermediate A12 and 7,7-dimethyl-5,7-dihydroindeno [2,1-b] carbazole instead of diphenylamine. (Yield 79%, MS: [M + H] < ⁺ > = 757)

Example  45: Compound 45  synthesis

Compound 45 was prepared in the same manner as Compound 1 except that Intermediate A5 and Intermediate A12 and 5-phenyl-5,12-dihydroindolo [3,2-a] carbazole were used instead of diphenylamine. (Yield: 77%, MS: [M + H] < ⁺ > = 806)

Example  46: Compound 46 of  synthesis

Compound 46 was prepared in the same manner as Compound 1 except for Intermediate A13 except Intermediate A5. (Yield 70%, MS: [M + H] < ⁺ > = 643)

Example  47: Compound 47 of  synthesis

Except that the intermediate A5 and the intermediate A13 in place of the diphenylamine and the compound 1 except for N - ([1,1'-biphenyl] -4-yl) -9,9-dimethyl-9H-fluoren- Compound 47 was prepared in the same manner. (Yield: 73%, MS: [M + H] < ⁺ > = 835)

Example  48: Compound 48 of  synthesis

Compound 48 was prepared in the same manner as Compound 1 except for Intermediate A13 and 9H-carbazole, instead of Intermediate A5 and diphenylamine. (Yield: 75%, MS: [M + H] < ⁺ > = 641)

Example  49: Compound 49 of  synthesis

Compound 49 was prepared in the same manner as in the preparation of Compound 1 except for Intermediate A5 and Intermediate A13 and 12,12-dimethyl-11,12-dihydroindeno [2,1-a] carbazole instead of diphenylamine. (Yield: 77%, MS: [M + H] < ⁺ > = 757)

Example  50: Compound 50's  synthesis

Compound 50 was prepared in the same manner as Compound 1 except that Intermediate A5 and Intermediate A13 and 5-phenyl-5,7-dihydroindolo [2,3-b] carbazole were used instead of diphenylamine. (Yield: 75%, MS: [M + H] < ⁺ > = 806)

Example  51: Compound 51 of  synthesis

Compound 51 was prepared in the same manner as in the preparation of Compound 1 except for Intermediate A5 and Intermediate A14 and di ([1,1'-biphenyl] -4-yl) amine instead of diphenylamine. (Yield 70%, MS: [M + H] < ⁺ > = 718)

Example  52: Compound 52  synthesis

Compound 52 was prepared in the same manner as Compound 1 except for Intermediate A5 and Intermediate A14 and 9H-carbazole in place of diphenylamine. (Yield: 73%, MS: [M + H] < ⁺ > = 564)

Example  53: Compound 53  synthesis

Compound 53 was prepared in the same manner as Compound 1 except for the intermediate A5 and the intermediate A14 and 7H-benzo [c] carbazole instead of diphenylamine. (Yield: 72%, MS: [M + H] < ⁺ > = 614)

Example  54: Compound 54  synthesis

Compound 54 was prepared in the same manner as Compound 1 except for the intermediate A5 and the intermediate A14 and 7,7-dimethyl-5,7-dihydroindeno [2,1-b] carbazole instead of diphenylamine. (Yield: 76%, MS: [M + H] < ⁺ > = 680)

Example  55: Compound 55  synthesis

Compound 55 was prepared in the same manner as Compound 1 except that Intermediate A5 and Intermediate A14 and 5-phenyl-5,12-dihydroindolo [3,2-a] carbazole were used instead of diphenylamine. (Yield: 79%, MS: [M + H] < ⁺ > = 729)

Example  56: Compound 56  synthesis

Except that the intermediate A5 and the intermediate A15 instead of diphenylamine and the compound 1 except for N - ([1,1'-biphenyl] -4-yl) -9,9-dimethyl-9H-fluoren- Compound 56 was prepared in the same manner. (Yield: 73%, MS: [M + H] < ⁺ > = 758)

Example  57: Compound 57 of  synthesis

Compound 57 was prepared in the same manner as Compound 1 except for Intermediate A5 and Intermediate A15 and 9H-carbazole in place of diphenylamine. (Yield: 74%, MS: [M + H] < ⁺ > = 564)

Example  58: Compound 58 of  synthesis

Compound 58 was prepared in the same manner as in the preparation of Compound 1 except for Intermediate A5 and Intermediate A15 and 12,12-dimethyl-11,12-dihydroindeno [2,1-a] carbazole instead of diphenylamine. (Yield: 72%, MS: [M + H] < ⁺ > = 680)

Example  59: Compound 59  synthesis

Compound 59 was prepared in the same manner as in the preparation of Compound 1 except for Intermediate A5 and Intermediate A15 instead of diphenylamine and 5-phenyl-5,12-dihydroindolo [3,2-a] carbazole. (Yield: 72%, MS: [M + H] < ⁺ > = 729)

Experimental Example 1

A thin glass substrate coated with ITO (indium tin oxide) at a thickness of 1,300 Å was immersed in distilled water containing detergent and washed with ultrasonic waves. At this time, a Fischer Co. product was used as a detergent, and distilled water, which was filtered with 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.

The following hexanitrile hexaazatriphenylene (HAT) compound was thermally vacuum deposited on the prepared ITO transparent electrode to a thickness of 500 Å to form a hole injection layer. The HT1 compound was thermally vacuum deposited on the hole injection layer to a thickness of 800 Å, and HT2 compound was vacuum deposited thereon to a thickness of 500 Å to form a hole transport layer. Compound 1 and compound H2 of Example 1 were co-deposited with the phosphorescent dopant Dp at a weight ratio shown in Table 1 as a host on the hole transport layer to form a 350Å thick light emitting layer. An ET1 material was vacuum deposited on the light emitting layer to form a hole blocking layer, and an ET2 material and LiQ (Lithium Quinolate) were vacuum deposited on the hole blocking layer at a weight ratio of 1: 1 to form an electron transport layer of 250 ANGSTROM . Lithium fulleride (LiF) was sequentially deposited on the electron transporting layer to a thickness of 10 Å, and aluminum was deposited thereon to a thickness of 1000 Å to form a cathode.

The deposition rate of the organic material was maintained at 0.4 to 0.7 Å / sec, the lithium fluoride at the cathode was maintained at a deposition rate of 0.3 Å / sec, and the deposition rate of aluminum was maintained at 2 Å / sec. ^-7 to 5 x 10 < ^-8 > torr.

The voltage, efficiency and lifetime of the organic light-emitting device thus fabricated were measured, and the results are shown in Table 1 below.

Experimental Examples 2 to 16

The organic light emitting devices of Experimental Examples 2 to 16 were produced 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 of Example 1 as the phosphorescent dopant in the formation of the light emitting layer. Respectively. In this case, when a mixture of two kinds of compounds is used as a host, the parenthesized means the weight ratio between the host compounds, and the H2 substance is as described above.

The voltage, efficiency and lifetime of the organic light emitting device thus manufactured were measured by the same method as in Experimental Example 1, and the results are shown in Table 1 below.

Comparative Experimental Examples 1 to 5

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that the compound described in Table 1 was used in an amount of the base material instead of the compound 1 of Example 1. In the following Table 1, C1 to C3 mean the following compounds, respectively. In this case, when a mixture of two kinds of compounds is used as the host, the parentheses indicate the weight ratio between the host compounds.

The voltage, efficiency, and lifetime characteristics were measured by applying current to the organic light emitting device manufactured in the same manner as in Experimental Example 1. The results are shown in Table 1 below.

Host
matter Voltage
(V @ 10 mA / cm ² ) efficiency
(cd / A @ 10mA / cm 2) Color coordinates
(x, y) life span
(T95, h,
@ 20 mA / cm ² ) Experimental Example 1 Compound 1: H2
(50:50) 4.4 81 0.34, 0.61 96 Experimental Example 2 Compound 4: H2
(50:50) 4.3 78 0.35, 0.62 97 Experimental Example 3 Compound 6: H2
(50:50) 4.3 79 0.35, 0.62 92 Experimental Example 4 Compound 16: H2
(50:50) 4.4 80 0.34, 0.61 95 Experimental Example 5 Compound 36: H2
(50:50) 4.5 79 0.35, 0.62 91 Experimental Example 6 Compound 42: H2
(50:50) 4.4 80 0.34, 0.62 90 Experimental Example 7 Compound 46: H2
(50:50) 4.5 83 0.35, 0.63 93 Experimental Example 8 Compound 51: H2
(50:50) 4.5 85 0.35, 0.62 92 Experimental Example 9 Compound 53: H2
(50:50) 4.3 82 0.35, 0.63 90 Experimental Example 10 Compound 58: H2
(50:50) 4.4 84 0.36, 0.62 89 Experimental Example 11 Compound 3 4.2 59 0.35, 0.61 51 Experimental Example 12 Compound 9 4.1 58 0.34, 0.61 50 Experimental Example 13 Compound 10 4.0 60 0.35, 0.62 55 Experimental Example 14 Compound 20 4.1 61 0.35, 0.62 54 Experimental Example 15 Compound 44 4.2 60 0.35, 0.61 56 Experimental Example 16 Compound 48 4.1 62 0.34, 0.61 53 Experimental Example 17 Compound 50 4.0 59 0.35, 0.62 55 Experimental Example 18 Compound 54 4.3 63 0.34, 0.62 53 Experimental Example 19 Compound 57 4.3 64 0.35, 0.60 52 Comparative Experimental Example 1 C1: H2
(50:50) 4.20 55 0.35, 0.61 80 Comparative Experimental Example 2 C1 4.00 50 0.35, 0.61 45 Comparative Experimental Example 3 C2: H2
(50:50) 4.23 71 0.34, 0.61 46 Comparative Experimental Example 4 C2 4.10 58 0.35, 0.62 33 Comparative Experiment Example 5 Compound C3: H2
(50:50) 5.1 56 0.35, 0.62 37

In Table 1, T95 represents the time required for the luminance to be reduced to 95% from the initial luminance.

As shown in Table 1, it was confirmed that the compound according to the present invention is a host material having higher efficiency and longevity than the compound C1, which is a conventional green luminescent host material. In addition, compared to compound C2, it showed about twice the lifetime characteristics and exhibited low voltage and long life characteristics in comparison with compound C3. It can be confirmed that the voltage and the life time difference show depending on the substitution position of the dibenzofurane of the compound of the example.

Comparing with Comparative Example 3 or 4, it was confirmed that triazine, which is a hetero-substituent, is located at position 1 of dibenzofurane rather than position 2, which shows advantages in terms of efficiency and life span. When the compound of Comparative Example 5 was compared with the compound of the present invention, the voltage difference was large depending on the position of the substituent. This indicates that in view of the stability and balance of accepting holes and electrons from the adjacent layers of the device, the structural dibenzofuran The presence of substituents at positions 1 and 6 rather than positions 4 and 6 showed elemental strength.

While the present invention has been described in connection with what is presently considered to be preferred embodiments, it is to be understood that the invention is not limited to the disclosed embodiments, but, on the contrary, is intended to cover various modifications and equivalent arrangements included within the spirit and scope of the appended claims.

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 (13)

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

In Formula 1,
X < ₁ > is O or S,
Y ₁ to Y ₃ are each independently N or CR ₃ , at least one of Y ₁ to Y ₃ is N,
L ₁ and L ₂ are each independently a bond; Substituted or unsubstituted C _6-60 arylene; Or substituted or unsubstituted C _2-60 heteroarylene containing at least one heteroatom selected from the group consisting of O, N, Si and S,
Ar ₁ and Ar ₂ are each independently a substituted or unsubstituted C _6-60 aryl; Or substituted or unsubstituted C _2-60 heteroaryl containing 1 to 3 heteroatoms selected from the group consisting of N, O and S,
Ar ₃ is N (Ar ₁₁ ) (Ar ₁₂ ); Or substituted or unsubstituted C _2-60 heteroaryl containing 1 to 3 hetero atoms selected from the group consisting of N, O and S, the atom bonding to L ₂ is a hetero atom,
Wherein Ar ₁₁ and Ar ₁₂ are each independently a substituted or unsubstituted C _6-60 aryl; Or substituted or unsubstituted C _2-60 heteroaryl containing 1 to 3 heteroatoms selected from the group consisting of N, O and S,
R ₁ to R ₃ are each independently hydrogen; heavy hydrogen; halogen; Cyano; Amino; Substituted or unsubstituted C _1-6 alkyl; C _1-60 haloalkyl; Substituted or unsubstituted C _1-60 alkoxy; Substituted or unsubstituted C _1-60 haloalkoxy; Substituted or unsubstituted C _3-60 cycloalkyl; Substituted or unsubstituted C _2-60 alkenyl; Substituted or unsubstituted C _6-60 aryl; Substituted or unsubstituted C _6-60 aryloxy; Or a substituted or unsubstituted C _2-60 heterocyclic group containing at least one heteroatom selected from the group consisting of N, O and S,
a1 and a2 are each independently an integer of 0 to 3;
The method according to claim 1,
Y ₁ and Y ₂ are N, Y ₃ is CH,
Y ₁ and Y ₃ are N, Y ₂ is CH, or
Y ₁ , Y ₂ and Y ₃ are N, compound.
The method according to claim 1,
L ₁ and L ₂ are each independently selected from the group consisting of a bond or a group consisting of:

.
The method according to claim 1,
Ar ₁ and Ar ₂ are each independently any one selected from the group consisting of:

In the above,
Z ₁ and Z ₂ are each independently hydrogen; heavy hydrogen; halogen; Cyano; Amino; C _1-20 alkyl; C _1-20 haloalkyl; Or C _6-20 aryl,
c1 and c2 are each independently an integer of 0 to 3;
5. The method of claim 4,
Ar ₁ and Ar ₂ are each independently any one selected from the group consisting of:

The method according to claim 1,
Ar ₃ is any one selected from the group consisting of:

In the above,
X ₂ and X ₃ are each independently O, S, NZ ₁₃ , or CZ ₁₄ Z ₁₅ ,
Ar ₁₁ and Ar ₁₂ each independently represent a substituted or unsubstituted C _6-20 aryl; Or substituted or unsubstituted C _2-20 heteroaryl containing 1 to 3 hetero atoms selected from the group consisting of N, O and S,
Z ₁₁ to Z ₁₅ each independently represent hydrogen; heavy hydrogen; halogen; Cyano; Amino; C _1-20 alkyl; C _1-20 haloalkyl; Or C _6-20 aryl,
n1 and n2 are each independently an integer of 0 to 3;
The method according to claim 6,
Ar ₃ is any one selected from the group consisting of:

.
The method according to claim 1,
Wherein R ₁ to R ₃ are hydrogen.
The method according to claim 1,
Wherein said compound is any one selected from the group consisting of:

A first electrode; A second electrode facing the first electrode; And at least one organic compound layer provided between the first electrode and the second electrode,
Wherein at least one of the organic layers comprises a compound according to any one of claims 1 to 9.
11. The method of claim 10,
The organic compound layer containing the compound may include a hole injection layer; A hole transport layer; Or a layer which simultaneously injects holes and transports holes.
11. The method of claim 10,
The organic compound layer containing the compound may include an electron injection layer; An electron transport layer; Or an electron injection and electron transporting layer simultaneously.
11. The method of claim 10,
Wherein the organic compound layer containing the compound is a light emitting layer.

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