KR101857703B1 - Novel hetero-cyclic compound and organic light emitting device comprising the same - Google Patents

Abstract

The present invention provides a novel heterocyclic compound and an organic light-emitting device using the same. A compound represented by 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

[0001] The present invention relates to novel heterocyclic compounds and organic light emitting devices using the same. More particularly,

The present invention relates to a novel heterocyclic 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 heterocyclic 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 is O, S, or SiR < ₅ > R < ₆ &

R _1a to R _4a each independently represent L ₁ -HAr ₁ or A _1, provided that at least one of R _1a to R _4a is L ₁ -HAr ₁ ,

R _1b to R _4b are each independently L ₂ -HAr ₂ or A ₂ , at least one of R _1b to R _4b is L ₂ -HAr ₂ ,

When R _1a is L ₁ -HAr ₁ , R _1b is not L ₂ -HAr ₂ ,

When R _2a is L ₁ -HAr ₁ , R _2b is not L ₂ -HAr ₂ ,

When R _3a is L ₁ -HAr ₁ , R _3b is not L ₂ -HAr ₂ ,

When R _4a is L ₁ -HAr ₁ , then R _4b is not L ₂ -HAr ₂ ,

L ₁ and L ₂ each independently represent a direct 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, and the substituted or unsubstituted carbazolylene is excluded ,

HAr ₁ and HAr ₂ are each independently selected from the group consisting of at least two or more of N,

X ₁ to X ₃ are each independently N or CR ₇ ,

A ₁ , A ₂ , R ₅ to R ₇ , R ₁₁ and R ₁₂ each independently represent hydrogen; heavy hydrogen; halogen; Cyano; Amino; Substituted or unsubstituted C _1-6 alkyl; Substituted or unsubstituted C _1-6 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,

n1 is an integer of 0 to 3;

은 제외된다. Preferably, when R _1a is L ₁ -HAr ₁ , R _2b is L ₂ -HAr ₂ , or R _2a is L ₁ -HAr ₁ and R _1b is L ₂ -HAr ₂ , HAr ₁ and HAr ₂ in

Are excluded.

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. Particularly, the compound represented by the above-mentioned formula (1) can be used as a material for the light emitting layer.

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.
Figures 3 to 5 show PL _max data for compounds according to the present invention.

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

또는

는 다른 치환기에 연결되는 결합을 의미하고, 단일 결합은 L₁ 및 L₂로 표시되는 부분에 별도의 원자가 존재하지 않은 경우를 의미한다. In the present specification,

or

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 ₁ and L ₂ .

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, X may be O, S, Si (CH ₃ ) ₂ , or Si (C ₆ H ₅ ) ₂ . Alternatively, X may be O.

Also,

One of R _1a to R _4a is L ₁ -HAr ₁ , the other is A ₁ ,

One of R _1b to R _4b may be L ₂ -HAr ₂ , and the other may be A ₂ .

E.g,

R _1a is L ₁ -HAr ₁ and R _2b is L ₂ -HAr ₂ ;

R _1a is L ₁ -HAr ₁ and R _3b is L ₂ -HAr ₂ ;

R _1a is L ₁ -HAr ₁ and R _4b is L ₂ -HAr ₂ ;

R _2a is L ₁ -HAr ₁ and R _3b is L ₂ -HAr ₂ ;

R _2a is L ₁ -HAr ₁ and R _4b is L ₂ -HAr ₂ ; or

R _3a may be L ₁ -HAr ₁ , and R _4b may be L ₂ -HAr ₂ .

L ₁ and L ₂ are each independently a direct bond; Or substituted or unsubstituted C _6-60 arylene.

Alternatively, L ₁ and L ₂ may each independently be a direct bond,

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

Also, at least one of L ₁ and L ₂ may be a direct bond. For example, L &_lt; ₁ > is a direct bond; L ₂ is a direct bond; Or L < _{1 >} and L < ₂ > may be a direct bond.

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

In the above,

R ₇ , R ₁₁ and R ₁₂ are each independently hydrogen; heavy hydrogen; halogen; Cyano; Amino; Substituted or unsubstituted C _1-20 alkyl; Substituted or unsubstituted C _1-20 haloalkyl; Substituted or unsubstituted C _6-20 aryl; Or a substituted or unsubstituted C _2-20 heterocyclic group containing at least one heteroatom selected from the group consisting of N, O and S.

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

In the above,

R ₁₁ and R ₁₂ are each independently hydrogen; heavy hydrogen; halogen; Cyano; Amino; Substituted or unsubstituted C _1-20 alkyl; Substituted or unsubstituted C _1-20 haloalkyl; Substituted or unsubstituted C _6-20 aryl; Or a substituted or unsubstituted C _2-20 heterocyclic group containing at least one heteroatom selected from the group consisting of N, O and S.

은 제외된다. R_1a가 L₁-HAr₁이고, R_2b가 L₂-HAr₂이거나, 또는 R_2a가 L₁-HAr₁이고, R_1b가 L₂-HAr₂인 화합물에서, HAr₁ 및 HAr₂로 치환 또는 비치환된 트리아지닐기가 포함되는 경우, 본 발명에 따른 화합물을 적용한 유기 발광 소자에 비하여, 상대적으로 전자가 잘 주입되지 않아 정공과 전자간의 balance가 틀어져 구동 전압이 높고 효율이 저하될 수 있다.Provided that when R _1a is L ₁ -HAr ₁ , R _2b is L ₂ -HAr ₂ , or R _2a is L ₁ -HAr ₁ and R _1b is L ₂ -HAr ₂ , then HAr ₁ and HAr ₂

Are excluded. In compounds wherein R _1a is L ₁ -HAr ₁ , R _2b is L ₂ -HAr ₂ , or R _2a is L ₁ -HAr ₁ and R _1b is L ₂ -HAr ₂ , substitution with HAr ₁ and HAr ₂ Or an unsubstituted triazinyl group, compared with the organic light emitting device using the compound according to the present invention, electrons are not injected relatively well, and the balance between holes and electrons is distorted, resulting in high driving voltage and inefficiency.

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

A ₁ and A ₂ are each independently selected from the group consisting of hydrogen; heavy hydrogen; halogen; Cyano; Amino; Substituted or unsubstituted C _1-20 alkyl; Substituted or unsubstituted C _1-20 haloalkyl; Or substituted or unsubstituted C _6-20 aryl.

For example, A < ₁ > and A < ₂ > may be hydrogen.

Herein, n1 represents the number of R < ₁₁ >, and when n1 is 2 or more, two or more R < ₁₁ > may be the same or different.

Further, the compound may be any one of the compounds represented by the following general formulas 1-1 to 1-6:

[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

[Formula 1-5]

[Chemical Formula 1-6]

In the above formulas 1-1 to 1-6,

X, L ₁ , L ₂ , HAr ₁ and HAr ₂ are as defined in the above formula (1).

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 L ₁ -HAr ₁ and L ₂ -HAr ₂ substituents are asymmetrically linked to a core such as dibenzofurane, and thus the organic light emitting device using the same has a high efficiency, a low driving voltage, High brightness and long life.

Meanwhile, the compounds represented by the above Formulas 1-1 to 1-6 can be prepared, for example, according to the following reaction schemes 1 to 6, respectively. The above production method can be more specific in the production example to be described later.

[Reaction Scheme 1]

[Reaction Scheme 2]

[Reaction Scheme 3]

[Reaction Scheme 4]

[Reaction Scheme 5]

[Reaction Scheme 6]

In the above Reaction Schemes 1 to 6, L ₁ , L ₂ , HAr ₁ and HAr ₂ are as defined in Formula 1 above.

The compound represented by the formula (1) can be prepared by appropriately substituting the starting material according to the structure of the compound to be prepared with reference to the Schemes 1 to 6.

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.

For example, the organic layer may include a light emitting layer, and the light emitting layer may include a compound represented by the general formula (1). Specifically, the compound represented by Formula 1 may be included as a host.

In particular, the compound of the present invention is characterized in that the PL peak max is shorter, the HOMO level is higher, and the band gap is larger than that of conventional host compounds.

At this time, the light emitting layer may further include a phosphorescent dopant compound. The usable phosphorescent dopant materials are as described below, but are not limited thereto.

The light emitting layer may further include at least one known P-type host compound selected from the group consisting of an anthracene derivative, a pyrene derivative, a naphthalene derivative, a pentacene derivative, a phenanthrene derivative, a fluoranthene derivative and a carbazole derivative But is not limited thereto.

When the light emitting layer further includes the P-type host compound in addition to the N-type host represented by Formula 1, the organic light emitting device may exhibit exciplex characteristics.

Further, the organic material layer may include the electron transporting layer, the electron injection layer, or a layer that simultaneously performs electron transport and electron injection, and the electron transport layer, the electron injection layer, 1 < / RTI >

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.

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 with a low work function followed by an aluminum layer or 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 the 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 compound 1

1) Preparation of intermediate 1-1d

(A) Preparation of intermediate 1-1a

(50 g, 0.26 mol) and (3-chloro-2-fluorophenyl) boronic acid (46.1 g, 0.21 mol) were dissolved in tetrahydrofuran (500 mL), 1.5M potassium carbonate aqueous solution (400 mL) was added, and bis (tri-tert-butylphosphine) palladium (0) (1.35 g, 2.36 mmol) was added and the mixture was heated with stirring for 1 hour. The mixture was recrystallized from hexane and then dried to obtain Intermediate 1-1a (49.8 g, yield 79%, MS: < RTI ID = 0.0 > [M + H] < ⁺ > = 239).

(B) Preparation of intermediate 1-1b

Intermediate 1-1a (49.8 g, 0.21 mol) and calcium carbonate (57.7 g, 0.42 mol) were dissolved in N-methyl-2-pyrrolidone (200 mL) and heated and stirred for 2 hours in a 500 mL round bottom flask . The temperature was lowered to room temperature and reprecipitated in water. (31.8 g, yield 70%, MS: [M + H] +) was prepared in the same manner as in Reference Example 1, except that the reaction mixture was distilled under a reduced pressure and the reaction mixture was diluted with dichloromethane, washed with water, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, recrystallized using ethanol, H] < ⁺ > = 219).

(C) Preparation of intermediate 1-1c

The intermediate 1-1b (31.8 g, 0.15 mol) was dissolved in acetonitrile (150 mL), and calcium carbonate (33.1 g, 0.24 mol) was dissolved in water (150 mL) Nonafluorobutanesulfonyl fluoride (28.7 mL, 0.16 mol) was slowly added dropwise over 30 minutes. 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 1-1c (53.3 g, yield 73% , MS: [M + H] < ⁺ > = 501).

(D) Preparation of intermediate 1-1d

Intermediate 1-1c (53.3 g, 0.11 mol), 4,4,5,5-tetramethyl- [1,3,2] -dioxaborolane (28.4 g, 17.85 mol), Pd (dppf) Cl ₂ 0.78 g, 1.06 mmol) and KOAc (31.3 g, 0.32 mol) were added to dioxane (650 mL) and stirred at reflux for 8 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 to obtain Intermediate 1-1d (30.1 g, yield 86%, MS: [M + H ] ⁺ = 329).

2) Synthesis of the compound of Intermediate 1-1f

(A) Preparation of intermediate 1-1e

(30.1 g, 91.6 mmol) and 2-chloro-4,6-diphenylpyrimidine (1a, 24.4 g, 91.6 mmol) were dissolved in tetrahydrofuran (200 mL) in a 500 mL round- , And then 1.5M potassium carbonate aqueous solution (100 mL) was added thereto. Tetrakis- (triphenylphosphine) palladium (1.06 g, 0.92 mmol) was added thereto, followed by heating and stirring for 11 hours. The mixture was recrystallized from dichloromethane and then dried to obtain Intermediate 1-1e (32.1 g, yield 81%, MS : [M + H] < ⁺ > = 433).

(B) Preparation of Intermediate 1-1f

Intermediate 1-1e (32.1 g, 74.1 mmol) , 4,4,5,5- tetramethyl- [l, 3,2] dioxaborolane (19.8 g, 77.9 mmol), Pd (dba) 2 (1.28 g, 2.22 mmol), PCy ₃ (1.25 g, 4.45 mmol) and KOAc (21.8 g, 0.22 mol) were placed in dioxane (400 mL) and stirred at reflux for 13 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, recrystallized using ethanol, dried and purified to obtain Intermediate 1-1f (29.5 g, yield 76% [M + H] < ⁺ > = 525).

3) Synthesis of Compound 1

(15 g, 28.6 mmol), 4 - ([1,1'-biphenyl] -4-yl) -2-chloro-6-phenylpyridine (1b, 9.81 g, 28.6 mmol) was dissolved in tetrahydrofuran (150 mL), followed by the addition of 1.5 M aqueous potassium carbonate solution (70 mL), bis (tri-tert-butylphosphine) palladium (0) (0.15 g, 0.29 mmol ), And the mixture was heated and stirred for 9 hours. Lower the temperature to room temperature, filter and wash with water to remove the base. (13.4 g, yield 66%, MS: [M + H] < ⁺ > = 705).

Manufacturing example  2: Synthesis of Compound 2

The compound 2c was prepared in the same manner as the compound 1 except that 2- (4-bromophenyl) -4,6-di phenylpyridine (1c) was used instead of the intermediate 1b (8.9 g, yield 69%, MS: [M + H] < ⁺ > = 705).

Manufacturing example  3: Synthesis of Compound 3

1) Compound Synthesis of Intermediate 1-1h

(A) Preparation of Intermediate 1-1g

(10.5 g, yield 71%, MS: [M + H] < ⁺ > = 509) was prepared in the same manner as Intermediate 1-1e, except that Intermediate 1c was used instead of Intermediate 1a. .

(B) Preparation of intermediate 1-1h

Intermediate 1-1h was prepared in the same manner as Intermediate 1-1f except that Intermediate 1-1e was replaced by Intermediate 1-1e (9.1 g, yield 71%, MS: [M + H] ⁺ = 601).

2) Synthesis of Compound 3

(7.8 g, yield 73%, MS: [M + H] +) was prepared in the same manner as in the preparation of Compound 1, except that Intermediate 1-1h and Intermediate 1a were used in place of Intermediate 1-1f and Intermediate 1b. H] < ⁺ > = 705).

Manufacturing example  4: Preparation of compound 4

1) Synthesis of the compound of Intermediate 2-1b

(A) Preparation of intermediate 2-1a

4-Chlorodibenzofuran (75 g, 0.37 mol) was dissolved in DMF (700 mL) in a 1000 mL round-bottomed flask under nitrogen atmosphere, NBS (69.2 g, 0.39 mol) , And the mixture was stirred at room temperature for 3 hours. Thereafter, the solution was reduced in pressure, dissolved in ethyl acetate, washed with water with water, the organic layer was separated, and the solvent was removed by decompression. This was subjected to column chromatography to obtain Intermediate 2-1a (92.5 g, yield 89%, MS: [M + H] ⁺ = 280).

(B) Preparation of intermediate 2-1b

Intermediate 2-1a (92.5 g, 0.33 mol) , 4,4,5,5- tetramethyl- [l, 3,2] dioxaborolane (87.9 g, 0.35 mol), Pd (dppf) Cl 2 ( 2.41 g, 3.30 mmol) and KOAc (97.1 g, 0.99 mol) were added to dioxane (1000 mL) and stirred at reflux for 9 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 containing the product was concentrated under reduced pressure, recrystallized using ethanol, dried and purified to obtain Intermediate 2-1b (115 g, yield 67%, MS: [M + H] < ⁺ > = 329).

2) Synthesis of compound of Intermediate 2-1d

(A) Preparation of intermediate 2-1c

Intermediate 2-1c was prepared in the same manner as Intermediate 1-1e except that Intermediate 1-lb was used instead of Intermediate 1-ld (38.5 g, yield 73%, MS: [M + H] ⁺ = 434).

(B) Preparation of intermediate 2-1d

(30.8 g, yield 66%, MS: [M + H] < + >) was prepared in the same manner as Intermediate 1-1f except for using Intermediate 2-1c instead of Intermediate 1-1e. ⁺ = 525).

3) Synthesis of Compound 4

3-yl) -4-chloro-6-phenyl-1,3,5-triazine (2a) instead of Intermediate 2-1d and Intermediate 1b instead of Intermediate 1-1f. (32.9 g, yield 79%, MS: [M + H] < ⁺ > = 706) was prepared in the same manner as Compound 1 was prepared.

Manufacturing example  5: Preparation of compound 5

1) Synthesis of the compound of Intermediate 2-2b

(A) Preparation of intermediate 2-2a

Preparation of intermediate 2-2a was carried out in the same manner as in the preparation of intermediate 2-1c, except that 2-chloro-4,6-diphenyl-1,3,5-triazine (2b) was used instead of intermediate 1a. (40.2 g, 76% yield, MS: [M + H] < ⁺ > = 434).

(B) Preparation of intermediate 2-2b

Intermediate 2-2b was prepared in the same manner as Intermediate 2-1b except that Intermediate 2-2a was used instead of Intermediate 2-1c (34.1 g, yield 70%, MS: [M + H] < ⁺ = 526).

2) Synthesis of Compound 5

(Dibenzo [b, d] furan-l-yl) -6-phenyl-l, 3,5-triazine (2c) instead of Intermediate 2-2b and Intermediate 2a instead of Intermediate 2-1d (11.6 g, yield 74%, MS: [M + H] < ⁺ > = 721) was prepared in the same manner as compound 3 was prepared.

Manufacturing example  6: Preparation of Compound 6

Compound 3 was prepared in a similar manner to Intermediate 2-1b except that 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine (2d) was used instead of Intermediate 2-2b and Intermediate 2a instead of Intermediate 2-1d. (9.0 g, yield 70%, MS: [M + H] < ⁺ > = 707).

Manufacturing example  7: Preparation of Compound 7

4-yl) -6- (4-chlorophenyl) -2-phenylpyridine (2f) was used in place of Intermediate 2-2b and Intermediate 2a instead of Intermediate 2-1d (11.3 g, yield 71%, MS: [M + H] < ⁺ > = 782) in the same manner as the compound 3 was prepared.

Manufacturing example  8: Preparation of compound 8

1) Synthesis of compound of intermediate 2-3b

(A) Preparation of intermediate 2-3a

(38.1 g, yield 71%, MS: [M + H] ⁺ = 510) was prepared in the same manner as Intermediate 2-1c, except that Intermediate 2d was used instead of Intermediate 1a. ).

(B) Preparation of intermediate 2-3b

(29.3 g, yield 65%, MS: [M + H] < + >) was prepared in the same manner as Intermediate 2-1d, except that Intermediate 2-1c was used instead of Intermediate 2-1c. ⁺ = 602).

2) Synthesis of Compound 8

(24.4 g, yield 70%, MS: [M + H] +) was prepared in the same manner as Compound 3, except that Intermediate 2b was used instead of Intermediate 2-1d and Intermediate 2b was used instead of Intermediate 2a. H] < ⁺ > = 707).

Manufacturing example  9: Preparation of compound 9

1) Synthesis of the compound of Intermediate 3-1d

(A) Preparation of intermediate 3-1a

Intermediate 3-1a was prepared in the same manner as in the preparation of intermediate 1-1a except that 2-iodobenzene-1,3-diol (50 g, 0.21 mol) was used instead of 2-bromoresorcinol (38.9 g, yield 77%, MS: [M + H] < ⁺ > = 239).

(B) Preparation of intermediate 3-1b

Intermediate 3-1b was prepared in the same manner as Intermediate 1-1b except that Intermediate 1-a was used instead of Intermediate 1-1a (24.3 g, yield 68%, MS: [M + H] ⁺ = 219).

(C) Preparation of intermediate 3-1c

(37.8 g, yield 74%, MS: [M + H] < + >) was prepared in the same manner as Intermediate 1-1c, except that Intermediate 3-1b was used instead of Intermediate 1-1b. ⁺ = 500).

(D) Preparation of intermediate 3-1d

Intermediate 3-1d was prepared in the same manner as Intermediate 1d except that Intermediate 1-c was used instead of Intermediate 1-1c, (8.1 g, yield 88%, MS: [M + H] ⁺ = 329).

2) Synthesis of the compound of Intermediate 3-1f

(A) Preparation of intermediate 3-1e

Intermediate 3-1e was prepared in the same manner as Intermediate 1-1e except that Intermediate 3-1d was used instead of Intermediate 1d and Intermediate 2b was used in place of Intermediate 1b (9.3 g, yield 87%, MS : [M + H] < ⁺ > = 434).

(B) Preparation of intermediate 3-1f

Intermediate 3-1f was prepared in the same manner as Intermediate 1f except that Intermediate 1-e was used instead of Intermediate 1-e (9.9 g, yield 76%, MS: [M + H] ⁺ = 526).

3) Synthesis of Compound 9

(Dibenzo [b, d] furan-4-yl) -6-phenyl-1,3,5-triazine (3a) instead of Intermediate 3-1f and Intermediate 2c in place of Intermediate 2-2b Compound 9 was prepared (6.2 g, yield 90.5%, MS: [M + H] ⁺ = 721) in the same manner as compound 4 was prepared.

Manufacturing example  10: Preparation of compound 10

Except that 4 - ([1,1'-biphenyl] -4-yl) -2-chloroquinazoline (3b) was used instead of Intermediate 3-1f and Intermediate 2c in place of Intermediate 2-2b. (4.9 g, yield 88%, MS: [M + H] ⁺ = 680).

Manufacturing example  11: Preparation of compound 11

(A) Preparation of intermediate 3-2a

Intermediate 3-1c (15.0 g, 30.3 mmol) , 4,4,5,5- tetramethyl- [l, 3,2] dioxaborolane (16.0 g, 62.9 mmol), Pd (dba) 2 (0.52 g, 0.90 mmol), PCy ₃ (0.5 g, 1.80 mmol) and KOAc (8.82 g, 89.9 mmol) were added to dioxane (200 mL) and stirred at reflux for 15 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 containing the product was concentrated under reduced pressure, recrystallized using ethanol, dried and purified to obtain Intermediate 3-2a (8.3 g, yield 65%, MS: [M + H] < ⁺ > = 421).

(B) Preparation of Compound 7

Intermediate 3-2a (8.3 g, 19.8 mmol) and Intermediate 2b (10.6 g, 39.5 mmol) were dissolved in tetrahydrofuran (100 mL) in a 250 mL round bottom flask under a nitrogen atmosphere and a 1.5 M aqueous potassium carbonate solution (45 mL) (Tri-tert-butylphosphine) palladium (0) (0.50 g, 0.99 mmol) was added thereto, followed by heating and stirring for 6 hours. The temperature was lowered to room temperature, filtered, and washed with water to remove the base. (11.6 g, yield 93%, MS: [M + H] < ⁺ > = 631) was obtained by recrystallization using N-methyl-2-pyrrolidone.

Manufacturing example  12: Preparation of compound 12

1) Synthesis of compound of intermediate 3-3b

(A) Preparation of intermediate 3-3a

Instead of Intermediate 3-1c and Intermediate 2b in place of Intermediate 3-1d, 2,4-diphenyl-6- (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan- Synthesis of Intermediate 3-3a was carried out in the same manner as in the preparation of Intermediate 3-1e (7.3 g, yield 81%, yield: 83%), except that 1-phenylphenyl) -1,3,5-triazine MS: [M + H] < ⁺ > = 510).

(B) Preparation of intermediate 3-3b

Intermediate 3-3b was prepared (6.7 g, yield 77%, MS: [M + H]) in the same manner as in the preparation of Intermediate 1-1f, except that Intermediate 3-3a was used instead of Intermediate 1-1e. ⁺ = 602).

2) Synthesis of Compound 12

(7.2 g, yield 91%, MS: [M + H] < ⁺ > = 707) in the same manner as in the preparation of Compound 5, except that Intermediate 3-3b was used instead of Intermediate 2-3b. .

Manufacturing example  13: Preparation of compound 13

1) Synthesis of compound of intermediate 3-4b

Intermediate 3-4a was prepared in the same manner as Intermediate 3-1e except that Intermediate 1a was used instead of Intermediate 2b, and then Intermediate 3-4b was obtained in the same manner as Intermediate 3-1f, (9.2 g, MS: [M + H] < ⁺ > = 525).

2) Synthesis of Compound 13

(8.0 g, yield 64%, MS: [M + H] < ⁺ > = 706) was prepared in the same manner as in the preparation of Compound 5, except that Intermediate 3-4b was used instead of Intermediate 2-3b. .

Manufacturing example  14: Preparation of compound 14

(A) Preparation of intermediate 4-1a

Intermediate 4-1a was prepared in the same manner as Intermediate 2-2a except for using dibenzo [b, d] furan-3-ylboronic acid instead of Intermediate 2-1b and Intermediate 3a instead of Intermediate 2b (71.4 g, yield 88%, MS: [M + H] < ⁺ > = 490).

(B) Preparation of intermediate 4-1b

(71.4 g, 0.15 mol) was dissolved in 1400 mL of a mixed solution of acetic acid and sulfuric acid (95-96%) (v: v = 5: 5) and then NBS (28.6 g, 0.16 mol) The mixture was added to the mixture slowly 7 times, and the mixture was stirred at room temperature for 3 hours. After that, the reaction product was added to water, filtered, and washed with water and ethanol. (42.9 g, yield 52%, MS: [M + H] < ⁺ > = 568) was obtained by purification (recrystallization) using tetrahydrofuran and toluene.

(C) Preparation of intermediate 4-1c

Intermediate 4-1c was prepared in the same manner as Intermediate 3-1b except that Intermediate 4-1b was used instead of Intermediate 3-3a (34.9 g, yield 75%, MS: [M + H] ⁺ = 616).

(D) Preparation of Compound 14

(30.5 g, yield 74%, MS: [M + H] < ⁺ > = 721) was prepared in the same manner as in the preparation of Compound 5, except that Intermediate 4-1c was used instead of Intermediate 2b- .

Manufacturing example  15: Preparation of compound 15

(A) Preparation of intermediates 4-2a and 4-2b

Intermediate 4-2a was prepared in the same manner as Intermediate 2-2a except that dibenzo [b, d] furan-3-ylboronic acid was used in place of Intermediate 2-1b. Intermediate 4-2b was prepared (15.1 g, MS: [M + H] < ⁺ > = 478).

(B) Preparation of intermediate 4-2c

Intermediate 4-2c was prepared in the same manner as Intermediate 3-2b except that Intermediate 4-2b was used instead of Intermediate 3-3a (11.8 g, yield 71%, MS: [M + H] < ⁺ = 526).

(D) Preparation of compound 15

(10.1 g, yield 64%, MS: [M + H] < ⁺ > = 707) was prepared in the same manner as in the preparation of Compound 5, except that Intermediate 4-2c was used instead of Intermediate 2b- .

Manufacturing example  16: Preparation of compound 16

(A) Preparation of intermediates 4-3a and 4-3b

Intermediate 4-3a was prepared in the same manner as Intermediate 2-2a except that dibenzo [b, d] furan-3-ylboronic acid was used in place of Intermediate 2-1b, and then Intermediate 4- Intermediate 4-3b was prepared (10.7 g, MS: [M + H] < ⁺ > = 477).

(B) Preparation of intermediate 4-3c

Intermediate 4-3c was prepared in the same manner as Intermediate 3-3b except that Intermediate 3-3b was used instead of Intermediate 3-3a (8.4 g, yield 71%, MS: [M + H] < ⁺ = 525).

(D) Preparation of Compound 16

(7.6 g, yield 67%, MS: [M + H] < ⁺ > = 705) was prepared in the same manner as in the preparation of Compound 5, except that Intermediate 4-3c was used instead of Intermediate 2-3b. .

Manufacturing example  17: Preparation of compound 17

1) Synthesis of the compound of Intermediate 5-1d

(A) Preparation of intermediate 5-1a

(4-chloro-2-fluorophenyl) boronic acid was used in the place of (4-chloro-2-fluorophenyl) (40.4 g, yield 75%, MS: [M + H] < ⁺ > = 239).

(B) Preparation of intermediate 5-1b

Intermediate 5-1b was prepared in the same manner as Intermediate 1-1b except that Intermediate 5-1a was used instead of Intermediate 1-1a (26.8 g, yield 72%, MS: [M + H] ⁺ = 219).

(C) Preparation of intermediate 5-1c

Intermediate 5-1c was prepared in the same manner as Intermediate 1-1c except that Intermediate 5-1b was used instead of Intermediate 3-1b (50.1 g, yield 81%, MS: [M + H] < ⁺ = 500).

(D) Preparation of intermediate 5-1d

Intermediate 5-1d was prepared in the same manner as Intermediate 1-1d except that Intermediate 5-1c was used instead of Intermediate 1-1c (30.0 g, yield 91%, MS: [M + H] ⁺ = 329).

2) Synthesis of the compound of Intermediate 5-1f

(A) Preparation of intermediate 5-1e

Intermediate 5-1e was prepared in the same manner as Intermediate 2-2a except that Intermediate 5-1d was used instead of Intermediate 2-1b (17.1 g, yield 86%, MS: [M + H] ⁺ = 434).

(B) Preparation of intermediate 5-1f

Intermediate 5-1f was prepared in the same manner as Intermediate 1-1f except that Intermediate 1-1e was used instead of Intermediate 1-1e (13.6 g, yield 66%, MS: [M + H] < ⁺ = 526).

3) Synthesis of Compound 17

4-chloro-6-phenyl-1,3,5-triazine (5a) instead of Intermediate 5-1f and 2b in place of Intermediate 2-1d (8.2 g, yield 89%, MS: [M + H] < ⁺ > = 707) was prepared in the same manner as Compound 3 was prepared.

Manufacturing example  18: Preparation of compound 18

(Dibenzo [b, d] furan-3-yl) -6-phenyl-1,3,5-triazine (5b) was used instead of Intermediate 5-1f and 2b instead of Intermediate 2-1d (7.8 g, yield 83%, MS: [M + H] ⁺ = 721).

Manufacturing example  19: Preparation of compound 19

1) Synthesis of the compound of Intermediate 5-2b

(A) Preparation of intermediate 5-2a

Intermediate 5-2a was prepared in the same manner as Intermediate 1-1e except that Intermediate 1d and Intermediate 1a were used instead of Intermediate 5-1d and Intermediate 2b (15.2 g, yield 77%, MS : [M + H] < ⁺ > = 433).

(B) Preparation of intermediate 5-2b

(12.8 g, yield 69%, MS: [M + H] < + >) was prepared in the same manner as Intermediate 1-1f, except that Intermediate 5-2a was used instead of Intermediate 1-1e. ⁺ = 525).

2) Synthesis of Compound 19

Compound 3 was prepared except that 2- (4-bromophenyl) -4,6-diphenyl-1,3,5-triazine (5c) was used instead of intermediate 5-2b and 2b instead of intermediate 2-1d (7.0 g, yield 81%, MS: [M + H] < ⁺ > = 706).

Manufacturing example  20: Preparation of compound 20

(A) Preparation of intermediate 5-3a

Compound 3 was prepared except that 2-chloro-4- (4-chlorophenyl) -6-phenyl-1,3,5-triazine (5d) was used instead of Intermediate 5-2b and 2b instead of Intermediate 2-1d (6.5 g, yield 80%, MS: [M + H] < ⁺ > = 665) was prepared in the same manner as Intermediate 5-3a.

(B) Preparation of Compound 20

Intermediate 5-3a (6.5 g, 9.79 mmol) 1- bromo-modify-benzo [b, d] furan (5e) (2.7 g, 10.8 mmol), Pd (t-Bu 3 P) 2 (0.1 g, 0.20 mmol) in And K ₃ PO ₄ (5.2 g, 24.5 mmol) dissolved in water were added to dioxane (150 mL), and the mixture was refluxed and stirred. After 10 hours, the reaction was terminated, the temperature was lowered to room temperature, filtered, and washed with water to remove the base. Recrystallization was performed using N-methyl-2-pyrrolidone to obtain Compound 20 (6.1 g, yield 78%, MS: [M + H] ⁺ = 796).

Manufacturing example  21: Preparation of Compound 21

(A) Preparation of intermediate 6-1a

Dibenzo [b, d] furan-3-ylboronic acid and dibenzo [b, d] furan-1-ylboronic acid and intermediate 2b instead of intermediate 3a were used in the same manner as in the preparation of intermediate 4-1a (107.6 g, yield 87%, MS: [M + H] < ⁺ > = 400).

(B) Preparation of intermediate 6-1b

Intermediate 6-1b was prepared in the same manner as Intermediate 4-1b except that Intermediate 4-1a was used instead of Intermediate 4-1a (63.3 g, yield 49%, MS: [M + H] ^{+ &} Gt ^; = 478).

(C) Preparation of intermediate 6-1c

Intermediate 6-1c was prepared in the same manner as Intermediate 3-3b except that Intermediate 6-1b was used instead of Intermediate 3-3a (58.0 g, yield 83% MS: [M + H] < ⁺ > = 526).

(D) Preparation of Compound 21

(15.2 g, yield 70%, MS: [M + H] +) was prepared in the same manner as Compound 1, except that Intermediate 6-1c and Intermediate 2b were used instead of Intermediate 1f and Intermediate 1b. H] < ⁺ > = 631).

Manufacturing example  22: Preparation of Compound 22

The compound (21) was obtained in the same manner as the compound 21, except that 4 - ([1,1'-biphenyl] -4-yl) -6-chloro-2-phenylpyridine 22 (10.0 g, yield 74%, MS: [M + H] < ⁺ > = 706).

Manufacturing example  23: Preparation of Compound 23

Compound 23 was prepared (10.3 g, yield 75%, MS: [M + H] ⁺ = 721) in the same manner as in the preparation of Compound 21, except that Intermediate 3a was used instead of Intermediate 2b.

Manufacturing example  24: Preparation of Compound 24

Compound 24 was prepared (9.9 g, yield 72%, MS: [M + H] < + > = 721) in the same manner as in the preparation of Compound 21, except that Intermediate 2c was used instead of Intermediate 2b.

Manufacturing example  25: Preparation of compound 25

Compound 24 was prepared (10.7 g, yield 80%, MS: [M + H] < ⁺ > = 707) in the same manner as in the preparation of Compound 21, except that Intermediate 2d was used instead of Intermediate 2b.

Manufacturing example  26: Preparation of compound 26

Compound 26 was prepared (7.7 g, yield 68%, MS: [M + H] + = 630) in the same manner as in the preparation of Compound 21, except that Intermediate 1a was used instead of Intermediate 2b.

Manufacturing example  27: Preparation of Compound 27

1) Preparation of intermediate 6-1e

(A) Preparation of intermediate 6-1d

Dibenzo [b, d] furan-3-ylboronic acid and (2-cyanophenyl) boronic acid and 2-chloro-4- (10.1 g, yield 75%, MS: [M + H] < ⁺ > = 369) in the same manner as in the preparation of intermediate 4-1a, except that azine was used.

(B) Preparation of intermediate 6-1e

Intermediate 6-1e was prepared in the same manner as Intermediate 3-3b except that Intermediate 6-1d was used instead of Intermediate 3-3a (9.5 g, yield 75% MS: [M + H] < ⁺ > = 461).

2) Preparation of compound 27

(11.3 g, yield 73%, MS: [M + H] < ⁺ > = 732) was prepared in the same manner as in the preparation of Compound 21, except that Intermediate 6-1e was used instead of Intermediate 6-1c. .

Manufacturing example  28: Synthesis of Compound 28

(7.1 g, yield 89%, MS: [M + H] < + > = 732) was prepared in the same manner as in the preparation of Compound 21, except that Intermediate 6-1e was used instead of Intermediate 2b.

Manufacturing example  29: Synthesis of Compound 29

(A) Preparation of intermediate 6-2a

Dibenzo [b, d] furan-3-ylboronic acid and dibenzo [b, d] furan-1-ylboronic acid and Intermediate 5c in place of Intermediate 3a were used in the same manner as Intermediate 4-1a (36.7 g, yield 83%, MS: [M + H] < ⁺ > = 476).

(B) Preparation of intermediate 6-2b

Intermediate 6-2b was prepared in the same manner as Intermediate 4-1b except that Intermediate 4-1a was used instead of Intermediate 4-1a (22.0 g, yield 52%, MS: [M + H] ⁺ = 554).

(C) Preparation of intermediate 6-2c

Intermediate 6-2c was prepared in the same manner as Intermediate 3-3b except that Intermediate 6-2b was used instead of Intermediate 3-3a (17.1 g, yield 72% MS: [M + H] < ⁺ > = 602).

(D) Preparation of compound 29

(13.7 g, yield 68%, MS: [M + H] < ⁺ > = 707) was prepared in the same manner as in the preparation of Compound 21, except that Intermediate 6-2c was used instead of Intermediate 6-1c. .

Manufacturing example  30: Synthesis of compound 30

(A) Preparation of intermediate 6-3a

Dibenzo [b, d] furan-3-ylboronic acid was used instead of dibenzo [b, d] furan-1-ylboronic acid and Intermediate 1a in place of Intermediate 3a. (52.8 g, yield 80%, MS: [M + H] < ⁺ > = 399).

(B) Preparation of intermediate 6-3b

Intermediate 6-3b was prepared in the same manner as Intermediate 4-1b except that Intermediate 6-3a was used instead of Intermediate 4-1a (31.8 g, yield 50%, MS: [M + H] ⁺ = 477).

(C) Preparation of intermediate 6-3c

Intermediate 6-3c was prepared in the same manner as Intermediate 3-3b except that Intermediate 3-3a was used instead of Intermediate 3-3a (22.8 g, yield 65% MS: [M + H] < ⁺ > = 525).

(D) Preparation of Compound 30

3-yl) -4-chloro-6-phenyl-1,3,5-triazine (6b) instead of Intermediate 6-3c and Intermediate 6b (9.9 g, yield 64%, MS: [M + H] < ⁺ > = 706) was prepared in the same manner as compound 21 was used.

Manufacturing example  31: Synthesis of Compound 31

(10.5 g, yield 69%, MS: [M + H] +) was prepared in the same manner as in the preparation of Compound 21, except that Intermediate 6-3c and Intermediate 1c were used instead of Intermediate 6-1c and Intermediate 2b. H] < ⁺ > = 705).

[ Experimental Example  One]

Example  One

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 50 Å to form a hole injection layer. N-phenylamino] biphenyl (NPB; HT-1), which is a material for transporting holes, was thermally vacuum deposited to a thickness of 250 Å to form a hole transport layer And an HT-2 compound was vacuum deposited on the HT-1 vapor deposition layer to a thickness of 50 Å to form an electron blocking layer. Compound 1 and phosphorescent dopant D1 previously prepared as a host were co-deposited on the HT-2 deposited film at a weight ratio of 16% to form a 400Å thick light emitting layer. An ET-1 material was vacuum deposited on the light-emitting layer to a thickness of 250 ANGSTROM and an ET-2 material was co-deposited with a 2% weight ratio Li to a thickness of 100 ANGSTROM to form an electron transport layer and an electron injection layer. Aluminum was deposited on the electron injecting layer to a thickness of 1000 to form a cathode.

In the above process, the deposition rate of the organic material was maintained at 0.4 to 0.7 Å / sec, the deposition rate of aluminum was maintained at 2 Å / sec, and the vacuum degree during deposition was maintained at 1 × 10 ^-7 to 5 × 10 ^-8 torr Thus, an organic light emitting device was fabricated.

Example  2 to Example  44

The organic light emitting devices of Examples 2 to 44 were fabricated in the same manner as in Example 1, except that Compound 1 was used as the phosphorescent host in the formation of the light emitting layer, as shown in Tables 1 and 2 below. In this case, when a mixture of two kinds of compounds is used as a host, parentheses mean weight ratio between host compounds, and H1 and D2 substances are as follows.

Comparative Example  1 to 13

The organic luminescent devices of Comparative Examples 1 to 13 were fabricated in the same manner as in Example 1, except that the following C1 to C8 were used instead of Compound 1 as a host in forming the light emitting layer, Respectively.

The voltage, efficiency, color coordinates, and lifetime were measured by applying current to the organic light emitting devices manufactured in Examples 1 to 44 and Comparative Examples 1 to 13, and the results are shown in Tables 1 to 3 below. T95 means the time required for the luminance to be reduced to 95% from the initial luminance.

Host
matter Dopant
matter Dopant
density(%) @ 10 mA / cm ² Color coordinates
(x, y) Life span (T95, h)
(@ 50 mA / cm ² ) Voltage
(V) efficiency
(cd / A) Example 1 Compound 1 D1 16 3.30 65 (0.465, 0.525) 54 Example 2 Compound 3 D1 12 3.25 63 (0.460, 0.533) 55 Example 3 Compound 4 D1 16 3.29 65 (0.466, 0.526) 46 Example 4 Compound 6 D1 12 3.20 66 (0.462, 0.530) 41 Example 5 Compound 7 D1 12 3.26 64 (0.461, 0.531) 40 Example 6 Compound 8 D2 10 3.40 56 (0.322, 0.611) 33 Example 7 Compound 9 D1 12 3.29 65 (0.459, 0.534) 38 Example 8 Compound 11 D1 12 3.30 63 (0.458, 0.532) 38 Example 9 Compound 12 D1 16 3.43 59 (0.466, 0.524) 35 Example 10 Compound 14 D1 12 3.21 62 (0.458, 0.531) 40 Example 11 Compound 15 D1 12 3.17 64 (0.458, 0.531) 34 Example 12 Compound 17 D1 12 3.23 67 (0.460, 0.534) 39 Example 13 Compound 19 D1 12 3.25 69 (0.462, 0.533) 39 Example 14 Compound 20 D1 12 3.21 65 (0.461, 0.532) 43 Example 15 Compound 21 D1 16 3.20 69 (0.466, 0.523) 40 Example 16 Compound 22 D1 12 3.23 63 (0.460, 0.531) 43 Example 17 Compound 23 D2 10 3.37 73 (0.322, 0.612) 42 Example 18 Compound 24 D1 12 3.22 70 (0.460, 0.532) 40 Example 19 Compound 27 D1 12 3.30 75 (0.464, 0.523) 42 Example 20 Compound 30 D1 12 3.25 70 (0.461, 0.531) 44 Example 21 Compound 31 D1 12 3.30 71 (0.462, 0.532) 41

Host material Dopant
matter Dopant
density
(%) @ 10 mA / cm ² Color coordinates
(x, y) life span
(T95, h)
(@ 50 mA / cm ² ) Voltage
(V) efficiency
(cd / A) Example 21 Compound 1: H1 (50:50) D2 15 3.60 66 (0.322, 0.612) 75 Example 22 Compound 2: H1 (50:50) D1 12 3.65 73 (0.460, 0.540) 121 Example 23 Compound 5: H1 (50:50) D1 12 3.64 72 (0.454, 0.540) 99 Example 24 Compound 7: H1 (50:50) D1 12 3.62 74 (0.460, 0.542) 102 Example 25 Compound 8: H1 (50:50) D1 12 3.63 75 (0.460, 0.541) 110 Example 26 Compound 9: H1 (50:50) D2 15 3.61 70 (0.322, 0.611) 76 Example 27 Compound 10: H1 (50:50) D1 12 3.51 67 (0.460, 0.540) 105 Example 28 Compound 11: H1 (50:50) D1 20 3.62 68 (0.451, 0.540) 109 Example 29 Compound 14: H1 (50:50) D1 12 3.55 71 (0.451, 0.530) 120 Example 30 Compound 15: H1 (50:50) D1 12 3.53 68 (0.451, 0.532) 132 Example 31 Compound 17: H1 (50:50) D1 12 3.59 75 (0.455, 0.542) 140 Example 32 Compound 18: H1 (50:50) D1 12 3.50 70 (0.451, 0.535) 135 Example 33 Compound 19: H1 (50:50) D1 12 3.51 69 (0.450, 0.538) 143 Example 34 Compound 20: H1 (50:50) D1 12 3.47 67 (0.450, 0.539) 139 Example 35 Compound 21: H1 (50:50) D1 20 3.43 76 (0.459, 0.533) 159 Example 36 Compound 22: H1 (50:50) D1 20 3.30 73 (0.450, 0.540) 167 Example 37 Compound 23: H1 (70:30) D1 12 3.42 69 (0.450, 0.542) 280 Example 38 Compound 24: H1 (50:50) D1 12 3.29 75 (0.450, 0.542) 165 Example 39 Compound 25: H1 (50:50) D1 12 3.30 80 (0.450, 0.541) 153 Example 40 Compound 26: H1 (50:50) D1 12 3.30 74 (0.460, 0.533) 161 Example 41 Compound 27: H1 (50:50) D1 12 3.54 79 (0.461, 0.532) 165 Example 42 Compound 28: H1 (50:50) D1 12 3.60 80 (0.460, 0.532) 166 Example 43 Compound 29: H1 (50:50) D1 12 3.33 72 (0.451, 0.540) 156

Host material Dopant
matter Dopant
density(%) @ 10 mA / cm ² Color coordinates
(x, y) life span
(T95, h)
(@ 50 mA / cm ² ) Voltage
(V) efficiency
(cd / A) Comparative Example 1 C1 D1 16 3.9 59 (0.466, 0.525) 32 Comparative Example 2 C2 D1 12 3.8 66 (0.462, 0.532) 33 Comparative Example 3 C4 D2 10 3.6 43 (0.322, 0.613) 29 Comparative Example 4 C5 D1 12 3.4 73 (0.457, 0.535) 31 Comparative Example 5 C6 D1 12 3.3 71 (0.460, 0.540) 36 Comparative Example 6 C7 D1 12 4.0 70 (0.463, 0.540) 49 Comparative Example 7 C8 D1 12 3.1 60 (0.460, 0.530) 40 Comparative Example 8 C2: H1 (50:50) D2 15 3.8 63 (0.322, 0.612) 70 Comparative Example 9 C3: H1 (50:50) D1 12 4.0 60 (0.460, 0.535) 74 Comparative Example 10 C4: H1 (50:50) D1 12 4.0 60 (0.460, 0.532) 61 Comparative Example 11 C6: H1 (50:50) D1 12 4.2 70 (0.460, 0.540) 81 Comparative Example 12 C7: H1 (50:50) D1 12 4.4 65 (0.460, 0.531) 88 Comparative Example 13 C8: H1 (50:50) D1 12 3.6 68 (0.450, 0.540) 91

As shown in Tables 1 to 3, in the case of the organic light emitting device manufactured by using the compound according to the present invention as a host of the light emitting layer, superior performance in terms of driving voltage, current efficiency and lifetime As shown in FIG. Particularly, when the compound of the present invention was used together with the H1 compound (Examples 21 to 44), it was confirmed that the driving voltage and lifetime were remarkably improved.

In particular, it was confirmed that the organic light emitting device according to the embodiment is superior in terms of driving voltage as the voltage is reduced by about 8-16% as compared with the organic light emitting device according to Comparative Example 7 using the compound C8 which is a commonly used phosphorescent host material there was. Similarly, a lower driving voltage was exhibited as compared with the organic light emitting devices according to Comparative Examples 1 and 2, in which two hetero substituents were symmetrically located (C1 and C2). The organic light emitting devices according to Comparative Examples 4 and 5 using the compounds C5 and C6 in which only one substituent of two substituents was a hetero substituent showed the advantages of driving voltage and efficiency as compared with Comparative Examples 1 and 2, 6, 7, 9, 11, 14, 17, 22, and 24, the lifetime was increased from 105% to 132%. In addition, the organic light emitting devices according to Examples 21 to 44, which were used together with the H1 compound, showed a lifetime increase of at least 120% to 235% as compared with the organic light emitting devices according to Comparative Examples 8 to 13.

In addition, the organic light emitting devices according to Examples 6 and 11 showed at least an efficiency increase of at least 30% and a lifetime increase of more than 113% as compared with the organic light emitting device according to Comparative Example 4 using Compound C4 having only one hetero substituent. In addition, the organic light emitting devices according to Examples 25 and 31, when used in combination with the H1 compound, exhibited efficiencies of 13% and 25% and lifetimes of 80% and 126%, respectively, as compared with the organic light emitting device according to Comparative Example 13.

Comparing Examples 1, 4, 7, 10, 12 and 16, it can be seen that the voltage and lifetime difference is shown depending on the substitution position of the dibenzofurane of the compound of the above-mentioned Examples, and the lifetime is improved at a specific position I could confirm. This tendency was also confirmed in the compounds of Examples 10 to 20 as compared with Examples 1 to 9. Comparing Examples 15 to 20 and Examples 35 to 40, the voltage and efficiency characteristics differ depending on the substituent types of L ₁ -HAr ₁ or L ₂ -HAr ₂ in Chemical Formula 1, and the efficiency, voltage, lifetime I was able to look at excellent materials in terms of.

As described above, it was confirmed that the compounds of the present invention exhibit excellent characteristics in terms of driving voltage and lifetime according to the substituent position, the number of bonds and the type of substituent, as compared with the comparative compounds.

[ Experimental Example  2]

Example  45

The following hexanitrile hexaazatriphenylene (HAT) compound was thermally vacuum deposited on the ITO transparent electrode prepared in Example 1 to a thickness of 500 Å to form a hole injection layer. The HT-1 compound was thermally vacuum deposited on the hole injection layer to a thickness of 800 Å, and HT-3 compound was vacuum deposited thereon to a thickness of 500 Å to form a hole transport layer. Subsequently, Compound 2, which was previously prepared as a host, was co-deposited with phosphorescent dopant D3 at a weight ratio of H2 on the hole transport layer to form a 350Å thick light emitting layer. The ET-3 material and the LiQ (Lithium Quinolate) were vacuum-deposited on the hole blocking layer at a weight ratio of 1: 1 on the hole blocking layer to form a 250 Å electron barrier layer. To form a transport layer. 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.

Example  46 to 66

The organic light emitting devices of Examples 46 to 66 were fabricated in the same manner as in Example 45, except that Compound 2 was used as a host in forming the light emitting layer, as shown in Tables 4 and 5 below. 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.

Comparative Example  14 to 19

The organic light emitting devices of Comparative Examples 14 to 19 were fabricated using the same method as in Example 45, except that the compound shown in Table 5 was used instead of Compound 1 as a host in forming the light emitting layer. The compounds shown in Table 5 below are the same as those used in Experimental Example 1.

The current, voltage, efficiency and lifetime of the organic light-emitting device fabricated in Examples 45 to 66 and Comparative Examples 14 to 19 were measured. The results are shown in Tables 4 and 5. T95 means the time required for the luminance to be reduced to 95% from the initial luminance.

Host material @ 10 mA / cm ² Color coordinates
(x, y) life span
(T95, h)
(@ 20 mA / cm ² ) Voltage
(V) efficiency
(cd / A) Example 45 Compound 2: H2 (50: 50) 4.4 64 (0.33, 0.61) 59 Example 46 Compound 3: H2 (50: 50) 4.3 66 (0.33, 0.61) 57 Example 47 Compound 5: H2 (50:50) 4.3 65 (0.34, 0.62) 51 Example 48 Compound 6: H2 (50:50) 4.4 64 (0.33, 0.60) 46 Example 49 Compound 9: H2 (50: 50) 4.5 65 (0.34, 0.60) 59 Example 50 Compound 11: H2 (50:50) 4.4 63 (0.35, 0.61) 56 Example 51 Compound 12: H2 (50:50) 4.5 66 (0.35, 0.61) 50 Example 52 Compound 13: H2 (50:50) 4.5 64 (0.35, 0.62) 54 Example 53 Compound 15: H2 (50:50) 4.3 55 (0.35, 0.62) 63 Example 54 Compound 16: H2 (50:50) 4.4 59 (0.36, 0.61) 61 Example 55 Compound 18: H2 (50: 50) 4.3 57 (0.35, 0.60) 64 Example 56 Compound 20: H2 (50:50) 4.4 58 (0.33, 0.62) 65 Example 57 Compound 21: H2 (50:50) 4.0 60 (0.34, 0.61) 83 Example 58 Compound 21: H2 (60:40) 4.1 61 (0.34, 0.61) 96 Example 59 Compound 22: H2 (50:50) 4.2 60 (0.35, 0.60) 71 Example 60 Compound 23: H2 (50:50) 4.07 57 (0.34, 0.61) 77 Example 61 Compound 23: H2 (60:40) 4.23 60 (0.34, 0.61) 107 Example 62 Compound 23: H2 (70:30) 4.3 62 (0.34, 0.61) 133 Example 63 Compound 24: H2 (50:50) 4.2 59 (0.33, 0.61) 80 Example 64 Compound 25: H2 (50:50) 4.1 57 (0.34, 0.62) 77 Example 65 Compound 26: H2 (50:50) 4.2 58 (0.33, 0.61) 79 Example 66 Compound 28: H2 (50:50) 4.3 57 (0.34, 0.60) 67

Host material @ 10 mA / cm ² Color coordinates
(x, y) life span
(T95, h,
@ 20 mA / cm ² ) Voltage
(V) efficiency
(cd / A) Comparative Example 14 C1: H2 (70:30) 4.9 56 (0.35, 0.63) 55 Comparative Example 15 C3: H2 (50:50) 4.6 65 (0.34, 0.62) 32 Comparative Example 16 C4: H2 (50:50) 4.6 49 (0.35, 0.62) 35 Comparative Example 17 C6: H2 (50:50) 4.4 61 (0.34, 0.63) 30 Comparative Example 18 C7: H2 (50: 50) 4.7 65 (0.34, 0.63) 45 Comparative Example 19 C8: H2 (50:50) 4.2 55 (0.35, 0.61) 55

As can be seen from Tables 4 and 5, when the compound of the present invention is used as a light emitting layer material, as compared with the case of using a comparative material, similar to Experimental Example 1, Can be seen.

Compared with the compounds of Examples 45 to 52, the compounds of Examples 53 to 57, 60, and 63 to 65 showed an efficiency, voltage, and lifetime difference depending on the substitution position of dibenzofurane, It can be confirmed that the efficiency is improved by about 120% when it is located at the fourth position of dibenzofurane. In addition, it was confirmed that the driving voltage and lifetime were improved when the substituent was located at position 1.

Also, similar to Experimental Example 1, Comparative Example 16 in which only one substituent was present in dibenzofurane than the Examples in Tables 4 and 5 has a high driving voltage and low lifetime. It is interpreted that the characteristics of the organic light emitting device are poor due to the inadequate balance in the process of injecting holes and electrons.

[ Experimental Example  3]

Example  67

The glass substrate coated with ITO (indium tin oxide) thin film with a thickness of 1,000 Å was immersed in distilled water containing detergent and washed with ultrasonic waves. In this case, Fischer Co. was used as a detergent, and distilled water filtered by a filter of Millipore Co. was used as distilled water. The ITO was washed for 30 minutes and then washed twice with distilled water and ultrasonically cleaned for 10 minutes. After the distilled water was washed, it was ultrasonically washed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner. Further, the substrate was cleaned using oxygen plasma for 5 minutes, and then the substrate was transported by a vacuum evaporator.

On this ITO transparent electrode, hexanitrile hexaazatriphenylene (HAT) of the following chemical formula was thermally vacuum deposited to a thickness of 500 Å to form a hole injection layer. N-phenylamino] biphenyl (HT-1) (400 Å), which is a material for transporting holes, was vacuum-deposited on the hole injection layer to form a hole transport layer . Subsequently, the following BH and BD were vacuum deposited on the hole transport layer at a weight ratio of 25: 1 at a thickness of 300 ANGSTROM to form a light emitting layer. The following compound ET-A was vacuum deposited on the light emitting layer to a thickness of 50 Å to form an electron transporting layer. Compound 1 and compound LiQ (Lithium Quinolate) prepared above were vacuum deposited on the electron transport layer at a weight ratio of 1: 1 to form an electron injection and transport layer having a thickness of 300 ANGSTROM. Lithium fluoride (LiF) and aluminum were deposited to a thickness of 2000 Å on the electron injecting and transporting layer sequentially to form a cathode.

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

Example  68 to 80

The organic light emitting devices of Examples 68 to 80 were fabricated in the same manner as in Example 67 except that Compound 1 was used in the form of an electron transport layer as shown in Table 6 below.

Comparative Example  20 to 23

Except that C1, C4, C11 and C12 were used in place of Compound 1 in the formation of the electron transport layer, respectively, as shown in Table 6 below, the organic light emitting devices of Comparative Examples 28 to 32 Respectively. Compounds C1 and C4 are the same as those used in Experimental Example 1, and the compounds of C11 and C12 are as follows.

The currents were applied to the organic light emitting devices fabricated in Examples 67 to 80 and Comparative Examples 20 to 23 to measure voltage and efficiency. The results are shown in Table 6 below.

compound Voltage (V)
(@ 10 mA / cm ² ) Efficiency (cd / A)
(@ 10 mA / cm ² ) Color coordinates
(x, y) Example 67 Compound 1 3.86 7.18 (0.133, 0.133) Example 68 Compound 3 3.88 7.19 (0.133, 0.132) Example 69 Compound 7 3.76 7.20 (0.134, 0.133) Example 70 Compound 8 3.77 7.15 (0.133, 0.135) Example 71 Compound 11 4.10 7.23 (0.133, 0.134) Example 72 Compound 12 4.15 7.15 (0.134, 0.132) Example 73 Compound 16 3.70 7.17 (0.134, 0.134) Example 74 Compound 17 3.71 7.20 (0.134, 0.132) Example 75 Compound 19 3.70 6.87 (0.133, 0.132) Example 76 Compound 21 3.68 7.00 (0.133, 0.133) Example 77 Compound 22 3.67 7.10 (0.133, 0.133) Example 78 Compound 25 3.63 7.22 (0.134, 0.132) Example 79 Compound 26 3.65 7.00 (0.134, 0.133) Example 80 Compound 27 3.66 6.95 (0.134, 0.132) Comparative Example 20 C1 3.90 5.20 (0.134, 0.133) Comparative Example 21 C4 3.95 4.07 (0.132, 0.133) Comparative Example 22 C11 3.60 5.81 (0.133, 0.133) Comparative Example 23 C12 3.90 6.81 (0.134, 0.132)

As can be seen from the above Table 6, when the compound of the present invention was used as an electron transport layer material, it was confirmed that the compound of the present invention exhibited excellent properties in terms of high efficiency and stability as compared with the case of using the compounds of Comparative Examples 20 to 23.

[ Experimental Example  4]

HOMO levels and PL _max were measured for the compounds of the above-mentioned Production Examples as follows. For comparison, the C8 compound and the C9 compound were also measured in the same manner. The C8 compound was the same as that used in Experimental Example 1, and the C9 compound was as follows.

(1) HOMO level: Measured with an AC-3 instrument. AC-3 was a model AC-3 manufactured by Rinken Keiki Co., Ltd. The film to be measured on the ITO substrate used for manufacturing the organic light emitting device was vacuum evaporated to a thickness of 1000Å, and the film was irradiated with UV intensity of 10 nW The HOMO level was determined by measuring the quantum yield of photon generated by the photon.

(2) Measurement of PL _max value: Measured using a spectrofluorometer FP-8600 model manufactured by JASCO. Specifically, the material to be measured was vacuum-deposited on a bare glass to a thickness of 1000 Å to prepare a film, and the emitted wavelength was scanned by irradiating UV with a specific wavelength on the film. At this time, PL _max was determined as the position with the highest intensity in the obtained spectrum. Based on the obtained PL _max data, the on-set value of the data graph obtained by excitation was determined as the band gap (Bg) of the compound.

The results are shown in Table 7 below. The results are also shown graphically in Figures 3 to 5 for some of them.

HOMO (eV) Bg (eV) PL _max (nm) Compound 11 6.30 3.25 417 Compound 21 6.21 3.30 405 Compound 22 6.30 3.29 407 Compound 23 6.26 3.28 403 Compound 24 6.06 3.32 406 C8 5.62 2.95 479 C9 5.73 2.97 459

As shown in Table 7, the PL _max (nm) value indicates that the compounds of the present invention are at least 40 nm (nm) compared to the compounds C8 and C9, which are hosts of the bi-polar or N-type characteristics of the commonly used green host And emission at a short wavelength of up to 76 nm. Also, when energy levels were compared, it was confirmed that the compounds of the present invention had a relatively high HOMO level energy and the band gap was about 0.35 eV as compared with the compounds C8 and C9.

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 (19)

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

In Formula 1,
X is O,
One of R _1a to R _4a is L ₁ -HAr ₁ , the other is A ₁ ,
One of R _1b to R _4b is L ₂ -HAr ₂ , the other is A ₂ ,
Provided that R &_lt; _{1a &} L ₁ -HAr ₁ , and R _2b is L ₂ -HAr ₂ ; R _1a is L ₁ -HAr ₁ , and R _4b is L ₂ -HAr ₂ ; R _2a is L ₁ -HAr ₁ , and R _3b is L ₂ -HAr ₂ ; R _2a is L ₁ -HAr ₁ , and R _4b is L ₂ -HAr ₂ ; Or R < _{3a &} L ₁ -HAr ₁ , R _4b is L ₂ -HAr ₂ ,
L ₁ and L ₂ each independently represent a direct 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, and the substituted or unsubstituted carbazolylene is excluded ,
HAr ₁ and HAr ₂ are each independently selected from the group consisting of at least two or more of N,

X ₁ to X ₃ are each independently N or CR ₇ ,
A ₁ , A ₂ , R ₇ , R ₁₁ and R ₁₂ are each independently hydrogen; heavy hydrogen; halogen; Cyano; Amino; Substituted or unsubstituted C _1-6 alkyl; Substituted or unsubstituted C _1-6 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,
n1 is an integer of 0 to 3;
delete delete delete The method according to claim 1,
L ₁ and L ₂ are each independently selected from the group consisting of a direct bond,
compound:

6. The method of claim 5,
L ₁ and L ₂ are each independently selected from the group consisting of a direct bond,
compound:

The method according to claim 1,
L &_lt; ₁ > is a direct bond;
L ₂ is a direct bond; or
L ₁ and L ₂ are direct bonds,
compound.
The method according to claim 1,
HAr ₁ and HAr ₂ are each independently any one selected from the group consisting of:
compound:

In the above,
R ₇ , R ₁₁ and R ₁₂ are each independently hydrogen; heavy hydrogen; halogen; Cyano; Amino; Substituted or unsubstituted C _1-20 alkyl; Substituted or unsubstituted C _1-20 haloalkyl; Substituted or unsubstituted C _6-20 aryl; Or a substituted or unsubstituted C _2-20 heterocyclic group containing at least one heteroatom selected from the group consisting of N, O and S.
9. The method of claim 8,
HAr ₁ and HAr ₂ are each independently any one selected from the group consisting of:

In the above,
R ₁₁ and R ₁₂ are each independently hydrogen; heavy hydrogen; halogen; Cyano; Amino; Substituted or unsubstituted C _1-20 alkyl; Substituted or unsubstituted C _1-20 haloalkyl; Substituted or unsubstituted C _6-20 aryl; Or a substituted or unsubstituted C _2-20 heterocyclic group containing at least one heteroatom selected from the group consisting of N, O and S.
The method according to claim 1,
L ₁ -HAr ₁ and L ₂ -HAr ₂ are each independently any one selected from the group consisting of:
compound:

The method according to claim 1,
A ₁ and A ₂ each independently represent hydrogen; heavy hydrogen; halogen; Cyano; Amino; Substituted or unsubstituted C _1-20 alkyl; Substituted or unsubstituted C _1-20 haloalkyl; Or substituted or unsubstituted C _6-20 aryl,
compound.
12. The method of claim 11,
A < _{1 >} and A < ₂ &
compound.
The method according to claim 1,
Wherein said compound is any one of compounds represented by the following formulas (1-1) and (1-3) - (1-6)
compound:
[Formula 1-1]

[Formula 1-3]

[Formula 1-4]

[Formula 1-5]

[Chemical Formula 1-6]

In the above formulas 1-1 and 1-3 to 1-6,
X, L ₁ , L ₂ , HAr ₁ and HAr ₂ are as defined in claim ₁ .
The method according to claim 1,
Wherein said compound is any one selected from the group consisting of the following compounds:

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 of the organic material layers is formed by a method according to any one of claims 1 and 5 to 14 ≪ / RTI >
16. The method of claim 15,
The organic compound layer containing the compound is a light-
Organic light emitting device.
17. The method of claim 16,
Such compounds include, but are not limited to,
Organic light emitting device.
18. The method of claim 17,
Wherein the light emitting layer further comprises a dopant compound.
Organic light emitting device.
16. The method of claim 15,
The organic compound layer containing the compound may include an electron injection layer; An electron transport layer; Or a layer which simultaneously performs electron injection and electron transport,
Organic light emitting device.

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