KR20180131412A - Novel compound and organic light emitting device comprising the same - Google Patents

Abstract

The present invention provides a novel compound containing two heteroatom-containing condensed ring structures in a molecule and an organic light emitting device having the same. The present invention provides the organic light emitting device comprising: a first electrode; a second electrode facing the first electrode; and one or more organic material layers provided between the first electrode and the second electrode. At least one layer of the organic material layers includes the compound of a chemical formula 1.

Description

TECHNICAL FIELD [0001] The present invention relates to a novel compound and an organic light emitting device comprising the compound.

Cross-reference with related application (s)

This application claims priority from Korean Patent Application No. 10-2017-0067963, filed on May 31, 2017, 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. The organic material layer may have a multilayer structure composed of different materials in order to improve the efficiency and stability of the organic light emitting device. For example, the organic material layer may include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer. When a voltage is applied between 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 containing two heteroatom-containing condensed ring structures in a molecule and an organic light emitting device comprising the same.

The present invention provides compounds of formula 1:

[Chemical Formula 1]

In Formula 1,

L is a bond; Substituted or unsubstituted C _6-60 arylene; Or a substituted or unsubstituted C _2-60 heteroarylene containing at least one heteroatom selected from O, N, Si and S,

A and D are each independently any one of the functional groups represented by the following general formulas (2-1) to (2-6), provided that A and D are not any of functional groups represented by the following general formulas (2-1) to

[Formula 2-1]

[Formula 2-2]

[Formula 2-3]

[Chemical Formula 2-4]

[Chemical Formula 2-5]

[Chemical Formula 2-6]

In the above Formulas (2-1) to (2-6)

X ₅ and X ₆ are each independently selected from the group consisting of O, S and CR ₁ R ₂ ,

R ₁ and R ₂ are each independently a substituted or unsubstituted C _1-60 alkyl,

Z is - [(L ₁ ) _m -Y] _n , _wherein L ₁ is a bond; Substituted or unsubstituted C _6-60 arylene; Or a substituted or unsubstituted C _2-60 heteroarylene containing at least one heteroatom selected from O, N, Si and S,

Y is hydrogen; heavy hydrogen; halogen; Nitrile; Nitro; Amino; Substituted or unsubstituted C _1-6 alkyl; Substituted or unsubstituted C _3-60 cycloalkyl; Substituted or unsubstituted C _2-60 alkenyl; Substituted or unsubstituted C _6-60 aryl; Or a substituted or unsubstituted C _2-60 heterocyclic group containing at least one heteroatom selected from O, N, Si and S,

m and n are each an integer of 0 or 1;

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 the compound of Formula 1.

The compound of 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 of Formula 1 described above can be used as luminescent, electron transport, 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 의미한다. In the present specification,

Quot; means a bond connected to another substituent.

As used herein, the term " substituted or unsubstituted " A halogen group; A nitrile group; 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, the "substituent group to which two or more substituents are connected" may be a biphenyl group. That is, the biphenyl group may be an aryl group, and 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 is specifically exemplified by a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, And the like.

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, Pentyl, 3-methylbutyl, 2-ethylbutyl, 2-methylbutyl, 2-methylbutyl, N-heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, But are not limited to, 2-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, But are not limited to, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like.

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 heterocyclic group such as heterocycloalkyl or heteroaryl containing at least one heteroatom selected from O, N, Si and S as a hetero atom, and the number of carbon atoms is not particularly limited, 60 < / RTI > 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 quinazoline 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 group, 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.

On the other hand, the present invention provides a compound of formula 1:

[Chemical Formula 1]

In Formula 1,

L is a bond; Substituted or unsubstituted C _6-60 arylene; Or a substituted or unsubstituted C _2-60 heteroarylene containing at least one heteroatom selected from O, N, Si and S,

A and D are each independently any one of the functional groups represented by the following formulas (2-1) to (2-6), provided that when A and D are both functional groups represented by the following formulas (2-1) to Is the same functional group selected from the functional groups represented by the following general formulas (2-1) to (2-6)

[Formula 2-1]

[Formula 2-2]

[Formula 2-3]

[Chemical Formula 2-4]

[Chemical Formula 2-5]

[Chemical Formula 2-6]

In the above Formulas (2-1) to (2-6)

X ₅ and X ₆ are each independently selected from the group consisting of O, S and CR ₁ R ₂ ,

R ₁ and R ₂ are each independently a substituted or unsubstituted C _1-60 alkyl,

Z is - [(L ₁ ) _m -Y] _n , _wherein L ₁ is a bond; Substituted or unsubstituted C _6-60 arylene; Or a substituted or unsubstituted C _2-60 heteroarylene containing at least one heteroatom selected from O, N, Si and S,

Y is hydrogen; heavy hydrogen; halogen; Nitrile; Nitro; Amino; Substituted or unsubstituted C _1-6 alkyl; Substituted or unsubstituted C _3-60 cycloalkyl; Substituted or unsubstituted C _2-60 alkenyl; Substituted or unsubstituted C _6-60 aryl; Or a substituted or unsubstituted C _2-60 heterocyclic group containing at least one heteroatom selected from O, N, Si and S,

m and n are each an integer of 0 or 1;

As described above, the compound of Formula 1 according to the present invention includes a large condensed ring structure in which five aromatic or heteroaromatic rings are condensed to form a large conjugated system in a molecule. Accordingly, the carrier mobility of the layer containing the compound of Formula 1 in the organic light emitting device can be increased, and as a result, lifetime characteristics of the device can be improved.

A and D contained in the compound of formula (1) are each independently any one of the functional groups of the above formulas (2-1) to (2-6), provided that both A and D are the functional groups When A and D are any one of the same functional groups selected from the functional groups of the above formulas (2-1) to (2-6) (for example, both A and D are functional groups of formula (2-1) . Since condensation rings of A and D have different skeleton structures, an asymmetric structure is formed around L in this way. Accordingly, when the thin film is formed by vapor deposition, the amorphousness of the film is further strengthened as compared with the case of having a symmetrical structure, thereby reducing the barrier appearing at the interface with the surrounding layer, thereby lowering the driving voltage of the device.

Specifically, in Formula 1, L is a bond; Substituted or unsubstituted phenylene; Substituted or unsubstituted naphthalene-diyl; Substituted or unsubstituted carbazole-diyl; And substituted or unsubstituted dibenzofurandiyl. When L is substituted, C _1-20 alkyl; C _3-20 cycloalkyl; C _4-20 (cycloalkyl) alkyl; C _6-20 aryl; C _7-20 arylalkyl, and C _7-20 may be substituted one or more by one or more substituents selected from the group consisting of alkyl, aryl, more specifically from the group consisting of methyl, ethyl, propyl, t- butyl and phenyl Lt; RTI ID = 0.0 > 1 < / RTI > to 3 substituents.

A and D bonded to both sides of L are the condensed ring groups selected from the group consisting of the above-mentioned formulas (2-1) to (2-6), and the compound represented by the formula (1) has a different skeleton structure .

In the general formulas (2-1) to (2-6), X ₅ and X ₆ are each independently a chalcogen atom selected from the group consisting of O and S, or CR ₁ R ₂ .

For example, when at least one of X ₅ and X ₆ is a chalcogen atom selected from the group consisting of O and S, in the functional group of the general formulas (2-1) to (2-6), at least one of A and D is a chalcogen And has a condensed ring structure including an aromatic heterocycle containing an atom. In this case, since the chalcogen atom contained in the condensed ring structure has a high electronegativity with respect to the carbon atom and at the same time has a non-covalent electron pair, it is advantageous in charge transport in the compound of the formula (1), and therefore,

Further, in the case X ₅ or X ₆ is a CR ₁ R _2, R ₁ and R ₂ are, each independently, a substituted or unsubstituted C _1-60 alkyl, more specifically, a C _1- substituted or unsubstituted the _20-alkyl, still more specifically a substituted or unsubstituted methyl, or ethyl. When R ₁ and R ₂ are substituted, C _1-20 alkyl; C _3-20 cycloalkyl; C _4-20 (cycloalkyl) alkyl; C _6-20 aryl; C _7-20 arylalkyl, and C _7-20 may be substituted one or more by one or more substituents selected from the group consisting of alkyl, aryl, more specifically from the group consisting of methyl, ethyl, propyl, t- butyl and phenyl Lt; RTI ID = 0.0 > 1 < / RTI > to 3 substituents.

In the above formulas (2-1) to (2-6), Z is - [(L ₁ ) _m -Y] _{n wherein} L ₁ , Y, m and n are as defined above. More specifically, in the above Z, L &_lt; ₁ > is a bond; Substituted or unsubstituted C _6-60 arylene, such as substituted or unsubstituted phenylene, substituted or unsubstituted naphthalene- _diyl ; Or substituted or unsubstituted C _2-60 heteroatoms containing one or more heteroatoms of O, N, Si and S, such as substituted or unsubstituted carbazole-diyl, substituted or unsubstituted dibenzofurandiyl, Lt; / RTI > L &_lt; ₁ > is a bond; Or a substituted or unsubstituted C _6-20 arylene. When L ₁ is substituted, C _1-20 alkyl; C _3-20 cycloalkyl; C _4-20 (cycloalkyl) alkyl; C _6-20 aryl; C _7-20 arylalkyl, and C _7-20 may be substituted one or more by one or more substituents selected from the group consisting of alkyl, aryl, more specifically from the group consisting of methyl, ethyl, propyl, t- butyl and phenyl Lt; RTI ID = 0.0 > 1 < / RTI > to 3 substituents.

In the above Z, Y is specifically hydrogen; Substituted or unsubstituted C _1-20 alkyl; Substituted or unsubstituted C _3-20 cycloalkyl; Substituted or unsubstituted C _6-20 aryl; Or a substituted or unsubstituted C _2-20 heterocyclic group containing at least one heteroatom selected from O, N, Si and S. Specific examples thereof include, but are not limited to, the following functional groups:

More specifically, in the Z, Y is hydrogen; Substituted or unsubstituted C _1-20 alkyl; Substituted or unsubstituted C _3-20 cycloalkyl; Or substituted or unsubstituted C _6-20 aryl, more particularly hydrogen; C _1-4 alkyl such as methyl and ethyl; C _3-6 cycloalkyl such as cyclohexyl; And phenyl. ≪ / RTI >

When Y is substituted, C _1-20 alkyl; C _3-20 cycloalkyl; C _4-20 (cycloalkyl) alkyl; C _6-20 aryl; _C7-20 arylalkyl; And C _7-20 alkylaryl, and more specifically may be substituted with at least one substituent selected from the group consisting of methyl, ethyl, propyl, t-butyl and phenyl 1 to 3 substituents.

The compound of formula (1) can further improve the effect of the present invention by optimizing the functional group according to the structure.

In formula (1), when L is a bond, A and D are each independently any one of the functional groups represented by the general formulas (2-1) to (2-6) 2-1 to be in the functional groups of 2-6, except when any one of, and also the formula 2-1 to 2-6, X ₅ and X ₆ is any one of O, S, CR ₁ R ₂ and optionally replaced with another And more specifically X ₅ and X ₆ are the same O and Z is - [(L ₁ ) _m -Y] _n , wherein m and n are each 0.

When L is substituted or unsubstituted phenylene, the compound of formula (1) may be any one of the functional groups represented by formulas (2-1) to (2-6) And D is any one of the functional groups represented by the following general formulas (2-1) to (2-6), Z is - [(L ₁ ) _m -Y] _n , Wherein L &_lt; ₁ > is a bond; Or substituted or unsubstituted C _6-60 arylene, Y is hydrogen; Substituted or unsubstituted C _1-6 alkyl; Substituted or unsubstituted C _3-60 cycloalkyl; Or substituted or unsubstituted C _6-60 aryl, m and n are each an integer of 0 or 1, and more specifically, a compound wherein X ₅ and X ₆ are the same or are CR ₁ R ₂ . Wherein R ₁ and R ₂ are as defined above.

The compound of Chemical Formula 1 is a naphthalene-diyl group wherein L is a substituted or unsubstituted naphthalene-diyl group in Formula 1, and A and D are each independently any one of the functional groups represented by Chemical Formulas 2-1 to 2-6, In the above formulas (2-1) to (2-6), Z is - [(L ₁ ) _m -Y] _n ( ₁ ), except that both A and D are any of functional groups represented by the following formulas , Wherein L &_lt; ₁ > is a bond; Or substituted or unsubstituted C _6-60 arylene, Y is hydrogen; heavy hydrogen; Substituted or unsubstituted C _1-6 alkyl; Substituted or unsubstituted C _3-60 cycloalkyl; Or substituted or unsubstituted C _6-60 aryl, and m and n are each an integer of 0 or 1, and more specifically, X ₅ and X ₆ may be the same O.

In the above formula (1), L is a substituted or unsubstituted carbazole group, more specifically a phenyl substituted carbazole group, A and D are each independently a group represented by the formula (2) 1 to 2 to 6, provided that in the general formulas (2-1) to (2-6), Z is any one of functional groups represented by Z - [(L ₁ ) _m -Y] _n , _wherein m and n are each 0, and more specifically X ₅ and X ₆ can be the same S.

The specific contents of the functional groups in the above structures are as described above.

Representative examples of the compound of Formula 1 include, but are not limited to,

The compound of formula (1) has two heteroatom-containing condensed ring structures in the molecule, thereby enhancing the amorphousness of the film during the formation of the thin film through deposition, thereby reducing the barrier appearing at the interface with the surrounding layer . Therefore, the organic light emitting device using the same can have a high efficiency, a low driving voltage, a high brightness, and a long life, as compared with an organic light emitting device employing a compound having the same substitution group of an amino group.

The compound (I) of the above formula (1) can be prepared, for example, by a Suzuki reaction through coupling between a functional group AL-containing halide (II) and an organic boron compound (III) containing a functional group D . 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, L and D are as defined above,

X is a halogen or halogen-containing group such as I, Br, Cl, or -Otf (triflates)

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

Although the halide (II) includes the functional group of AL- and the organoboron compound (III) includes the functional group of D in the reaction scheme 1, the organic boron compound (III) contains the functional group of AL- , And the halide (II) may contain a functional group of D.

Specifically, the compound (I) of the formula (1) can be prepared by subjecting the organic boron compound (III) to a Suzuki coupling reaction with the halide (II) in the presence of a base and a palladium catalyst.

As the above-mentioned palladium catalyst, tetrakis- (triphenylphosphine) palladium (Pd (PPH ₃ ) ₄ ), palladium acetate, etc. may be used as the above-mentioned base, and sodium carbonate, potassium carbonate, sodium hydroxide or potassium hydroxide may be used as the base . The reaction may also be carried out in one or more organic solvents such as tetrahydrofuran (THF), N, N-dimethylformamide (DMF), dimethylsulfoxide (DMSO) or toluene.

The Suzuki coupling reaction of the above reaction scheme 1 may be carried out at a temperature in the range of 80 ° C to 120 ° C.

On the other hand, the organoboron compound (III) can be produced directly or commercially. Can be prepared in the same manner as in the method of Reaction Scheme 2 below. The following Reaction Scheme 2 is only one example for illustrating the present invention, but the present invention is not limited thereto.

[Reaction Scheme 2]

In the above Reaction Scheme 2, NBS is n-bromosuccinimide, DMF is dimethylformamide, NMP is N-methylpyrrolidone, THF is tetrahydrofuran, AN is acetonitrile, and KOAc is potassium acetate.

The compound of Formula 1 may be prepared by appropriately substituting the starting material according to the structure of the compound to be prepared with reference to Reaction Schemes 1 and 2.

The present invention also provides an organic light emitting device comprising the compound of 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 the compound of 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, or an electron injecting layer, as an organic material layer, and also between the hole transporting layer and the light emitting layer, The electron blocking layer and the hole blocking layer, respectively. However, the structure of the organic light emitting device is not limited thereto and may include a smaller number of organic layers.

The organic material layer may include a hole injecting layer, a hole transporting layer, or a layer simultaneously injecting and transporting holes, and the hole injecting layer, the hole transporting layer, ≪ / RTI >

In addition, the organic layer may include a light emitting layer, and the light emitting layer includes the compound of Formula 1.

The organic material layer may include an electron transporting layer or an electron injecting layer, and the electron transporting layer or the electron injecting layer includes the compound of the above formula (1).

In addition, the electron transporting layer, the electron injecting layer, or the layer which simultaneously injects electrons and transports electrons includes the compound of the above formula (1). In particular, the compound of formula (I) according to the present invention is excellent in thermal stability and has a deep HOMO level of 6.0 eV or more, a high triple energy (ET), and a hole stability. When the compound of Chemical Formula 1 is used for an organic material layer capable of electron injection and electron transport at the same time, an n-type dopant used in the art can be mixed and used.

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

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

Fig. 1 shows an example of an organic light-emitting device comprising a substrate 1, an anode 2, a light-emitting layer 3 and a cathode 4. Fig. In this structure, the compound of 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 of 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, and more specifically, it may be included in the light emitting layer.

The organic light emitting device according to an embodiment of the present invention may include a substrate, an anode, a hole transporting layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transporting layer, an electron injecting layer and a cathode. The compound of Formula 1 may be included in the light emitting 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 of 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 at least one of a hole injection layer, a hole transporting layer, a light emitting layer and an electron transporting layer thereon, and then depositing a material usable as a cathode on the organic material layer. In addition, when the organic material layer further includes an electron blocking layer and a hole blocking layer between the hole transporting layer and the light emitting layer, and between the light emitting layer and the electron transporting layer, forming the layers may be further included. In addition to such a method, an organic light emitting device can be formed by sequentially depositing a cathode material, an organic material layer, and a cathode material on a substrate.

In addition, the compound of Formula 1 may be formed into an organic layer by a solution coating method as well as a vacuum deposition method in the production of an organic light emitting device. Here, the solution coating method refers to spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating and the like, but is not limited thereto.

In addition to such a method, an organic light emitting device can be manufactured by sequentially depositing an organic material layer and a cathode material 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 to the organic material layer. Specific examples of the positive electrode material include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO: Al or SNO _2: a combination of a metal and an oxide such as Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDOT), polypyrrole and polyaniline.

The negative electrode material is preferably a material having a small work function to facilitate electron injection into the organic material layer. Specific examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or alloys thereof; Layer structure materials such as LiF / Al or LiO ₂ / Al, but are not limited thereto.

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

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

The light emitting material is preferably a material capable of emitting light in the visible light region by transporting and receiving holes and electrons from the hole transporting layer and the electron transporting layer, respectively, and having good quantum efficiency for fluorescence or phosphorescence. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq ₃ ); Carbazole-based compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; Compounds of the benzoxazole, benzothiazole and benzimidazole series; Polymers of poly (p-phenylenevinylene) (PPV) series; Spiro compounds; Polyfluorene, rubrene, and the like, but are not limited thereto.

The light emitting layer may include a host material and a dopant material. The host material is a condensed aromatic ring derivative or a heterocyclic compound. Specific examples of the condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds and fluoranthene compounds. Examples of 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 dopant content may range from 1% to 99% relative to the host amount of the light emitting layer.

The electron transporting material 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. Is suitable. Specific examples include an Al complex of 8-hydroxyquinoline; Complexes containing Alq ₃ ; Organic radical compounds; Hydroxyflavone-metal complexes, and the like, but are not limited thereto. The 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.

In addition, when the organic bladder element further includes at least one of an electron blocking layer and a hole blocking layer between the hole transporting layer and the light emitting layer, and between the light emitting layer and the electron transporting layer, the electron blocking layer prevents the electrons from reaching the anode Layer can be formed under the same conditions as those of the electron injection layer. The electron blocking layer is made of a material having a function of transporting holes and capable of transporting electrons with a remarkably small capacity to transport electrons. By blocking electrons while transporting holes, the probability of recombination of electrons and holes can be improved.

The hole blocking layer is a layer that prevents injected holes from entering the electron transporting layer through the light emitting layer to improve the lifetime and efficiency of the device. The hole blocking layer may include a nitrogen-containing heterocyclic derivative such as an oxadiazole derivative or a triazole derivative , Phenanthroline derivatives, BCP or aluminum complexes, but are not limited thereto. Specifically, the hole blocking layer may include a nitrogen-containing heterocyclic derivative as disclosed in Korean Patent Registration No. 10-1052973 and Korean Patent Registration No. 10-1317495.

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 of 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 of Formula 1 and the organic light emitting device comprising the compound of 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.

In the following Synthesis Examples and Examples, the room temperature means 23 ± 5 ° C.

Synthesis Example 1: Synthesis of Compound A

Step 1) Synthesis of Compound A-1

A three-necked flask was charged with 1,2-difluoro-3,6-diiodobenzene (70.0 g, 191.3 mmol), 2-methoxyphenylboronic acid (69.8 g, 459.2 mmol), 2M Na ₂ CO ₃ aqueous solution 383ml, 765.3mmol), 1,2- dimethoxyethane (DME) (383ml), toluene _{(383ml), Pd (PPh 3} ) into a ₄ (22.1g, 19.1mmol) was stirred 8 hours under reflux conditions in an argon atmosphere Respectively. When the reaction was completed, the reaction solution was cooled to room temperature, and the resulting reaction solution was transferred to a separatory funnel, and water (500 ml) was added thereto and extracted with CH ₂ Cl ₂ . The extract was dried with MgSO ₄ , filtered and concentrated. The resulting sample was purified by silica gel column chromatography to obtain 40.6 g of a white solid (yield 65%, MS [M + H] ⁺ = 326).

Step 2) Synthesis of Compound A-2

Compound A-1 (40.0 g, 122.6 mmol), NBS (21.8 g, 122.6 mmol) and dimethylformamide (DMF) (1200 ml) were placed in a two-necked flask and reacted under stirring at room temperature for 8 hours. After completion of the reaction, the resulting reaction solution was transferred to a separatory funnel, added with water (1000 ml) and extracted with ethyl acetate (AcOEt). The resulting sample was purified by silica gel column chromatography to give 40.7 g of a white solid (yield: 82%, MS [M + H] ⁺ = 405).

Step 3) Synthesis of Compound A-3

Compound A-2 (40.0 g, 98.7 mmol), 1 M BBr ₃ CH ₂ Cl ₂ solution (237 ml, 236.9 mmol) and CH ₂ Cl ₂ (592 mmol) were added to a _two- necked flask, Lt; / RTI > After stirring at room temperature for another 4 hours, it was neutralized with saturated aqueous NaHCO ₃ solution. The resulting reaction solution was transferred to a separatory funnel and extracted with CH ₂ Cl ₂ and the extract was purified by silica gel column chromatography to obtain 31.6 g of a white solid (Yield: 85%, MS [M + H] ⁺ = 377 )

Step 4) Synthesis of Compound A-4

(30.0 g, 79.5 mmol), K ₂ CO ₃ (24.2 g, 175.0 mmol) and N-methylpyrrolidone (NMP) (330 mL) were placed in a two-necked flask and the mixture was stirred at 150 ° C. for 8 hours And reacted with stirring. After completion of the reaction, the reaction solution was cooled to room temperature, and the resulting reaction solution was transferred to a separatory funnel, and water (500 ml) was added thereto and extracted with AcOEt. The resulting extract was purified by silica gel column chromatography to obtain 23.9 g of a white solid (yield: 89%, MS [M + H] ⁺ = 337).

Step 5) Synthesis of Compound A

Compound A-4 (20.0 g, 59.3 mmol) and THF (593 ml) were placed in a three-necked flask and cooled to -78 ° C. n-BuLi (1.6 M n-hexane solution, 41 ml, 65.2 mmol) was added dropwise thereto, and the mixture was stirred at -78 캜 for 20 minutes. Triisopropyl borate (33.47 g, 178.0 mmol) was added and the mixture was stirred at -78 ° C for 1 hour and then at room temperature for 4 hours. Then, 1N HCl (200 ml) was added and the mixture was stirred at room temperature for 1 hour. The resulting reaction solution was concentrated and transferred to a separatory funnel. Water (200 ml) was added thereto and extracted with CH ₂ Cl ₂ . The extract was dried over MgSO ₄ , filtered, concentrated and recrystallized from toluene-hexane to obtain 10.8 g of Compound A (yield: 60%, MS [M + H] ⁺ = 302).

Synthetic example  2: Synthesis of compound B

Except that 1,2-difluoro-3,6-diiodobenzene was changed to 1,3-dibromo-4,6-difluorobenzene in Synthesis Example 1, Compound B was synthesized using the same method.

Synthetic example  3: Synthesis of Compound C

Except that 1,2-difluoro-3,6-diiodobenzene was changed to 1,4-dibromo-2,5-difluorobenzene in Synthesis Example 1, Compound C was synthesized using the same method.

Synthetic example  4: Synthesis of Compound D

Except that 1,2-difluoro-3,6-diiodobenzene was changed to 1,2-dibromo-3,6-difluorobenzene in Synthesis Example 1, Compound D was synthesized using the same method.

Synthesis Example 5: Synthesis of Compound E

Step 1) Synthesis of Compound E-1

Compound A-1 (35.0 g, 107.3 mmol), NBS (38.2 g, 214.5 mmol) and DMF (1000 ml) were placed in a two-necked flask and reacted under stirring at room temperature for 8 hours under argon atmosphere. After completion of the reaction, the reaction solution was transferred to a separatory funnel, and water (1000 ml) was added thereto and extracted with AcOEt. The resulting sample was purified by silica gel column chromatography to give 40.5 g of a white solid (yield: 78%, MS [M + H] ⁺ = 484).

Step 2) Synthesis of Compound E-2

A solution of the compound E-1 (40.0 g, 82.6 mmol), 1 M BBr ₃ CH ₂ Cl ₂ solution (198 ml, 198.3 mmol) and CH ₂ Cl ₂ (496 mmol) was added to a _two- necked flask, Lt; / RTI > After stirring at room temperature for another 4 hours, it was neutralized with saturated aqueous NaHCO ₃ solution. The resulting reaction solution was transferred to a separatory funnel and extracted with CH ₂ Cl _{2. The} extract was purified by silica gel column chromatography to give 30.1 g of a white solid (Yield: 80%, MS [M + H] ⁺ = 456 )

Step 3) Synthesis of Compound E-3

Compound E-2 (30.0 g, 65.8 mmol), K ₂ CO ₃ (20.0 g, 144.7 mmol) and NMP (270 ml) were placed in a two-necked flask and reacted with stirring at 150 ° C. for 8 hours under argon atmosphere. After completion of the reaction, the reaction mixture was cooled to room temperature, and the resulting reaction solution was transferred to a separatory funnel. Water (400 ml) was added thereto and extracted with AcOEt. The resulting extract was purified by silica gel column chromatography to obtain 21.1 g of a white solid (yield: 77%, MS [M + H] ⁺ = 416).

Step 4) Synthesis of Compound E-4

A solution of compound E-3 (20.0 g, 48.1 mmol), phenylboronic acid (5.9 g, 48.1 mmol), 2M Na ₂ CO ₃ aqueous solution (72 ml, 144.2 mmol), DME (95 ml), toluene _{Pd (PPh 3) 4 (5.6g} , 4.8mmol) and the mixture, stirred for 8 hours under reflux conditions in an argon atmosphere and allowed to react. After completion of the reaction, the reaction mixture was cooled to room temperature, and the resulting reaction solution was transferred to a separatory funnel. Water (200 ml) was added thereto and extracted with CH ₂ Cl ₂ . The extract was dried with MgSO ₄ , filtered and concentrated. The resulting sample was purified by silica gel column chromatography to obtain 15.1 g of a white solid (yield: 76%, ms [M + H] + = 413).

Step 5) Synthesis of Compound E

Compound E-4 (15.0 g, 36.3 mmol) and THF (363 ml) were placed in a three-necked flask and cooled to -78 ° C. n-BuLi (1.6M n-hexane solution, 25.0 ml, 39.9 mmol) was added dropwise and the mixture was stirred at -78 캜 for 20 minutes. Triisopropyl borate (20.5 g, 108.9 mmol) was added and the mixture was stirred at -78 ° C for 1 hour and then at room temperature for 4 hours. Then 1N HCl (120 ml) was added and the mixture was stirred at room temperature for 1 hour. The resulting reaction solution was concentrated, transferred to a separatory funnel, added with water (120 ml) and extracted with CH ₂ Cl ₂ . The extract was dried over MgSO ₄ , filtered, concentrated and recrystallized from toluene-hexane to obtain 9.6 g of Compound E (Yield: 70%, MS [M + H] ⁺ = 378).

Synthetic example  6: Synthesis of Compound F

Compound F was synthesized in the same manner as in Synthesis Example 5, except that Compound B-1 was used instead of Compound A-1 in Synthesis Example 5.

Synthetic example  7: Synthesis of Compound G

Compound G was synthesized in the same manner as in Synthesis Example 5, except that Compound C-1 was used instead of Compound A-1 in Synthesis Example 5.

Synthetic example  8: Synthesis of compound H

Compound H was synthesized in the same manner as in Synthesis Example 5, except that Compound D-1 was used instead of Compound A-1 in Synthesis Example 5.

Production Example 1: Synthesis of Compound 1

Step 1) Synthesis of Compound 1-1

A solution of Compound G (8.0 g, 21.2 mmol), 3-bromoiodobenzene (6.0 g, 21.2 mmol), 2M Na ₂ CO ₃ aqueous solution (32 ml, 63.5 mmol) and DME 42ml), toluene _{(42ml), Pd (PPh 3} ) into a ₄ (2.1g, 2.1mmol) was reacted with stirring for 8 hours under reflux conditions in an argon atmosphere. After the reaction was completed, the reaction solution was cooled to room temperature, and the resulting reaction solution was transferred to a separatory funnel. Water (42 ml) was added thereto and extracted with CH ₂ Cl ₂ . The extract was dried over MgSO ₄ , filtered and concentrated. The resulting sample was purified by silica gel column chromatography to give 15.1 g of a white solid (Yield: 70%, MS [M + H] ⁺ = 489 ).

Step 2) Synthesis of Compound 1

(7.0 g, 14.3 mmol) prepared in the above Step 1, the compound H (6.0 g, 15.7 mmol) prepared in Synthesis Example 8, 2 M Na ₂ CO ₃ aqueous solution (21 ml, 42.9 mmol ), DME (30ml), toluene _{(30ml), Pd (PPh 3} ) into a ₄ (1.7g, 1.4mmol), stirred and reacted in eight hours under reflux conditions in an argon atmosphere. After the reaction was completed, the reaction solution was cooled to room temperature, and the resulting reaction solution was transferred to a separatory funnel. Water (60 ml) was added thereto and extracted with CH ₂ Cl ₂ . The resulting extract was dried with MgSO ₄ , filtered and concentrated. The resulting sample was purified by silica gel column chromatography, and then 5.3 g of Compound 1 was obtained through sublimation purification (Yield: 50%, MS [M + H] < ⁺ > = 743).

Production Example 2: Synthesis of Compound 2

Step 1) Synthesis of Compound 2-1

Three-necked flask was charged with the compound prepared in the above Synthesis Example 2 B (6.5g, 21.5mmol), 4- bromo Moai Goto benzene (6.1g, 21.5mmol), 2M Na 2 CO 3 aqueous solution (32ml, 64.6mmol), DME ( 45ml), toluene _{(45ml), Pd (PPh 3} ) into a ₄ (2.5g, 2.2mmol), was reacted under an argon atmosphere was stirred under reflux for 8 hours conditions. After the reaction was completed, the reaction solution was transferred to a separatory funnel, and water (90 ml) was added thereto, followed by extraction with CH ₂ Cl ₂ . The extract was dried over MgSO ₄ , filtered and concentrated. The resulting sample was purified by silica gel column chromatography to give 6.0 g of a white solid (Yield: 68%, MS [M + H] ⁺ = 489 ).

Step 2) Synthesis of Compound 2

(6.0 g, 14.5 mmol), Compound E (6.0 g, 16.0 mmol) prepared in Synthesis Example 5, 2 M Na ₂ CO ₃ aqueous solution (22 ml, 43.6 mmol) prepared in Step 1, , DME (30 ml), toluene (30 ml) and Pd (PPh ₃ ) ₄ (1.7 g, 1.4 mmol) were placed and reacted under reflux conditions under argon atmosphere for 8 hours. After the reaction was completed, the reaction solution was cooled to room temperature, and the resulting reaction solution was transferred to a separatory funnel. Water (60 ml) was added thereto and extracted with CH ₂ Cl ₂ . The resulting extract was dried with MgSO ₄ , filtered and concentrated. The resulting sample was purified by silica gel column chromatography, and 4.6 g of compound 2 was obtained through sublimation purification (yield: 48%, MS [M + H] < ⁺ > = 667).

Production Example 3: Synthesis of Compound 3

Step 1) Synthesis of Compound 3-1

Compound D (7.0 g, 23.2 mmol), 2,7-dibromonaphthalene (6.6 g, 23.2 mmol), 2M Na ₂ CO ₃ aqueous solution (35 ml, 69.5 mmol), DME (45ml), toluene _{(45ml), Pd (PPh 3} ) into a ₄ (2.7g, 2.3mmol) was reacted with stirring for 8 hours under reflux conditions in an argon atmosphere. After the reaction was completed, the reaction solution was cooled to room temperature, and the resulting reaction solution was transferred to a separatory funnel, and water (90 ml) was added thereto and extracted with CH ₂ Cl ₂ . The extract was dried over MgSO ₄ , filtered and concentrated. The resulting sample was purified by silica gel column chromatography to give 7.5 g of a white solid (Yield: 70%, MS [M + H] ⁺ = 463 ).

Step 2) Synthesis of Compound 3

Compound 3-1 (7.0 g, 15.1 mmol), Compound A (5.0 g, 16.6 mmol) and 2M Na ₂ CO ₃ aqueous solution (23 ml, 45.3 mmol) prepared in Synthesis Example 1 were added to a three- , DME (30ml), toluene _{(30ml), Pd (PPh 3} ) into a ₄ (1.7g, 1.5mmol), it stirred and reacted in eight hours under reflux conditions in an argon atmosphere. After the reaction was completed, the reaction solution was cooled to room temperature, and the resulting reaction solution was transferred to a separatory funnel. Water (60 ml) was added thereto and extracted with CH ₂ Cl ₂ . The resulting extract was dried with MgSO ₄ , filtered and concentrated. The resulting sample was purified by silica gel column chromatography, and 4.9 g of compound 3 was obtained through sublimation purification (yield: 51%, MS [M + H] < ⁺ > = 641).

Production Example 4: Synthesis of Compound 4

Step 1) Synthesis of Compound 4

Compound A (5.0 g, 16.6 mmol) prepared in Synthesis Example 1, Compound C-4 (6.1 g, 18.2 mmol) prepared in Synthesis Example 3, 2 M Na ₂ CO ₃ aqueous solution (25 ml, 49.7 mmol ), DME (33ml), toluene _{(32ml), Pd (PPh 3} ) into a ₄ (1.9g, 1.7mmol), stirred and reacted in eight hours under reflux conditions in an argon atmosphere. When the reaction was completed, the reaction solution was cooled to room temperature, and the resulting reaction solution was transferred to a separatory funnel, and water (66 ml) was added thereto, followed by extraction with CH ₂ Cl ₂ . The resulting extract was dried with MgSO ₄ , filtered and concentrated. The resulting sample was purified by silica gel column chromatography, and 4.7 g of Compound 4 was obtained through sublimation purification (yield: 47%, MS [M + H] < ⁺ > = 515).

Production Example 5: Synthesis of Compound 5

Step 1) Synthesis of Compound 5-1

Three-necked compound I (5.0g, 15.0mmol) in a flask, 3,6-dibromo-9-phenyl -9H- carbazole (6.0g, 15.0mmol), 2M Na 2 CO 3 aqueous solution (22ml, 44.9mmol), put DME (30ml), toluene _{(30ml), Pd (PPh 3} ) 4 (1.7g, 1.5mmol) was reacted with stirring for 8 hours under reflux conditions in an argon atmosphere. After the reaction was completed, the reaction solution was cooled to room temperature, and the resulting reaction solution was transferred to a separatory funnel. Water (60 ml) was added thereto and extracted with CH ₂ Cl ₂ . The extract was dried over MgSO ₄ , filtered and concentrated. The resulting sample was purified by silica gel column chromatography to give 6.4 g of a white solid (Yield: 70%, MS [M + H] ⁺ = 611 ).

Step 2) Synthesis of Compound 5

To the three-necked flask was added the compound 5-1 (6.2 g, 10.2 mmol), the compound J (3.7 g, 11.2 mmol), 2M Na ₂ CO ₃ aqueous solution (15 ml, 30.5 mmol), DME toluene _{(20ml), Pd (PPh 3} ) into a ₄ (1.2g, 1.0mmol), stirred and reacted in eight hours under reflux conditions in an argon atmosphere. After the reaction was completed, the reaction solution was cooled to room temperature, and the resulting reaction solution was transferred to a separatory funnel. Water (40 ml) was added thereto and extracted with CH ₂ Cl ₂ . The resulting extract was dried with MgSO ₄ , filtered and concentrated. The resulting sample was purified by silica gel column chromatography, and 3.9 g of compound 5 was obtained through sublimation purification (yield: 47%, MS [M + H] < ⁺ > = 820).

Production Example 6: Synthesis of Compound 6

Step 1) Synthesis of Compound 6-1

(7.2 g, 18.5 mmol), 3-bromoiodobenzene (5.2 g, 18.5 mmol), 2M Na ₂ CO ₃ aqueous solution (28 ml, 55.5 mmol) and DME 37ml), toluene _{(37ml), Pd (PPh 3} ) into a ₄ (2.1g, 1.9mmol) was reacted with stirring for 8 hours under reflux conditions in an argon atmosphere. After the reaction was completed, the reaction solution was cooled to room temperature, and the resulting reaction solution was transferred to a separatory funnel. Water (80 ml) was added thereto and extracted with CH ₂ Cl ₂ . The extract was dried over MgSO ₄ , filtered and concentrated. The resulting sample was purified by silica gel column chromatography to give 6.0 g of a white solid (Yield: 66%, MS [M + H] ⁺ = 489 ).

Step 2) Synthesis of Compound 6

To the three-necked flask was added the compound 6-1 (6.0 g, 12.3 mmol), Compound K (4.8 g, 13.5 mmol), 2M Na ₂ CO ₃ aqueous solution (18 ml, 36.8 mmol), DME Toluene (25 ml) and Pd (PPh ₃ ) ₄ (1.4 g, 1.2 mmol) were added thereto and reacted under reflux conditions under argon atmosphere for 8 hours. After the reaction was completed, the reaction solution was cooled to room temperature, and the resulting reaction solution was transferred to a separatory funnel. Water (50 ml) was added thereto and extracted with CH ₂ Cl ₂ . The resulting extract was dried with MgSO ₄ , filtered and concentrated. The resulting sample was purified by silica gel column chromatography, and 4.2 g of compound 6 was obtained via sublimation purification (yield: 48%, MS [M + H] < ⁺ > = 719).

<Device Manufacturing Example>

Example 1

A glass substrate coated with ITO (Indium Tin Oxide) with a thickness of 1,400 Å was immersed in distilled water dissolved in detergent and washed with ultrasonic waves. As a detergent, Fischer Co.'s Decon? CON705 was used as the distilled water, and distilled water secondarily filtered with a 0.22 μm sterilizing filter manufactured by Millipore Co. was used as the distilled water. The ITO was washed for 30 minutes and then washed twice with distilled water and ultrasonically cleaned for 10 minutes. After the distilled water was washed, it was ultrasonically washed with a solvent of isopropyl alcohol, acetone and methanol for 10 minutes, dried, and then transported to a plasma cleaner. The substrate was cleaned using oxygen plasma for 5 minutes, and then the substrate was transported by a vacuum evaporator.

On this ITO transparent electrode, a mixture of 95 wt% of HT-A and 5 wt% of P-DOPANT was thermally vacuum deposited to a thickness of 100 Å, and then HT-A was deposited to a thickness of 1150 Å to form a hole transport layer.

The following HT-B was vacuum deposited on the HTL to a thickness of 450 ANGSTROM to form an electron blocking layer.

Subsequently, a mixture of 95% by weight of the following compound 1 and 5% by weight of dopant GD was vacuum deposited on the electron blocking layer to a thickness of 400 Å to form a light emitting layer.

Further, on the light emitting layer, ET-A shown below was vacuum-deposited to a thickness of 50 ANGSTROM to form a hole blocking layer.

Next, ET-B and Liq were mixed at a weight ratio of 2: 1 on the hole blocking layer to form an electron transport layer by thermal vacuum deposition to a thickness of 250 ANGSTROM, followed by mixing LiF and magnesium at a weight ratio of 1: 1 And vacuum evaporated at a thickness of 30 ANGSTROM to form an electron injection layer.

Magnesium and silver were mixed on the electron injecting layer at a weight ratio of 1: 4 and then vapor deposited at a thickness of 160 Å to form a cathode. Thus, an organic light emitting device was fabricated.

Example  2 to 6, and Comparative Example  1 to 4

The organic light emitting devices of Examples 2 to 6 and Comparative Examples 1 to 4 were fabricated in the same manner as in Example 1, except that the host materials were changed to the materials listed in Table 1 below.

 The voltage, efficiency and lifetime (T95) were measured by applying current to the fabricated organic light emitting device, and the results are shown in Table 1 below.

At this time, the voltage and the efficiency were measured by applying a current density of 10 mA / cm ² , and the lifetime (T 95) means a time until the initial luminance decreased to 95% at a current density of 20 mA / cm ² .

Host material @ 10ma / cm &lt; ² &gt; @ 20ma / cm ² Voltage (V) Efficiency (cd / A) Life (T95, hr) Example 1 Compound 1 4.46 59.55 120 Example 2 Compound 2 4.43 54.15 130 Example 3 Compound 3 4.48 56.43 110 Example 4 Compound 4 4.38 55.25 140 Example 5 Compound 5 4.46 57.39 130 Example 6 Compound 6 4.50 53.73 120 Comparative Example 1 GH-A 4.56 42.11 80 Comparative Example 2 GH-B 4.67 38.19 70 Comparative Example 3 GH-C 4.65 40.15 30 Comparative Example 4 GH-D 4.78 41.55 60

As a result of the test, the organic electroluminescent devices of Examples 1 to 6 containing the compounds (Preparation 1 to 6) of Production Examples 1 to 6 containing two different hetero atom-containing condensed ring structures in the molecule as the light emitting layer Or an increase in efficiency as compared with the organic electroluminescent devices of Comparative Examples 1 to 4 including a compound having heteroatom-containing condensed rings of the same skeletal structure on both sides, and exhibited remarkably improved life characteristics Respectively.

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 (11)

A compound of formula
[Chemical Formula 1]

In Formula 1,
L is a bond; Substituted or unsubstituted C _6-60 arylene; Or a substituted or unsubstituted C _2-60 heteroarylene containing at least one heteroatom selected from O, N, Si and S,
A and D are each independently any one of the functional groups represented by the following general formulas (2-1) to (2-6), provided that A and D are not any of functional groups represented by the following general formulas (2-1) to
[Formula 2-1]

[Formula 2-2]

[Formula 2-3]

[Chemical Formula 2-4]

[Chemical Formula 2-5]

[Chemical Formula 2-6]

In the above Formulas (2-1) to (2-6)
X ₅ and X ₆ are each independently selected from the group consisting of O, S and CR ₁ R ₂ ,
R ₁ and R ₂ are each independently a substituted or unsubstituted C _1-60 alkyl,
Z is - [(L ₁ ) _m -Y] _n , _wherein L ₁ is a bond; Substituted or unsubstituted C _6-60 arylene; Or a substituted or unsubstituted C _2-60 heteroarylene containing at least one heteroatom selected from O, N, Si and S,
Y is hydrogen; heavy hydrogen; halogen; Nitrile; Nitro; Amino; Substituted or unsubstituted C _1-6 alkyl; Substituted or unsubstituted C _3-60 cycloalkyl; Substituted or unsubstituted C _2-60 alkenyl; Substituted or unsubstituted C _6-60 aryl; Or a substituted or unsubstituted C _2-60 heterocyclic group containing at least one heteroatom selected from O, N, Si and S,
m and n are each an integer of 0 or 1;
The method according to claim 1,
L is a bond; Substituted or unsubstituted phenylene; Substituted or unsubstituted naphthalene-diyl; Substituted or unsubstituted carbazole-diyl; And substituted or unsubstituted dibenzofurandiyl.
The method according to claim 1,
Z is - [(L ₁ ) _m -Y] _n , L ₁ is a bond; Or substituted or unsubstituted C _6-20 arylene,
Y is hydrogen; Substituted or unsubstituted C _1-20 alkyl; Substituted or unsubstituted C _3-20 cycloalkyl; Or substituted or unsubstituted C _6-20 aryl, and m and n are each an integer of 0 or 1.
The method according to claim 1,
Wherein L is a bond,
A and D are each independently any one of the functional groups of the above-mentioned general formulas (2-1) to (2-6), except that A and D are both functional groups of the following general formulas (2-1) to
In Formula 2-1 to 2-6, X ₅ and X ₆ is O, S, CR _1, and R being optionally replaced with either the same, and each of the ₂ Z is _{- [(L 1) m -Y} ] n provided that, m And n is 0 each.
The method according to claim 1,
Wherein L is substituted or unsubstituted phenylene,
A and D are each independently any one of the functional groups of the above-mentioned general formulas (2-1) to (2-6), provided that A and D are both functional groups of the following general formulas (2-1) to
In the above Formulas 2-1 to 2-6, Z is - [(L ₁ ) _m -Y] _n , _wherein L ₁ is a bond; Or substituted or unsubstituted C _6-60 arylene,
Y is hydrogen; Substituted or unsubstituted C _1-6 alkyl; Substituted or unsubstituted C _3-60 cycloalkyl; Or substituted or unsubstituted C _6-60 aryl,
m and n are each an integer of 0 or 1.
6. The method of claim 5,
In the general formulas (2-1) to (2-6), X ₅ and X ₆ are each O or CR ₁ R ₂ .
The method according to claim 1,
L is a substituted or unsubstituted naphthalene-diyl group,
A and D are each independently any one of the functional groups of the above-mentioned general formulas (2-1) to (2-6), except that A and D are both functional groups of the following general formulas (2-1) to
In the above Formulas 2-1 to 2-6, Z is - [(L ₁ ) _m -Y] _n , _wherein L ₁ is a bond; Or substituted or unsubstituted C _6-60 arylene,
Y is hydrogen; heavy hydrogen; Substituted or unsubstituted C _1-6 alkyl; Substituted or unsubstituted C _3-60 cycloalkyl; Or substituted or unsubstituted C _6-60 aryl,
m and n are each an integer of 0 or 1.
The method according to claim 1,
L is a substituted or unsubstituted carbazole group,
A and D are each independently any one of the functional groups of the above-mentioned general formulas (2-1) to (2-6), except that A and D are both functional groups of the following general formulas (2-1) to
In the above formulas 2-1 to 2-6, Z is - [(L ₁ ) _m -Y] _n , _wherein m and n are each 0.
The method according to claim 1,
Lt; / RTI &gt; 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 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,
Wherein the organic compound layer containing the compound is a light emitting layer.

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