KR20150068282A - Novel organic electroluminescent compound, organic electroluminescent device including the same and electric apparatus - Google Patents

Abstract

The present invention provides an organic electroluminescent compound represented by Chemical formula 1 and an organic electroluminescent device including the same. In Chemical formula 1, X, Y, Z, Ar1, Ar2, Ar3, R1, L1 and L2 are same as defined in the specification. The organic electroluminescent compound can be applied as a green phosphorescent host material, a hole injection layer material, a hole transport layer material, an electron injection layer material, or an electron transport layer material to an organic electroluminescent device. In this case, the organic electroluminescent compound can increase light emission efficiency and durability of the organic electroluminescent device.

Description

TECHNICAL FIELD [0001] The present invention relates to a novel organic electroluminescent compound, an organic electroluminescent device including the organic electroluminescent compound, and an electronic device including the same. BACKGROUND ART [0002]

A novel organic electroluminescent compound, an organic electroluminescent device including the same, and an electronic apparatus.

The electroluminescence phenomenon in organic semiconductors was first found in anthracene crystals by Pope, Kallmann, Magnate in 1963 [M. Pope, H. P. Kallmamm and P. Magnae, J. Chem. Phys. 38, 2042 (1963)], and then in 1965 by W. Helfrich [W. Helfrich and W. G. Schneider, Phys. Rev. Lett. 14, 229 (1965)].

In 1987, Eastman Kodak Company first developed an organic EL device using an aromatic diamine and an aluminum complex having low molecular weight as a light emitting layer forming material [Appl. Phys. Lett. 51, 913, 1987). For organic electroluminescent devices, C. W. Tang et al. In 1987 first reported practical devices with practical performance (Applied Physics Letters, 51, (12), 913-915, 1987).

This document describes a structure in which a thin film (hole transporting layer) of a diamine derivative and a thin film (electron transporting light emitting layer) of Alq3 (tris (8-hydroxyquinolate) aluminum) are stacked as an organic layer.

In the organic electroluminescent device, when holes are injected from the anode and electrons are injected from the cathode, holes and electrons move toward the counter electrode and recombine to form excitons having high energy. At this time, The exciton formed is a device that generates light having a specific wavelength while moving to a ground state. Such light emission can be divided into fluorescence using excitons in singlet state and phosphorescence using excitons in triplet state. Recently, it has been known that not only fluorescence but also phosphorescence can be used as luminescence of organic electroluminescent devices (DFO'Brien et al., Applied Physics Letters, 74 (3), 442-444, 1999; MA Baldo et al., Applied Physics letters, 75 (1), 4-6, 1999).

The organic electroluminescent device generally has a lamination structure of an anode / an organic light emitting layer / a cathode and includes an anode / a hole injecting layer / a hole transporting layer / a light emitting layer / an electron transporting layer / an electron injecting layer / a cathode or an anode / a hole injecting layer / Electron blocking layer, hole blocking layer / electron transporting layer / electron injecting layer / cathode, and the like.

In organic electroluminescent devices, the most problematic is the lifetime and efficiency. As the display becomes larger, such efficiency and lifetime problems must be solved. Organic light emitting compounds having excellent hole injecting and transporting ability in an organic electroluminescent device improve the light emission lifetime of an electric device by lowering the driving voltage of the device and increasing the luminous efficiency and brightness.

Korean Patent Publication No. 2000-0048009, US Patent No. 5,061,569, US Patent No. 5,374,489 and US Patent No. 5,554,450 disclose aromatic amine compounds that can be used in the hole transport layer.

As a compound that can be used for the hole injecting layer and / or the hole transporting layer, Copper Phthalocyanine compound (US Patent No. 4,356,429), Oligothiophene (US Patent No. 5,540,999) No. 5,616,427 discloses a quinacridone based material, and Korean Patent No. 377,321 discloses a hexaazatriphenylene based derivative.

Korean Patent Publication No. 2011-0111095, Korean Patent Publication No. 2011-0041727, and Korean Patent Publication No. 2013-0106255 disclose carbazole-based derivatives.

However, development of a stable and efficient organic luminescent compound for an organic electroluminescent device has not yet been sufficiently achieved, and development of a new material has been continuously required. In particular, development of a phosphorescent material and a hole transport layer is urgently required.

SUMMARY OF THE INVENTION The present invention has been made in order to solve the problems of the prior art as described above, and it is an object of the present invention to provide an organic electroluminescent device, which is a phosphorescent material such as a phosphorescent green host material, a hole injecting layer material, a hole transporting layer material, And it is an object of the present invention to provide an organic light emitting compound capable of lowering a driving voltage when applied to an organic electroluminescent device and improving luminous efficiency, brightness, thermal stability, color purity, and device life.

It is another object of the present invention to provide an organic electroluminescent device using the organic electroluminescent compound.

Another embodiment of the present invention provides an electronic apparatus to which the organic electroluminescent device is applied.

In one embodiment of the present invention, there is provided an organic electroluminescent compound represented by the following general formula (1).

≪ Formula 1 >

In this formula,

R1 is hydrogen, halogen, _{nitrile, CF 3, -Si (CH 3} ) 3, linear or branched C1 ~ C10 linear or branched alkyl, C1 ~ C10 alkoxy, phenyl or pyridinyl group, or; or

Halogen, _{nitrile, CF 3, -Si (CH 3} ) 3, C1 ~ C10 straight or branched chain alkyl, C1 ~ C10 linear or branched alkoxy, phenyl, _{pyridinyl, -N (C 6 H 5)} 2 and Substituted or unsubstituted < RTI ID = 0.0 >

Phenyl, pyridinyl, triazinyl, naphthyl, 9,9-dimethylfluorenyl, dibenzofuranyl, dibenzothiophene, carbazole, or -N (C ₆ H ₅ ) ₂ group;

L1 is a simple bond; Phenyl or -N (C ₆ H ₅ ) ₂ , Phenyl; Or a divalent moiety of pyridine;

L2 is a simple bond; Or phenyl substituted or unsubstituted with a phenyl group, naphthalene substituted or unsubstituted with a phenyl group, biphenyl substituted or unsubstituted with a phenyl group, 9,9-dimethylfluorene substituted or unsubstituted with a phenyl group, or substituted or unsubstituted phenyl group Is a divalent moiety of a substituted - (9,9-dimethylfluorene) - (phenyl);

X is a carbon atom or a nitrogen atom;

Y is an aromatic ring; Or a C1-C10 linear or branched alkyl group substituted or unsubstituted with at least one member selected from the group consisting of C1-C10 alkyl groups and phenyl groups,

The aromatic ring is deuterium; halogen; Nitrile; CF _3; -Si (CH _{3) 3;} C1 to C10 straight or branched chain alkyl; Straight or branched chain alkoxy of C1 to C10; -N (C ₆ H ₅ ) ₂ or a substituted or unsubstituted Phenyl; Pyridinyl; And -N (C ₆ H ₅₎ in one or more selected from the group consisting of a _{2-substituted} or unsubstituted

Phenyl, pyridinyl, triazinyl, naphthyl, 9,9-dimethylfluorenyl, dibenzofuranyl, dibenzothiophene, carbazole or -N (C ₆ H ₅ ) ₂ ;

Z is deuterium, halogen, _{nitrile, CF 3, -Si (CH 3} ) 3, a C1 ~ C10 linear or branched alkyl, linear or branched C1 ~ C10 alkoxy, pyridinyl and 9,9-dimethyl fluorenyl flow carbonyl Or a substituted or unsubstituted < RTI ID = 0.0 >

이며,Straight or branched chain alkyl of C1 to C10, phenyl, pyridinyl, triazinyl, naphthyl, 9,9-dimethylfluorenyl, dibenzofuranyl, dibenzothiophene, carbazole or

Lt;

R2 and R3 are each independently selected from the group consisting of C1 to C10 linear or branched alkyl, C1 to C10 linear or branched alkoxy, Phenyl, pyridinyl, and -N (C ₆ H ₅ ) ₂ , or a substituted or unsubstituted

A straight or branched chain alkyl of C1 to C10, phenyl, pyridinyl, triazinyl, naphthyl, 9,9-dimethylfluorenyl, dibenzofuranyl, dibenzothiophene, or carbazole group,

Wherein L2 and R2 or R3 may be connected to form a 5-membered ring or a 6-membered ring which is substituted or unsubstituted with at least one member selected from the group consisting of C1-C10 straight-chain or branched-chain alkyl and phenyl groups,

The R2 or R3 may be connected to form a 5-membered or 6-membered ring, which is substituted or unsubstituted with at least one member selected from the group consisting of C1-C10 straight-chain or branched-chain alkyl and phenyl, An oxygen atom, a nitrogen atom and a sulfur atom;

Wherein at least one carbon atom, nitrogen atom, oxygen atom or sulfur atom of Y and N adjacent to Y are substituted or unsubstituted with at least one group selected from the group consisting of C1 to C10 linear or branched alkyl and phenyl groups, A 5-membered ring or a 6-membered ring to be fused to a ring containing X;

Ar1, Ar2 and Ar3 are each independently selected from deuterium, halogen, _{nitrile, CF 3, -Si (CH 3} ) 3, straight-chain or branched-chain alkyl of C1 ~ C10, linear or branched C1 ~ C10 alkoxy; -N (C ₆ H ₅ ) ₂ or a substituted or unsubstituted Phenyl; Pyridinyl, carbazole, and -N (C ₆ H ₅ ) ₂ , or a substituted or unsubstituted

Phenyl, pyridinyl, triazinyl, naphthyl, 9,9-dimethylfluorenyl, dibenzofuranyl, dibenzothiophene, carbazole or -N (C ₆ H ₅ ) ₂ group;

Wherein L2 or Z and Ar3 may be connected to form a 5-membered ring or a 6-membered ring substituted or unsubstituted with at least one member selected from the group consisting of C1-C10 straight-chain or branched-chain alkyl and phenyl groups, The ring or six-membered ring may contain one or more hetero atoms selected from an oxygen atom, a nitrogen atom and a sulfur atom;

Y and Ar1 may be connected to form a 5-membered ring or a 6-membered ring which is substituted or unsubstituted with at least one member selected from the group consisting of C1-C10 straight-chain or branched-chain alkyl and phenyl groups, May contain one or more hetero atoms selected from an oxygen atom, a nitrogen atom and a sulfur atom.

According to another embodiment of the present invention, there is provided an organic electroluminescence device in which a single layer or a plurality of organic thin film layers including at least a light emitting layer is sandwiched between a cathode and an anode,

Wherein at least one of the organic thin film layers contains the organic electroluminescent compound singly or in combination of two or more.

In another embodiment of the present invention, there is provided an electronic device including the organic electroluminescent device.

The organic light emitting compound may be applied to an organic light emitting device as a phosphorescent material such as a phosphorescent green host material, a hole injection layer material, a hole transport layer material, an electron injection layer material, or an electron transport layer material. And improves luminous efficiency, luminance, thermal stability, color purity, and device life.

In addition, the organic electroluminescent device manufactured using the organic electroluminescent compound has high efficiency and long life.

Hereinafter, embodiments of the present invention will be described in detail. However, the present invention is not limited thereto, and the present invention is only defined by the scope of the following claims.

In one embodiment of the present invention, there is provided an organic electroluminescent compound represented by the following general formula (1).

≪ Formula 1 >

In this formula,

R1 is hydrogen, halogen, _{nitrile, CF 3, -Si (CH 3} ) 3, linear or branched C1 ~ C10 linear or branched alkyl, C1 ~ C10 alkoxy, phenyl or pyridinyl group, or; or

Halogen, _{nitrile, CF 3, -Si (CH 3} ) 3, C1 ~ C10 straight or branched chain alkyl, C1 ~ C10 linear or branched alkoxy, phenyl, _{pyridinyl, -N (C 6 H 5)} 2 and Substituted or unsubstituted < RTI ID = 0.0 >

Phenyl, pyridinyl, triazinyl, naphthyl, 9,9-dimethylfluorenyl, dibenzofuranyl, dibenzothiophene, carbazole, or -N (C ₆ H ₅ ) ₂ group;

L1 is a simple bond; Phenyl or -N (C ₆ H ₅ ) ₂ , Phenyl; Or a divalent moiety of pyridine;

L2 is a simple bond; Or phenyl substituted or unsubstituted with a phenyl group, naphthalene substituted or unsubstituted with a phenyl group, biphenyl substituted or unsubstituted with a phenyl group, 9,9-dimethylfluorene substituted or unsubstituted with a phenyl group, or substituted or unsubstituted phenyl group Is a divalent moiety of a substituted - (9,9-dimethylfluorene) - (phenyl);

X is a carbon atom or a nitrogen atom;

Y is an aromatic ring; Or a C1-C10 linear or branched alkyl group substituted or unsubstituted with at least one member selected from the group consisting of C1-C10 alkyl groups and phenyl groups,

The aromatic ring is deuterium; halogen; Nitrile; CF _3; -Si (CH _{3) 3;} C1 to C10 straight or branched chain alkyl; Straight or branched chain alkoxy of C1 to C10; -N (C ₆ H ₅ ) ₂ or a substituted or unsubstituted Phenyl; Pyridinyl; And -N (C ₆ H ₅₎ in one or more selected from the group consisting of a _{2-substituted} or unsubstituted

Phenyl, pyridinyl, triazinyl, naphthyl, 9,9-dimethylfluorenyl, dibenzofuranyl, dibenzothiophene, carbazole or -N (C ₆ H ₅ ) ₂ ;

Z is deuterium, halogen, _{nitrile, CF 3, -Si (CH 3} ) 3, a C1 ~ C10 linear or branched alkyl, linear or branched C1 ~ C10 alkoxy, pyridinyl and 9,9-dimethyl fluorenyl flow carbonyl Or a substituted or unsubstituted < RTI ID = 0.0 >

이며,Straight or branched chain alkyl of C1 to C10, phenyl, pyridinyl, triazinyl, naphthyl, 9,9-dimethylfluorenyl, dibenzofuranyl, dibenzothiophene, carbazole or

Lt;

R2 and R3 are each independently selected from the group consisting of C1 to C10 linear or branched alkyl, C1 to C10 linear or branched alkoxy, Phenyl, pyridinyl, and -N (C ₆ H ₅ ) ₂ , or a substituted or unsubstituted

A straight or branched chain alkyl of C1 to C10, phenyl, pyridinyl, triazinyl, naphthyl, 9,9-dimethylfluorenyl, dibenzofuranyl, dibenzothiophene, or carbazole group,

Wherein L2 and R2 or R3 may be connected to form a 5-membered ring or a 6-membered ring which is substituted or unsubstituted with at least one member selected from the group consisting of C1-C10 straight-chain or branched-chain alkyl and phenyl groups,

The R2 or R3 may be connected to form a 5-membered or 6-membered ring, which is substituted or unsubstituted with at least one member selected from the group consisting of C1-C10 straight-chain or branched-chain alkyl and phenyl, An oxygen atom, a nitrogen atom and a sulfur atom;

Wherein at least one carbon atom, nitrogen atom, oxygen atom or sulfur atom of Y and N adjacent to Y are substituted or unsubstituted with at least one group selected from the group consisting of C1 to C10 linear or branched alkyl and phenyl groups, A 5-membered ring or a 6-membered ring to be fused to a ring containing X;

Ar1, Ar2 and Ar3 are each independently selected from deuterium, halogen, _{nitrile, CF 3, -Si (CH 3} ) 3, straight-chain or branched-chain alkyl of C1 ~ C10, linear or branched C1 ~ C10 alkoxy; -N (C ₆ H ₅ ) ₂ or a substituted or unsubstituted Phenyl; Pyridinyl, carbazole, and -N (C ₆ H ₅ ) ₂ , or a substituted or unsubstituted

Phenyl, pyridinyl, triazinyl, naphthyl, 9,9-dimethylfluorenyl, dibenzofuranyl, dibenzothiophene, carbazole or -N (C ₆ H ₅ ) ₂ group;

Wherein L2 or Z and Ar3 may be connected to form a 5-membered ring or a 6-membered ring substituted or unsubstituted with at least one member selected from the group consisting of C1-C10 straight-chain or branched-chain alkyl and phenyl groups, The ring or six-membered ring may contain one or more hetero atoms selected from an oxygen atom, a nitrogen atom and a sulfur atom;

Y and Ar1 may be connected to form a 5-membered ring or a 6-membered ring which is substituted or unsubstituted with at least one member selected from the group consisting of C1-C10 straight-chain or branched-chain alkyl and phenyl groups, May contain one or more hetero atoms selected from an oxygen atom, a nitrogen atom and a sulfur atom.

Specifically, the compound represented by the formula (1) may be any one of the compounds represented by the following formulas (2) to (6).

(2)

(3)

≪ Formula 4 >

≪ Formula 5 >

(6)

In the above formulas 2 to 6,

R1 is hydrogen, halogen, _{nitrile, CF 3, -Si (CH 3} ) 3, linear or branched C1 ~ C10 linear or branched alkyl, C1 ~ C10 alkoxy, phenyl or pyridinyl group, or; or

Halogen, _{nitrile, CF 3, -Si (CH 3} ) 3, C1 ~ C10 straight or branched chain alkyl, C1 ~ C10 linear or branched alkoxy, phenyl, _{pyridinyl, -N (C 6 H 5)} 2 and Substituted or unsubstituted < RTI ID = 0.0 >

Phenyl, pyridinyl, triazinyl, naphthyl, 9,9-dimethylfluorenyl, dibenzofuranyl, dibenzothiophene, carbazole or -N (C ₆ H ₅ ) ₂ group;

L2 is a simple bond; Or naphthalene substituted or unsubstituted with a phenyl group, biphenyl substituted or unsubstituted with a phenyl group, 9,9-dimethylfluorene substituted or unsubstituted with a phenyl group, or substituted or unsubstituted phenyl group Is a divalent moiety of unsubstituted- (9,9-dimethylfluorene) - (phenyl) -;

X is a carbon atom or a nitrogen atom;

Z is deuterium, halogen, _{nitrile, CF 3, -Si (CH 3} ) 3, a C1 ~ C10 linear or branched alkyl, linear or branched C1 ~ C10 alkoxy, pyridinyl and 9,9-dimethyl fluorenyl flow carbonyl Or a substituted or unsubstituted < RTI ID = 0.0 >

이며,Straight or branched chain alkyl of C1 to C10, phenyl, pyridinyl, triazinyl, naphthyl, 9,9-dimethylfluorenyl, dibenzofuranyl, dibenzothiophene, carbazole, or

Lt;

Wherein R2 and R3 are, each independently, halogen, _{nitrile, CF 3, -Si (CH 3} ) 3, C1 ~ C10 straight or branched chain alkyl, C1 ~ C10 linear or branched alkoxy, phenyl, pyridinyl and -N (C ₆ H ₅ ) ₂ , or a substituted or unsubstituted

Straight or branched chain alkyl of C1 to C10, phenyl, pyridinyl, triazinyl, naphthyl, 9,9-dimethylfluorenyl, dibenzofuranyl, dibenzothiophene or carbazole group,

Wherein L2 and R2 or R3 are connected to each other to form a 5-membered ring or a 6-membered ring which is substituted or unsubstituted with at least one member selected from the group consisting of C1-C10 straight-chain or branched-chain alkyl and phenyl groups,

The R2 or R3 may be connected to form a 5-membered or 6-membered ring, which is substituted or unsubstituted with at least one member selected from the group consisting of C1-C10 straight-chain or branched-chain alkyl and phenyl, An oxygen atom, a nitrogen atom and a sulfur atom;

Ar1, Ar2, Ar3, Ar4, Ar5, Ar6 and Ar7 are each independently a heavy hydrogen, a halogen, a _{nitrile, CF 3, -Si (CH 3} ) 3, C1 ~ C10 linear or branched alkyl, C1 ~ C10 of Straight or branched chain alkoxy; -N (C ₆ H ₅ ) ₂ or a carbazole-substituted or unsubstituted Phenyl; Pyridinyl, and -N (C ₆ H ₅ ) ₂ , or a substituted or unsubstituted

Phenyl, pyridinyl, triazinyl, naphthyl, 9,9-dimethyl fluorenyl flow carbonyl, dibenzo-furanyl, dibenzothiophene, carbazole and the sol or _{-N (C 6 H 5) 2} ,

At least one carbon atom, a nitrogen atom, an oxygen atom, or a sulfur atom of Ar5 and N adjacent to Ar5 may be substituted or unsubstituted with at least one member selected from the group consisting of C1-C10 linear or branched alkyl and phenyl groups A 5-membered ring or a 6-membered ring and may be fused to a ring containing X,

Ar 1 and Ar 5, Ar 3 and Ar 4, Ar 6 and Ar 7 are each independently a 5-membered ring substituted with at least one member selected from the group consisting of a straight-chain or branched-chain alkyl group having 1 to 10 carbon atoms and a phenyl group, And the 5-membered or 6-membered ring may contain one or more heteroatoms selected from an oxygen atom, a nitrogen atom and a sulfur atom;

Wherein L2 or Z and Ar3 may be connected to form a 5-membered ring or a 6-membered ring which is substituted or unsubstituted with at least one member selected from the group consisting of C1-C10 straight-chain or branched-chain alkyl and phenyl groups, Or the 6-membered ring may contain one or more hetero atoms selected from an oxygen atom, a nitrogen atom and a sulfur atom;

Wherein R4 is hydrogen, phenyl or -N (C ₆ H _{5) 2,} and;

R5, R6, R7 and R8 are each independently hydrogen; A halogen, a nitrile, a _{CF 3, -Si (CH 3)} 3, C1 ~ C10 straight or branched chain alkyl, C1 ~ C10 linear or branched alkoxy, phenyl, pyridinyl, and -N of (C ₆ H _{5) 2} Substituted or unsubstituted < RTI ID = 0.0 >

A straight or branched chain alkyl of C1 to C10, phenyl, pyridinyl, triazinyl, naphthyl, 9,9-dimethylfluorenyl, dibenzofuranyl, dibenzothiophene or carbazole group,

In the above formulas (4) and (5)

At least one carbon atom, a nitrogen atom, an oxygen atom or a sulfur atom of Ar6 and N adjacent to Ar6 are substituted or unsubstituted with at least one member selected from the group consisting of C1-C10 linear or branched alkyl and phenyl groups, A 5-membered ring or a 6-membered ring to which the N adjacent to Ar < 6 > may be fused to the phenylene ring,

In Formula 5,

At least one carbon atom, a nitrogen atom, an oxygen atom, or a sulfur atom of Ar3 and N adjacent to Ar3 may be substituted or unsubstituted with at least one member selected from the group consisting of C1 to C10 linear or branched alkyl and phenyl groups A 5-membered ring or a 6-membered ring may be fused to a phenylene ring to which N adjacent to Ar 3 is connected.

More specifically, in the organic electroluminescent compound represented by any one of Chemical Formulas 2 to 6,

R1 is hydrogen or a C1 to C5 linear or branched alkyl group;

L2 is a simple bond, a divalent moiety of phenyl, naphthalene, biphenylene, 9,9-dimethylfluorene or - (9,9-dimethylfluorene) - (phenyl) - substituted or unsubstituted with a phenyl group;

X is a carbon atom or a nitrogen atom;

Z is deuterium, halogen, _{nitrile, CF 3, -Si (CH 3} ) 3, a C1 ~ C5 linear or branched alkyl, linear or branched C1 ~ C5 alkoxy, pyridinyl and 9,9-dimethyl fluorenyl flow carbonyl Or a substituted or unsubstituted < RTI ID = 0.0 >

이며,Phenyl, pyridinyl, naphthyl, 9,9-dimethylfluorenyl, dibenzofuranyl or

Lt;

R2 and R3 are each independently a C1-C10 linear or branched alkyl, phenyl, naphthyl or 9,9-dimethylfluorenyl group substituted or unsubstituted with a C1-C5 linear or branched alkyl group,

In the above, L2 and R2 or R3 may be connected to form a 5-membered ring or a 6-membered ring substituted or unsubstituted with at least one C1-C5 straight-chain or branched-chain alkyl group,

The R2 and R3 may be connected to form a 5-membered ring or a 6-membered ring substituted or unsubstituted with at least one C1-C5 linear or branched alkyl group, and the 5-membered ring or 6-membered ring may be an oxygen atom, a nitrogen atom, Lt; RTI ID = 0.0 > 1, < / RTI >

Ar1, Ar2, Ar3, Ar4, Ar5, Ar6 and Ar7 are each independently a heavy hydrogen, a halogen, a _{nitrile, CF 3, -Si (CH 3} ) 3, straight-chain or branched-chain alkyl of C1 ~ C5, C1 ~ C5 Straight or branched chain alkoxy; -N (C ₆ H ₅ ) ₂ or a carbazole-substituted or unsubstituted Phenyl; Pyridinyl, and -N (C ₆ H ₅ ) ₂ , or a substituted or unsubstituted

Phenyl, pyridinyl, triazinyl, naphthyl, 9,9-dimethyl fluorenyl flow carbonyl, dibenzo-furanyl, dibenzothiophene, carbazole and the sol or _{-N (C 6 H 5) 2} ,

At least one carbon atom, a nitrogen atom, an oxygen atom or a sulfur atom of Ar5 and N adjacent to Ar5 may be substituted or unsubstituted with at least one member selected from the group consisting of C1 to C5 linear or branched alkyl and phenyl groups A 5-membered ring or a 6-membered ring and may be fused to a ring containing X, and the 5-membered or 6-membered ring may further include at least one heteroatom selected from an oxygen atom, a nitrogen atom and a sulfur atom,

Ar 1 and Ar 5, Ar 3 and Ar 4, and Ar 6 and Ar 7 are each independently connected to form a 5-membered ring which is substituted or unsubstituted with at least one member selected from the group consisting of C 1 to C 5 linear or branched alkyl and phenyl groups Or a 6-membered ring, and the 5-membered or 6-membered ring may contain one or more hetero atoms selected from an oxygen atom, a nitrogen atom and a sulfur atom;

Wherein L2 or Z and Ar3 may be connected to form a 5-membered ring or a 6-membered ring which is substituted or unsubstituted with at least one member selected from the group consisting of C1-C5 straight-chain or branched-chain alkyl and phenyl groups, Or the 6-membered ring may contain one or more hetero atoms selected from an oxygen atom, a nitrogen atom and a sulfur atom;

Wherein R4 is hydrogen or -N (C ₆ H _{5) 2} group;

R5, R6, R7 and R8 are each independently hydrogen or a linear or branched alkyl group having from 1 to 5 carbon atoms.

In the above formulas 4 and 5,

At least one carbon atom, a nitrogen atom, an oxygen atom, or a sulfur atom of Ar6 and N adjacent to Ar6 are taken together with at least one substituent selected from the group consisting of C1 to C5 linear or branched alkyl and phenyl groups, A 5-membered ring or a 6-membered ring may be fused to the phenylene ring to which the N adjacent to Ar 6 is connected.

In Formula 5,

At least one carbon atom, a nitrogen atom, an oxygen atom or a sulfur atom of Ar3 and N adjacent to Ar3 are taken together with at least one group selected from the group consisting of C1 to C5 linear or branched alkyl and phenyl groups, A 5-membered ring or a 6-membered ring may be fused to a phenylene ring to which N adjacent to Ar 3 is connected.

The organic electroluminescent compound may be useful as a phosphorescent material such as a phosphorescent green host material, a hole injecting layer material, a hole transporting layer material, an electron injecting layer material or an electron transporting layer material, and more particularly, a hole transporting layer material and a phosphorescent green host material Can be preferably used.

The organic electroluminescent compound may have a chemical structure of any one of the compounds 1 to 300 shown in Table 1 below.

The organic electroluminescent compound may be used as a phosphorescent green host material, a hole injecting layer material, a hole transporting layer material, an electron injecting layer material, or an electron transporting layer material in a material for an organic EL device.

In one embodiment, the organic electroluminescent compound can be used as a phosphorescent green host material or a hole transport layer material.

According to another embodiment of the present invention, there is provided an organic electroluminescent device in which one or more organic thin film layers including at least a light emitting layer are sandwiched between a cathode and an anode, wherein at least one of the organic thin film layers is the organic electroluminescent compound Are contained singly or in combination of two or more kinds.

The organic thin film layer may be formed by a soluble process using the organic electroluminescent compound.

The organic electroluminescent compound may be included in an organic electroluminescent device as a phosphorescent green host material, a hole injecting layer material, a hole transporting layer material, an electron injecting layer material, or an electron transporting layer material, and is particularly useful as a hole transporting layer material and a phosphorescent green host material Lt; / RTI >

The organic electroluminescent device may further include:

An anode, a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, an electron injecting layer, and a cathode stacked in this order.

In another embodiment of the present invention, there is provided an electronic device including the organic electroluminescent device.

The electronic device including the organic electroluminescent device includes an organic integrated circuit (O-IC), an organic field effect transistor (O-FET), an organic thin film transistor (O-TFT), an organic light emitting transistor (O- (O-SC), an organic optical detector, an organic photoreceptor, an organic field-quenching device (O-FQD), a luminescent electrochemical cell (LEC), an organic laser diode (O- ).

Hereinafter, the organic electroluminescent device will be described by way of example. However, the following examples do not limit the organic electroluminescent device of the present invention.

The organic electroluminescent device may have a structure in which an anode (a hole injecting electrode), a hole injecting layer (HIL) and / or a hole transporting layer (HTL), a light emitting layer (EML), and a cathode (electron injecting electrode) Preferably, an electron blocking layer (EBL) may be additionally provided between the anode and the light emitting layer, and an electron transport layer (ETL), an electron injection layer (EIL) or a hole blocking layer (HBL) may be further interposed between the cathode and the light emitting layer.

In the method of manufacturing the organic electroluminescence device, a cathode material is coated on the surface of a substrate by a conventional method to form a cathode. At this time, the substrate to be used is preferably a glass substrate or a transparent plastic substrate having excellent transparency, surface smoothness, ease of handling, and waterproofness. As the material for the positive electrode, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO) and the like which are transparent and excellent in conductivity may be used.

Next, a hole injection layer (HIL) material is formed on the surface of the anode by vacuum thermal deposition or spin coating using a conventional method. As the hole injection layer material, the organic electroluminescent compound may be used. In addition, copper phthalocyanine (CuPc), 4,4 ', 4 "-tris (3-methylphenylamino) triphenylamine (m-MTDATA) , 4 ', 4 "-tris (3-methylphenylamino) phenoxybenzene (m-MTDAPB), and starburst type amines 4,4' TCTA), 4,4 ', 4 "-tris (N- (2-naphthyl) -N-phenylamino) -triphenylamine (2-TNATA) or IDE406 available from Idemitsu have.

A hole transport layer (HTL) material is vacuum-deposited or spin coated on the surface of the hole injection layer by a conventional method to form a hole transport layer. As the hole transport layer material, the organic electroluminescent compound may be used. In addition, bis (N- (1-naphthyl-n-phenyl)) benzidine (? -NPD), N, N'- (NPB) or N, N'-biphenyl-N, N'-bis (3-methylphenyl) -1,1'-biphenyl- - diamine (TPD).

A light emitting layer (EML) material is formed on the surface of the hole transport layer by vacuum thermal deposition or spin coating using a conventional method. In this case, the organic electroluminescent compound may be used as a phosphorescent green host material, and the tris (8-hydroxyquinolinolato) aluminum (Alq3) (8-hydroxyquinoline beryllium salt), DPVBi (4,4'-bis (2,2-biphenylethenyl) -1,1'-biphenyl) series, Spiro ) Material, a spiro-DPVBi (spiro-4,4'-bis (2,2-biphenylethenyl) -1,1'-biphenyl), LiPBO (2- (2-benzoxazolyl) Lithium salt), bis (biphenylvinyl) benzene, aluminum-quinoline metal complex, imidazole, thiazole and oxazole metal complexes.

Among the light emitting layer materials, IDE102 and IDE105 available from Idemitsu as phosphorescent dopants and tris (2-phenylpyridine) iridium (III) (Ir (ppy ) 3), iridium (III) bis [(4,6-difluorophenyl) pyridinate-N, C-2 '] picolinate (FIrpic) (Chihaya Adachi et al., Appl. Phys Platy (II) octaethylporphyrin (PtOEP), TBE002 (Cobion), etc. may be used.

An electron transport layer (ETL) material is formed on the surface of the light emitting layer by vacuum thermal deposition or spin coating using a conventional method. At this time, the electron transport layer material used may be the organic electroluminescent compound described above, and tris (8-hydroxyquinolinolato) aluminum (Alq3) or the like may be used.

Alternatively, by further forming a hole blocking layer (HBL) between the light emitting layer and the electron transporting layer and using a phosphorescent dopant together with the light emitting layer, it is possible to prevent the phenomenon that the triplet excitons or holes are diffused into the electron transporting layer.

The hole blocking layer can be formed by vacuum thermal deposition and spin coating using a hole blocking layer material in a conventional manner. In the case of the hole blocking layer material, there is no particular limitation, but (8-hydroxyquinolinolato Lithium biphenoxide (BAlq), bathocuproine (BCP), LiF, etc. may be used as the lithium salt (Li), bis (8-hydroxy-2-methylquinolinonato)

An electron injection layer (EIL) material is formed on the surface of the electron transport layer by vacuum thermal deposition or spin coating using a conventional method. As the electron injection layer material used herein, the organic electroluminescent compound may be used. In addition, materials such as LiF, Liq, Li2O, BaO, NaCl, and CsF may be used.

Finally, a negative electrode is formed on the surface of the electron injecting layer by vacuum thermal deposition using a conventional method.

At this time, as the negative electrode material to be used, lithium, aluminum, aluminum-lithium, calcium, magnesium, (Mg-Ag) or the like may be used. In the case of a top emission organic electroluminescent device, indium tin oxide (ITO) or indium zinc oxide (IZO) may be used to form a transparent cathode capable of transmitting light.

The organic electroluminescent device may be manufactured in the order as described above, that is, in the order of anode / hole injection layer / hole transport layer / light emitting layer / hole blocking layer / electron transport layer / electron injection layer / cathode, / Electron transporting layer / hole blocking layer / light emitting layer / hole transporting layer / hole injecting layer / anode.

Hereinafter, a method of synthesizing the above compounds will be described with reference to representative examples. However, the method of synthesizing the above compounds is not limited to the following exemplified methods, and the compounds can be prepared by the methods exemplified below and by methods known in the art.

Synthesis of Compound [1]

[Reaction Scheme 1]

Preparation of intermediate compound [1-1]

To the reaction flask was added 10 g (31.76 mmol) of 1,3,5-tribromobenzene, 10.1 g (34.94 mmol) of (4- (diphenylamino) phenyl) boronic acid, 0.36 g of tetrakis (triphenylphosphine) palladium 5.27 g (38.12 mmol) of potassium carbonate (K ₂ CO ₃ ) was added thereto, and the mixture was refluxed under stirring in a nitrogen stream for 12 hours with 100 ml of toluene and 10 ml of purified water. After completion of the reaction, the reaction mixture was slowly cooled to room temperature, and then the reaction solution was poured into a saturated aqueous solution of ammonium chloride and extracted with ethyl acetate. The organic layer was separated, dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure and purified by column chromatography to obtain 8.5 g (56%) of intermediate compound [1-1] as a white solid.

Preparation of intermediate compound [1-2]

Intermediate compound to a reaction flask [1-1] 8.2g (17.11mmol), phenyl boronic acid 2.3g (18.82mmol), tetrakis (triphenylphosphine) palladium, 0.2g (0.17mmol), potassium carbonate (K ₂ CO ₃ ), And the mixture was stirred under reflux for 12 hours with 100 ml of toluene and 10 ml of purified water under a nitrogen stream. After completion of the reaction, the reaction mixture was slowly cooled to room temperature, and then the reaction solution was poured into a saturated aqueous solution of ammonium chloride and extracted with ethyl acetate. The organic layer was separated, dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure and purified by column chromatography to obtain 5.1 g (62%) of an intermediate compound [1-2] as a white solid.

Preparation of compound [1]

To the reaction flask was added 4.7 g (9.86 mmol) of intermediate compound [1-2], 1.83 g (10.85 mmol) of diphenylamine, 22 mg (0.1 mmol) of palladium (II) acetate and 0.05 mL 0.193 mmol) and 1.33 g (13.81 mmol) of sodium butoxide were added thereto, and the mixture was refluxed and stirred for 12 hours with 100 mL of toluene under a nitrogen stream. After completion of the reaction, the reaction mixture was slowly cooled to room temperature, and then the reaction solution was poured into a saturated aqueous solution of ammonium chloride and extracted with ethyl acetate. The organic layer was separated, dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure and purified by column chromatography to obtain 4.2 g (76%) of the target compound [1] as a white solid.

^{1 H NMR (300 MHz, CDCl} 3): δ 7.62 ~ 7.57 (m, 8H), 7.47 ~ 7.40 (m, 8H), 7.36 ~ 7.21 (m, 14H), 7.07 ~ 7.03 (t, 2H)

MS / FAB: 564 (M ^< ^{+ &} gt ^; ).

Synthesis of Compound [83]

[Reaction Scheme 2]

Preparation of intermediate compound [83-1]

To the reaction flask was added 10 g (31.76 mmol) of 1,3,5-tribromobenzene, 10 g (34.94 mmol) of (9-phenyl-9H-carbazol- And 5.27 g (38.12 mmol) of potassium carbonate (K ₂ CO ₃ ) were added thereto, and the mixture was refluxed under stirring in a nitrogen stream for 12 hours with 100 ml of toluene and 10 ml of purified water. After completion of the reaction, the reaction mixture was slowly cooled to room temperature, and then the reaction solution was poured into a saturated aqueous solution of ammonium chloride and extracted with ethyl acetate. The organic layer was separated, dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure and purified by column chromatography to obtain 7.7 g (51%) of intermediate compound [83-1] as a white solid.

Preparation of intermediate compound [83-2]

Intermediate compound [83-1] 7.5g into the reaction flask (15.72mmol), phenyl boronic acid 2.1g (17.29mmol), tetrakis (triphenylphosphine) palladium, 0.18g (0.16mmol), potassium carbonate (K ₂ CO ₃ ), And the mixture was stirred under reflux for 12 hours with 100 ml of toluene and 10 ml of purified water under a nitrogen stream. After completion of the reaction, the reaction mixture was slowly cooled to room temperature, and then the reaction solution was poured into a saturated aqueous solution of ammonium chloride and extracted with ethyl acetate. The organic layer was separated, dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure and purified by column chromatography to obtain 4.3 g (58%) of an intermediate compound [83-2] as a white solid.

Preparation of compound [83]

To the reaction flask was added 4 g (8.43 mmol) of the intermediate compound [83-2], 1.57 g (9.27 mmol) of diphenylamine, 20 mg (0.08 mmol) of palladium (II) acetate, 0.04 mL mmol) and 1.13 g (11.8 mmol) of sodium tert-butoxide were added thereto, and the mixture was stirred under reflux for 12 hours with 100 mL of toluene under a nitrogen stream. After completion of the reaction, the reaction mixture was slowly cooled to room temperature, and then the reaction solution was poured into a saturated aqueous solution of ammonium chloride and extracted with ethyl acetate. The organic layer was separated, dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure and purified by column chromatography to obtain 3.4 g (71%) of the target compound [83] as a white solid.

^{1 H NMR (300 MHz, CDCl} 3): δ 8.34 (s, 1H), 8.20 ~ 8.18 (d, 1H), 7.64 ~ 7.59 (m, 8H), 7.46 ~ 7.43 (m, 6H), 7.34 ~ 7.25 ( m, 12H), 7.09 ~ 7.05 (t, 2H)

MS / FAB: 562 (M ^< ^{+ &} gt ^; ).

Synthesis of Compound [84]

[Reaction Scheme 3]

Preparation of compound [84]

To the reaction flask were added 4 g (8.43 mmol) of the intermediate compound [83-2], 3.12 g (9.27 mmol) of N1, N1, N4-triphenylbenzene-1,4-diamine, 20 mg (0.08 mmol) 0.04 mL (0.16 mmol) of triethylbutylphosphine (50%) and 1.13 g (11.8 mmol) of sodium butoxide were added thereto, and the mixture was refluxed and stirred for 12 hours with 100 mL of toluene under a nitrogen stream. After completion of the reaction, the reaction mixture was slowly cooled to room temperature, and then the reaction solution was poured into a saturated aqueous solution of ammonium chloride and extracted with ethyl acetate. The organic layer was separated, dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure and purified by column chromatography to obtain 4.2 g (68%) of the target compound [84] as a white solid.

^{1 H NMR (300 MHz, CDCl} 3): δ 8.35 (s, 1H), 8.22 ~ 8.18 (d, 1H), 7.66 ~ 7.58 (m, 8H), 7.50 ~ 7.41 (m, 10H), 7.36 ~ 7.22 ( m, 16H), 7.11 ~ 7.06 (m, 3H)

MS / FAB: 729 (M < + >).

Synthesis of Compound [86]

[Reaction Scheme 4]

Preparation of compound [86]

To the reaction flask were added 4 g (8.43 mmol) of the intermediate compound [83-2], 3.1 g (9.27 mmol) of N, 9-diphenyl-9H-carbazol-3-amine, 20 mg (0.08 mmol) 0.04 mL (0.16 mmol) of tert-butylphosphine (50%) and 1.13 g (11.8 mmol) of sodium tert-butoxide were added and refluxed with 100 mL of toluene for 12 hours under a nitrogen stream. After completion of the reaction, the reaction mixture was slowly cooled to room temperature, and then the reaction solution was poured into a saturated aqueous solution of ammonium chloride and extracted with ethyl acetate. The organic layer was separated, dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure and purified by column chromatography to obtain 3.5 g (57%) of the target compound [86] as a white solid.

^{1 H NMR (300 MHz, CDCl} 3): δ 8.34 ~ 8.31 (d, 2H), 8.24 ~ 8.18 (d, 2H), 7.65 ~ 7.55 (m, 8H), 7.48 ~ 7.40 (m, 8H), 7.33 ~ 7.19 (m, 14H), 7.08 ~ 7.02 (m, 3H)

MS / FAB: 727 (M ^< ^{+ &} gt ^; ) [

Hereinafter, the present invention will be described in more detail by way of examples. However, the following examples are intended to further illustrate the present invention, and the scope of the present invention is not limited by the following examples. The following examples can be appropriately modified and changed by those skilled in the art within the scope of the present invention.

Comparative Example  1: Manufacture of organic electroluminescent device

Wherein the compound represented by the following formula (a) is used as a phosphorescent green host and the compound represented by the following formula (c) is used as a phosphorescent green dopant, and 2-TNATA (4,4 ' NPD (N, N'-di (naphthalene-1-yl) -N, N'-diphenylbenzidine) was used as a hole transport layer material d), an organic electroluminescent device having the following structure was fabricated: ITO / 2-TNATA (80 nm) /? -NPD (30 nm) / formula a + c 30 nm / Alq3 30 nm) / Liq (1 nm) / Al (100 nm).

The anode was prepared by cutting Corning's 15 Ω / cm ₂ (1000 Å) ITO glass substrate to a size of 25 mm × 25 mm × 0.7 mm, ultrasonically cleaning it in acetone isopropyl alcohol and pure water for 15 minutes each, UV ozone cleaning was used. 2-TNATA was vacuum deposited on the substrate to form a hole injection layer having a thickness of 80 nm. On top of the hole injection layer, α-NPD was vacuum deposited to form a hole transport layer having a thickness of 30 nm. A compound represented by Formula (a) and a compound represented by Formula (c) (doping ratio: 10%) were vacuum deposited on the hole transport layer to form a light emitting layer with a thickness of 30 nm. Then, an Alq3 compound was vacuum deposited on the light emitting layer to a thickness of 30 nm to form an electron transporting layer. Liq 1 nm (electron injecting layer) and Al 100 nm (cathode) were sequentially vacuum-deposited on the electron transporting layer to form an organic electroluminescent device as shown in Table 2. [

Comparative Example  2: Manufacture of organic electroluminescent device

Wherein the compound represented by the following formula (b) is used as a phosphorescent green host and the compound represented by the following formula (c) is used as a phosphorescent green dopant, and 2-TNATA (4,4 ' (N, N'-di (naphthylene-1-yl) -N, N'-diphenylbenzidine) was used as a hole transport layer material (30 nm) / Alq3 (30 nm) / a-NPD (30 nm) / formula b + formula c (30 nm) / Alq3 Liq (1 nM) / Al (100 nM).

An anode was prepared by cutting Corning's 15 Ω / cm 2 (1000 Å) ITO glass substrate to a size of 25 mm × 25 mm × 0.7 mm, ultrasonically cleaning it in acetone isopropyl alcohol and pure water for 15 minutes each, Ozone cleaning was used. 2-TNATA was vacuum deposited on the substrate to form a hole injection layer having a thickness of 80 nm. On top of the hole injection layer,? -NPD was vacuum deposited to form a hole transport layer having a thickness of 30 nm. A compound represented by the formula (b) and a compound represented by the formula (c) (doping ratio: 10%) were vacuum deposited on the hole transport layer to form a light emitting layer with a thickness of 30 nm. Then, an Alq3 compound was vacuum deposited on the light emitting layer to a thickness of 30 nm to form an electron transporting layer. Liq 1 nm (electron injecting layer) and Al 100 nm (cathode) were sequentially vacuum-deposited on the electron transporting layer to form an organic electroluminescent device as shown in Table 2. [

<Formula a> <Formula b>

<Formula c> <Formula d>

Example  1 to 5: Manufacture of Organic Electroluminescent Device

In the same manner as in Comparative Example 1, except that the compounds represented by the formulas (5), (48), (112), (175) and (227) (30 nm) / Alq3 (30 nm) / Liq (10 nm) / Al (30 nm) / Compound 5, 48, 112, 175 or 227 (100 nm) was fabricated.

Evaluation example  One: Comparative Example  1, 2, and Example  Evaluation of luminescent characteristics of organic electroluminescent devices 1 to 5

The luminescence brightness, the luminescence efficiency and the luminescence peak were evaluated by using Keithley source meter "2400" and KONIKA MINOLTA "CS-2000" for the organic EL devices of Comparative Examples 1 and 2 and Examples 1 to 5, Are shown in Table 2 below. The above examples showed green emission peak values in the range of 513 to 515 nm.

Example No. 2. Hole transportation
material
No. Voltage
OP. V Luminance
[cd / m ² ] efficiency
[cd / A] Emission peak
[nm] Comparative Example 1 d 6.0 3372 33.72 511 Comparative Example 2 d 5.8 3513 35.13 513 One 5 4.60 4322 43.22 515 2 48 5.37 4630 46.30 513 3 112 4.75 4245 42.45 513 4 175 5.34 4935 49.35 513 5 227 4.81 4981 49.81 514

As shown in Table 2, the organic electroluminescent devices of Examples 1 to 5 exhibited improved luminescent characteristics as compared with Comparative Examples 1 and 2.

Evaluation example  2: Comparative Example  1, 2, and Example  Evaluation of lifetime characteristics of organic electroluminescent devices

The organic EL devices of Comparative Examples 1 and 2 and Examples 1 to 5 were measured for time to reach 97% on the basis of 3000 nits using an LTS-1004AC lifetime measuring device manufactured by ENC technology, The results are shown in Table 3 below.

Example No. 2. Hole transportation
material
No. life span
Time [Hours] Comparative Example 1 d 45 Comparative Example 2 d 53 One 5 74 2 48 84 3 112 69 4 175 83 5 227 60

As shown in Table 3, the organic electroluminescent devices of Examples 1 to 5 exhibited improved lifetime characteristics as compared with Comparative Examples 1 and 2.

Example  6 to 10: Preparation of Organic Electroluminescent Device

In the same manner as in Comparative Example 1, except that phosphorescent green host (a) was used instead of the phosphorescent green host in the above Comparative Example 1, and the phosphorescent green host was used in place of the phosphorescent green host represented by the formula (52), 131,164, (30 nm) / Alq ₃ (30 nm) / Liq (30 nm) / (30 nm) / [ITO / 2-TNATA 1 nm) / Al (100 nm).

Evaluation example  3: Comparative Example  1, 2, and Example  Evaluation of luminescence characteristics of 6 to 10

The luminescence brightness, the luminescence efficiency and the luminescence peak were evaluated by using Keithley ssource meter "2400" and KONIKA MINOLTA "CS-2000" for the organic EL devices of Comparative Examples 1 and 2 and Examples 6 to 10, Are shown in Table 4 below. The above examples showed green emission peak values in the range of 513 to 515 nm.

Example No. 2. Phosphorescent green host
No. Voltage
OP. V Luminance
[cd / m ² ] efficiency
[cd / A] Emission peak
[nm] Comparative Example 1 a 6.0 3372 33.72 511 Comparative Example 2 b 5.8 3513 35.13 513 6 52 4.72 4805 48.05 515 7 131 4.76 4491 44.91 513 8 164 5.02 4252 42.52 515 9 211 5.12 4759 47.59 514 10 245 4.89 4652 46.52 513

As shown in Table 4, the organic electroluminescent devices of Examples 6 to 10 exhibited improved luminescent characteristics as compared with Comparative Examples 1 and 2.

Evaluation example  4: Comparative Example  1, 2, and Example  Evaluation of lifetime characteristics of organic electroluminescent devices

The organic EL devices of Comparative Examples 1 and 2 and Examples 6 to 10 were measured for time to reach 97% on the basis of 3000 nits using an LTS-1004AC life measuring device manufactured by ENC technology, The results are shown in Table 5 below.

Example No. 2. Phosphorescent green host
No. life span
Time [Hours] Comparative Example 1 a 45 Comparative Example 2 b 53 6 52 58 7 131 61 8 164 55 9 211 70 10 245 69

As shown in Table 5, the organic electroluminescent devices of Examples 6 to 10 exhibited improved lifetime characteristics as compared with Comparative Examples 1 and 2.

While the present invention has been particularly shown and described with reference to exemplary embodiments thereof, it is to be understood that the invention is not limited to the disclosed exemplary embodiments, And falls within the scope of the invention.

Claims (12)

An organic electroluminescent compound represented by the following Formula 1:
&Lt; Formula 1 >

In this formula,
R1 is hydrogen, halogen, _{nitrile, CF 3, -Si (CH 3} ) 3, linear or branched C1 ~ C10 linear or branched alkyl, C1 ~ C10 alkoxy, phenyl or pyridinyl group, or; or
Halogen, _{nitrile, CF 3, -Si (CH 3} ) 3, C1 ~ C10 straight or branched chain alkyl, C1 ~ C10 linear or branched alkoxy, phenyl, _{pyridinyl, -N (C 6 H 5)} 2 and Substituted or unsubstituted &lt; RTI ID = 0.0 &gt;
Phenyl, pyridinyl, triazinyl, naphthyl, 9,9-dimethylfluorenyl, dibenzofuranyl, dibenzothiophene, carbazole, or -N (C ₆ H ₅ ) ₂ group;
L1 is a simple bond; Phenyl or -N (C ₆ H ₅ ) ₂ , Phenyl; Or a divalent moiety of pyridine;
L2 is a simple bond; Or phenyl substituted or unsubstituted with a phenyl group, naphthalene substituted or unsubstituted with a phenyl group, biphenyl substituted or unsubstituted with a phenyl group, 9,9-dimethylfluorene substituted or unsubstituted with a phenyl group, or substituted or unsubstituted phenyl group Is a divalent moiety of a substituted - (9,9-dimethylfluorene) - (phenyl);
X is a carbon atom or a nitrogen atom;
Y is an aromatic ring; Or a C1-C10 linear or branched alkyl group substituted or unsubstituted with at least one member selected from the group consisting of C1-C10 alkyl groups and phenyl groups,
The aromatic ring is deuterium; halogen; Nitrile; CF _3; -Si (CH _{3) 3;} C1 to C10 straight or branched chain alkyl; Straight or branched chain alkoxy of C1 to C10; -N (C ₆ H ₅ ) ₂ or a substituted or unsubstituted Phenyl; Pyridinyl; And -N (C ₆ H ₅₎ in one or more selected from the group consisting of a _{2-substituted} or unsubstituted
Phenyl, pyridinyl, triazinyl, naphthyl, 9,9-dimethylfluorenyl, dibenzofuranyl, dibenzothiophene, carbazole or -N (C ₆ H ₅ ) ₂ ;
Z is deuterium, halogen, _{nitrile, CF 3, -Si (CH 3} ) 3, a C1 ~ C10 linear or branched alkyl, linear or branched C1 ~ C10 alkoxy, pyridinyl and 9,9-dimethyl fluorenyl flow carbonyl Or a substituted or unsubstituted &lt; RTI ID = 0.0 &gt;
Straight or branched chain alkyl of C1 to C10, phenyl, pyridinyl, triazinyl, naphthyl, 9,9-dimethylfluorenyl, dibenzofuranyl, dibenzothiophene, carbazole or

Lt;
R2 and R3 are each independently selected from the group consisting of C1 to C10 linear or branched alkyl, C1 to C10 linear or branched alkoxy, Phenyl, pyridinyl, and -N (C ₆ H ₅ ) ₂ , or a substituted or unsubstituted
A straight or branched chain alkyl of C1 to C10, phenyl, pyridinyl, triazinyl, naphthyl, 9,9-dimethylfluorenyl, dibenzofuranyl, dibenzothiophene, or carbazole group,
Wherein L2 and R2 or R3 may be connected to form a 5-membered ring or a 6-membered ring which is substituted or unsubstituted with at least one member selected from the group consisting of C1-C10 straight-chain or branched-chain alkyl and phenyl groups,
The R2 or R3 may be connected to form a 5-membered or 6-membered ring, which is substituted or unsubstituted with at least one member selected from the group consisting of C1-C10 straight-chain or branched-chain alkyl and phenyl, An oxygen atom, a nitrogen atom and a sulfur atom;
Wherein at least one carbon atom, nitrogen atom, oxygen atom or sulfur atom of Y and N adjacent to Y are substituted or unsubstituted with at least one group selected from the group consisting of C1 to C10 linear or branched alkyl and phenyl groups, A 5-membered ring or a 6-membered ring to be fused to a ring containing X;
Ar1, Ar2 and Ar3 are each independently selected from deuterium, halogen, _{nitrile, CF 3, -Si (CH 3} ) 3, straight-chain or branched-chain alkyl of C1 ~ C10, linear or branched C1 ~ C10 alkoxy; -N (C ₆ H ₅ ) ₂ or a substituted or unsubstituted Phenyl; Pyridinyl, carbazole, and -N (C ₆ H ₅ ) ₂ , or a substituted or unsubstituted
Phenyl, pyridinyl, triazinyl, naphthyl, 9,9-dimethylfluorenyl, dibenzofuranyl, dibenzothiophene, carbazole or -N (C ₆ H ₅ ) ₂ group;
Wherein L2 or Z and Ar3 may be connected to form a 5-membered ring or a 6-membered ring substituted or unsubstituted with at least one member selected from the group consisting of C1-C10 straight-chain or branched-chain alkyl and phenyl groups, The ring or six-membered ring may contain one or more hetero atoms selected from an oxygen atom, a nitrogen atom and a sulfur atom;
Y and Ar1 may be connected to form a 5-membered ring or a 6-membered ring which is substituted or unsubstituted with at least one member selected from the group consisting of C1-C10 straight-chain or branched-chain alkyl and phenyl groups, May contain one or more hetero atoms selected from an oxygen atom, a nitrogen atom and a sulfur atom.
The method according to claim 1,
The compound represented by the formula (1) is any one of the compounds represented by the following formulas (2) to (6)
Organic Electroluminescent Compound:
(2)

(3)

&Lt; Formula 4 >

&Lt; Formula 5 >

(6)

In the above formulas 2 to 6,
R1 is hydrogen, halogen, _{nitrile, CF 3, -Si (CH 3} ) 3, linear or branched C1 ~ C10 linear or branched alkyl, C1 ~ C10 alkoxy, phenyl or pyridinyl group, or; or
Halogen, _{nitrile, CF 3, -Si (CH 3} ) 3, C1 ~ C10 straight or branched chain alkyl, C1 ~ C10 linear or branched alkoxy, phenyl, _{pyridinyl, -N (C 6 H 5)} 2 and Substituted or unsubstituted < RTI ID = 0.0 >
Phenyl, pyridinyl, triazinyl, naphthyl, 9,9-dimethylfluorenyl, dibenzofuranyl, dibenzothiophene, carbazole or -N (C ₆ H ₅ ) ₂ group;
L2 is a simple bond; Or naphthalene substituted or unsubstituted with a phenyl group, biphenyl substituted or unsubstituted with a phenyl group, 9,9-dimethylfluorene substituted or unsubstituted with a phenyl group, or substituted or unsubstituted phenyl group Is a divalent moiety of unsubstituted- (9,9-dimethylfluorene) - (phenyl) -;
X is a carbon atom or a nitrogen atom;
Z is deuterium, halogen, _{nitrile, CF 3, -Si (CH 3} ) 3, a C1 ~ C10 linear or branched alkyl, linear or branched C1 ~ C10 alkoxy, pyridinyl and 9,9-dimethyl fluorenyl flow carbonyl Or a substituted or unsubstituted < RTI ID = 0.0 >
Straight or branched chain alkyl of C1 to C10, phenyl, pyridinyl, triazinyl, naphthyl, 9,9-dimethylfluorenyl, dibenzofuranyl, dibenzothiophene, carbazole, or

Lt;
Wherein R2 and R3 are, each independently, halogen, _{nitrile, CF 3, -Si (CH 3} ) 3, C1 ~ C10 straight or branched chain alkyl, C1 ~ C10 linear or branched alkoxy, phenyl, pyridinyl and -N (C ₆ H ₅ ) ₂ , or a substituted or unsubstituted
Straight or branched chain alkyl of C1 to C10, phenyl, pyridinyl, triazinyl, naphthyl, 9,9-dimethylfluorenyl, dibenzofuranyl, dibenzothiophene or carbazole group,
Wherein L2 and R2 or R3 are connected to each other to form a 5-membered ring or a 6-membered ring which is substituted or unsubstituted with at least one member selected from the group consisting of C1-C10 straight-chain or branched-chain alkyl and phenyl groups,
The R2 or R3 may be connected to form a 5-membered or 6-membered ring, which is substituted or unsubstituted with at least one member selected from the group consisting of C1-C10 straight-chain or branched-chain alkyl and phenyl, An oxygen atom, a nitrogen atom and a sulfur atom;
Ar1, Ar2, Ar3, Ar4, Ar5, Ar6 and Ar7 are each independently a heavy hydrogen, a halogen, a _{nitrile, CF 3, -Si (CH 3} ) 3, C1 ~ C10 linear or branched alkyl, C1 ~ C10 of Straight or branched chain alkoxy; -N (C ₆ H ₅ ) ₂ or a carbazole-substituted or unsubstituted Phenyl; Pyridinyl, and -N (C ₆ H ₅ ) ₂ , or a substituted or unsubstituted
Phenyl, pyridinyl, triazinyl, naphthyl, 9,9-dimethyl fluorenyl flow carbonyl, dibenzo-furanyl, dibenzothiophene, carbazole and the sol or _{-N (C 6 H 5) 2} ,
At least one carbon atom, a nitrogen atom, an oxygen atom, or a sulfur atom of Ar5 and N adjacent to Ar5 may be substituted or unsubstituted with at least one member selected from the group consisting of C1-C10 linear or branched alkyl and phenyl groups A 5-membered ring or a 6-membered ring and may be fused to a ring containing X,
Ar 1 and Ar 5, Ar 3 and Ar 4, Ar 6 and Ar 7 are each independently a 5-membered ring substituted with at least one member selected from the group consisting of a straight-chain or branched-chain alkyl group having 1 to 10 carbon atoms and a phenyl group, And the 5-membered or 6-membered ring may contain one or more heteroatoms selected from an oxygen atom, a nitrogen atom and a sulfur atom;
Wherein L2 or Z and Ar3 may be connected to form a 5-membered ring or a 6-membered ring which is substituted or unsubstituted with at least one member selected from the group consisting of C1-C10 straight-chain or branched-chain alkyl and phenyl groups, Or the 6-membered ring may contain one or more hetero atoms selected from an oxygen atom, a nitrogen atom and a sulfur atom;
Wherein R4 is hydrogen, phenyl or -N (C ₆ H _{5) 2,} and;
R5, R6, R7 and R8 are each independently hydrogen; A halogen, a nitrile, a _{CF 3, -Si (CH 3)} 3, C1 ~ C10 straight or branched chain alkyl, C1 ~ C10 linear or branched alkoxy, phenyl, pyridinyl, and -N of (C ₆ H _{5) 2} Substituted or unsubstituted < RTI ID = 0.0 >
A straight or branched chain alkyl of C1 to C10, phenyl, pyridinyl, triazinyl, naphthyl, 9,9-dimethylfluorenyl, dibenzofuranyl, dibenzothiophene or carbazole group,
In the above formulas (4) and (5)
At least one carbon atom, a nitrogen atom, an oxygen atom or a sulfur atom of Ar6 and N adjacent to Ar6 are substituted or unsubstituted with at least one member selected from the group consisting of C1-C10 linear or branched alkyl and phenyl groups, A 5-membered ring or a 6-membered ring to which the N adjacent to Ar &lt; 6 &gt; may be fused to the phenylene ring,
In Formula 5,
At least one carbon atom, a nitrogen atom, an oxygen atom, or a sulfur atom of Ar3 and N adjacent to Ar3 may be substituted or unsubstituted with at least one member selected from the group consisting of C1 to C10 linear or branched alkyl and phenyl groups A 5-membered ring or a 6-membered ring may be fused to a phenylene ring to which N adjacent to Ar 3 is connected.
3. The method of claim 2,
R1 is hydrogen or a C1 to C5 linear or branched alkyl group;
L2 is a simple bond, a divalent moiety of phenyl, naphthalene, biphenylene, 9,9-dimethylfluorene or - (9,9-dimethylfluorene) - (phenyl) - substituted or unsubstituted with a phenyl group;
X is a carbon atom or a nitrogen atom;
Z is deuterium, halogen, _{nitrile, CF 3, -Si (CH 3} ) 3, a C1 ~ C5 linear or branched alkyl, linear or branched C1 ~ C5 alkoxy, pyridinyl and 9,9-dimethyl fluorenyl flow carbonyl Or a substituted or unsubstituted &lt; RTI ID = 0.0 &gt;
Phenyl, pyridinyl, naphthyl, 9,9-dimethylfluorenyl, dibenzofuranyl or

Lt;
R2 and R3 are each independently a C1-C10 linear or branched alkyl, phenyl, naphthyl or 9,9-dimethylfluorenyl group substituted or unsubstituted with a C1-C5 linear or branched alkyl group,
In the above, L2 and R2 or R3 may be connected to form a 5-membered ring or a 6-membered ring substituted or unsubstituted with at least one C1-C5 straight-chain or branched-chain alkyl group,
The R2 and R3 may be connected to form a 5-membered ring or a 6-membered ring substituted or unsubstituted with at least one C1-C5 linear or branched alkyl group, and the 5-membered ring or 6-membered ring may be an oxygen atom, a nitrogen atom, Lt; RTI ID = 0.0 &gt; 1, &lt; / RTI &gt;
Ar1, Ar2, Ar3, Ar4, Ar5, Ar6 and Ar7 are each independently a heavy hydrogen, a halogen, a _{nitrile, CF 3, -Si (CH 3} ) 3, straight-chain or branched-chain alkyl of C1 ~ C5, C1 ~ C5 Straight or branched chain alkoxy; -N (C ₆ H ₅ ) ₂ or a carbazole-substituted or unsubstituted Phenyl; Pyridinyl, and -N (C ₆ H ₅ ) ₂ , or a substituted or unsubstituted
Phenyl, pyridinyl, triazinyl, naphthyl, 9,9-dimethyl fluorenyl flow carbonyl, dibenzo-furanyl, dibenzothiophene, carbazole and the sol or _{-N (C 6 H 5) 2} ,
At least one carbon atom, a nitrogen atom, an oxygen atom or a sulfur atom of Ar5 and N adjacent to Ar5 may be substituted or unsubstituted with at least one member selected from the group consisting of C1 to C5 linear or branched alkyl and phenyl groups A 5-membered ring or a 6-membered ring and may be fused to a ring containing X, and the 5-membered or 6-membered ring may further include at least one heteroatom selected from an oxygen atom, a nitrogen atom and a sulfur atom,
Ar 1 and Ar 5, Ar 3 and Ar 4, and Ar 6 and Ar 7 are each independently connected to form a 5-membered ring which is substituted or unsubstituted with at least one member selected from the group consisting of C 1 to C 5 linear or branched alkyl and phenyl groups Or a 6-membered ring, and the 5-membered or 6-membered ring may contain one or more hetero atoms selected from an oxygen atom, a nitrogen atom and a sulfur atom;
Wherein L2 or Z and Ar3 may be connected to form a 5-membered ring or a 6-membered ring which is substituted or unsubstituted with at least one member selected from the group consisting of C1-C5 straight-chain or branched-chain alkyl and phenyl groups, Or the 6-membered ring may contain one or more hetero atoms selected from an oxygen atom, a nitrogen atom and a sulfur atom;
Wherein R4 is hydrogen or -N (C ₆ H _{5) 2} group;
R5, R6, R7 and R8 are each independently hydrogen or a linear or branched alkyl group having from 1 to 5 carbon atoms,
In the above formulas (4) and (5)
At least one carbon atom, a nitrogen atom, an oxygen atom, or a sulfur atom of Ar6 and N adjacent to Ar6 are taken together with at least one substituent selected from the group consisting of C1 to C5 linear or branched alkyl and phenyl groups, A 5-membered ring or a 6-membered ring to which the N adjacent to Ar &lt; 6 &gt; may be fused to the phenylene ring,
In Formula 5,
At least one carbon atom, a nitrogen atom, an oxygen atom or a sulfur atom of Ar3 and N adjacent to Ar3 are taken together with at least one group selected from the group consisting of C1 to C5 linear or branched alkyl and phenyl groups, A 5-membered or 6-membered ring which may be fused to a phenylene ring adjacent to Ar &
Organic electroluminescent compound.
The method of claim 3,
The organic electroluminescent compound is any one of the following compounds 1 to 300
Organic electroluminescent compound.

The method according to claim 1,
The organic electroluminescent compound is used as a phosphorescent green host material, a hole injecting layer material, a hole transporting layer material, an electron injecting layer material, or an electron transporting layer material in a material for an organic EL device
Organic electroluminescent compound.
The method according to claim 1,
The organic electroluminescent compound may be used as a phosphorescent green host material or a hole transport layer material
Organic electroluminescent compound.
An organic electroluminescent device in which an organic thin film layer composed of one layer or a plurality of layers including at least a light emitting layer is sandwiched between a cathode and an anode,
Wherein at least one of the organic thin film layers contains the organic electroluminescent compound according to any one of claims 1 to 6 as a single species or a combination of two or more species.
8. The method of claim 7,
The organic thin film layer is formed by a solution process using the organic electroluminescent compound
Organic electroluminescent device.
8. The method of claim 7,
Wherein the organic electroluminescent compound is contained as at least one of a phosphorescent green host material, a hole injection layer material, a hole transport layer material, an electron injection layer material and an electron transport layer material
Organic electroluminescent device.
8. The method of claim 7,
Wherein the organic electroluminescent device has a structure in which an anode, a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, an electron injecting layer and a cathode are stacked in this order
Organic electroluminescent device.
An electronic device comprising the organic electroluminescent device according to claim 7.
12. The method of claim 11,
The electronic device may be an organic integrated circuit (O-IC), an organic field effect transistor (O-FET), an organic thin film transistor (O-TFT), an organic light emitting transistor (O- (O-FQD), a luminescent electrochemical cell (LEC), an organic laser diode (O-laser) or an organic light emitting device (OLED), which are organic photodetectors, organic photoreceptors,
Electronics.