KR20160123508A - An electroluminescent compound and an electroluminescent device comprising the same - Google Patents

Abstract

The present invention relates to an organic light emitting compound represented by chemical formula I or chemical formula II and, more specifically, to an anthracene derivative compound capable of driving at low voltage and implementing a device having significantly improved lifespan properties, and an organic light emitting device comprising the same.

Description

TECHNICAL FIELD The present invention relates to an organic electroluminescent compound and an organic electroluminescent device comprising the same,

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an organic light emitting compound, and more particularly, to an anthracene derivative compound capable of being driven at a low voltage and having a remarkably improved life characteristic, and an organic light emitting device including the same.

Materials used for an organic material layer in an organic light emitting device can be classified into a light emitting material and a charge transporting material, a hole injecting material, a hole transporting material, an electron transporting material, and an electron injecting material depending on functions. The light emitting material may be classified into a polymer type and a low molecular type depending on the molecular weight, and may be classified into a fluorescent material derived from singlet excited state of electrons and a phosphorescent material derived from the triplet excited state of electrons . Further, in the case of a light emitting material, it can be classified into blue, green and red light emitting materials and yellow and orange light emitting materials necessary for realizing a better natural color depending on a luminescent color.

On the other hand, when only one material is used as a light emitting material, there arises a problem that the maximum light emission wavelength shifts to a long wavelength due to intermolecular interaction, the color purity decreases, or the efficiency of the device decreases due to the light emission attenuating effect. A host-dopant system is used as a light-emitting material.

When the dopant having a smaller energy band gap than the host forming the light emitting layer is mixed with a small amount of the light emitting layer, the excitons generated in the light emitting layer are transported to the dopant to emit light with high efficiency. At this time, since the wavelength of the host is shifted to the wavelength band of the dopant, the light of the desired wavelength can be obtained according to the type of the dopant used.

However, development of a stable and efficient luminescent layer material has not been sufficiently accomplished, and development of new materials has been continuously required.

Japanese Patent Application Laid-Open No. 2005-041843 discloses a device using a phenanthryl anthracene derivative compound as a blue light emitting host material. However, since the device needs to be improved in driving voltage, it is difficult to commercialize it in a display device, 1999-003782 discloses a device using a host compound in which an anthracene ring and a naphthyl ring are directly bonded, but it is difficult to commercialize the device because of the problem that the lifetime characteristics of the device need to be improved.

In addition, various compounds having a naphthyl group, a phenyl group, and the like bonded to anthracene 9 and 10 at various positions are reported to be used as a blue light emitting material, but they still have problems in device driving voltage and long life.

Accordingly, it is an object of the present invention to provide an organic light emitting compound capable of driving a device at a low voltage and improving lifetime characteristics, and an organic light emitting device including the same.

In order to solve the above problems, the present invention provides an organic light emitting compound represented by the following general formula (I) or (II) and an organic light emitting device comprising the same in a light emitting layer.

(I) ≪ RTI ID = 0.0 &

The structure and specific substituents of the above formula (I) or (II) will be described later.

The organic luminescent device employing the anthracene derivative compound according to the present invention as a host compound in the luminescent layer can be advantageously used in various display and lighting industries by improving the low driving voltage and long life characteristics compared with the device using various anthracene derivatives have.

1 is a cross-sectional view illustrating a structure of an organic light emitting diode according to an exemplary embodiment of the present invention.

Hereinafter, the present invention will be described more specifically.

The present invention is an organic luminescent compound represented by the following formula (I) or (II), which is employed as a host compound in a luminescent layer in an organic luminescent device to further improve lifetime characteristics of the device.

(I) ≪ RTI ID = 0.0 &

In the above formula (I) or formula (II)

X, Y and Z are the same or different from each other and each independently selected from a single bond, a substituted or unsubstituted aromatic aryl group having 5 to 50 carbon atoms, and a substituted or unsubstituted heteroaryl group having 3 to 50 carbon atoms.

A and B are the same or different and each independently represents a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 carbon atoms.

R ₁ is selected from the group consisting of deuterium, a cyano group, a halogen group, a substituted or unsubstituted alkyl group having 1 to 24 carbon atoms, a substituted or unsubstituted halogenated alkyl group having 1 to 24 carbon atoms, a substituted or unsubstituted aryl group having 6 to 24 carbon atoms, A substituted or unsubstituted arylalkyl group having 6 to 24 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 24 carbon atoms, a substituted or unsubstituted heteroarylalkyl group having 2 to 24 carbon atoms, a substituted or unsubstituted arylcarbonyl group having 1 to 24 carbon atoms A substituted or unsubstituted alkylsilyl group having 1 to 24 carbon atoms, a substituted or unsubstituted arylsilyl group having 1 to 24 carbon atoms, and a substituted or unsubstituted aryloxy group having 1 to 24 carbon atoms (n is an integer of 0 to 8, and when n is 2 or more, plural R _{1 s} are the same or different from each other).

R ₂ And R ₃ are the same or different from each other and each independently selected from the group consisting of deuterium, a substituted or unsubstituted alkyl group having 1 to 24 carbon atoms, a substituted or unsubstituted halogenated alkyl group having 1 to 24 carbon atoms, a substituted or unsubstituted group having 6 to 24 A substituted or unsubstituted arylalkyl group having 6 to 24 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 24 carbon atoms, and a substituted or unsubstituted heteroarylalkyl group having 2 to 24 carbon atoms .

Wherein at least one of A, B, X, Y, Z and R ₁ to R ₃ is substituted with at least one deuterium.

The A and B are the same or different from each other and are each independently any one selected from among [Structural Formula 1] to [Structural Formula 9].

[Structural formula 1] [Structural formula 2] [Structural Formula 3]

[Structural Formula 4] [Structural Formula 5] [Structural Formula 6]

[Structural Formula 7] [Structural formula 8] [Structural Formula 9]

In the above Structural Formulas 1 to 9,

"- *" means that a 5-membered ring condensation ring containing N in the above formula (I) or (II) is formed while the aromatic hydrocarbon rings of the above-mentioned Structural Formulas 1 to 9 correspond to A rings and B rings ≪ / RTI >

R is as defined the above R _1. (M is an integer from 1 to 8, also a plurality of R is same or different when m is 2 or more)

In the formula (I) or (II), Y is a single bond, and Z is a substituent represented by the following structural formula (10).

[Structural Formula 10]

In the above structural formula 10,

R ₂₁ To R ₂₅ are the same as or different from each other and are the same as defined in the above R ₁ and may form a saturated or unsaturated ring by bonding with neighboring substituents.

On the other hand, X, Y, Z, A, B and R < ₁ > To R < ₃ > may each be independently substituted with one or more substituents, and the one or more substituents may be deuterium, cyano, halogen, hydroxy, nitro, An alkenyl group having 1 to 24 carbon atoms, an alkynyl group having 1 to 24 carbon atoms, a heteroalkyl group having 1 to 24 carbon atoms, an aryl group having 6 to 24 carbon atoms, an arylalkyl group having 6 to 24 carbon atoms, a heteroaryl group having 2 to 24 carbon atoms An alkyl group having 1 to 24 carbon atoms, an arylamino group having 1 to 24 carbon atoms, a heteroarylamino group having 1 to 24 carbon atoms, an alkyl group having 1 to 24 carbon atoms A silyl group, an arylsilyl group having 1 to 24 carbon atoms, and an aryloxy group having 1 to 24 carbon atoms.

Specific examples of the alkyl group used in the present invention include a methyl group, an ethyl group, a propyl group, an isopropyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, , An octyl group, a stearyl group, a trichloromethyl group, and a trifluoromethyl group, and at least one hydrogen atom of the alkyl group may be substituted with a substituent selected from the group consisting of a deuterium atom, a halogen atom, a hydroxyl group, a nitro group, a cyano group, a trifluoromethyl group, (in this case, "alkylsilyl group" hereinafter), a substituted or unsubstituted amino group (-NH _2, -NH (R), -N (R ') (R "), where R, R' and R" are each A hydrazine group, a hydrazone group, a carboxyl group, a sulfonic acid group, a phosphoric acid group, an alkyl group having 1 to 24 carbon atoms, an alkyl group having 1 to 24 carbon atoms (preferably an alkyl group having 1 to 24 carbon atoms) A halogenated alkyl group, an alkenyl group having 2 to 24 carbon atoms, an alkynyl group having 2 to 24 carbon atoms , Which it may be substituted with a heteroarylalkyl group having 1 to 24 carbon atoms heteroaryl group, having 5 to 24 aryl group, C 6 -C 24 aryl group, a C 3 -C 24 heteroaryl group, or having from 3 to 24 of the.

Specific examples of the alkoxy group used in the present invention include a methoxy group, an ethoxy group, a propoxy group, an isobutyloxy group, a sec-butyloxy group, a pentyloxy group, an isoamyloxy group and a hexyloxy group , The same substituent as in the case of the above-mentioned alkyl group can be substituted.

Specific examples of the halogen group used in the present invention include fluorine (F), chlorine (Cl), bromine (Br) and the like.

The aryloxy group used in the present invention means an -O-aryl radical, wherein the aryl group is as defined above, and specific examples include phenoxy, naphthoxy, anthracenyloxy, phenanthrenyloxy, fluorenyloxy, Indenyloxy and the like, and at least one hydrogen atom contained in the aryloxy group may be further substituted.

Specific examples of the silyl group used in the present invention include trimethylsilyl, triethylsilyl, triphenylsilyl, trimethoxysilyl, dimethoxyphenylsilyl, diphenylmethylsilyl, silyl, diphenylvinylsilyl, methylcyclobutylsilyl, dimethyl Furylsilyl and the like.

The aryl group used in the present invention is an organic radical derived from an aromatic hydrocarbon by one hydrogen elimination, and includes a single or fused ring system containing 5 to 7, preferably 5 or 6, Where a substituent is present, it can be fused with neighboring substituents to further form a ring.

Specific examples of the aryl group include a phenyl group, o-biphenyl group, m-biphenyl group, p-biphenyl group, o-terphenyl group, m-terphenyl group, p-terphenyl group, naphthyl group, anthryl group, , Aromatic groups such as a pyrenyl group, an indenyl group, a fluorenyl group, a tetrahydronaphthyl group, a perylene group, a crycenyl group, a naphthacenyl group and a fluoranthenyl group.

More specifically, at least one hydrogen atom of the aryl group may be substituted with at least one substituent selected from the group consisting of a deuterium atom, a halogen atom, a hydroxy group, a nitro group, a cyano group, a silyl group, an amino group (-NH ₂ , -NH (R), -N (R ') (R "), R' and R" are independently of each other an alkyl group having 1 to 10 carbon atoms and in this case an "alkylamino group"), an amidino group, An alkyl group having 1 to 24 carbon atoms, a halogenated alkyl group having 1 to 24 carbon atoms, an alkenyl group having 1 to 24 carbon atoms, an alkynyl group having 1 to 24 carbon atoms, a heteroatom having 1 to 24 carbon atoms, An alkyl group having 6 to 24 carbon atoms, an aryl group having 6 to 24 carbon atoms, an arylalkyl group having 6 to 24 carbon atoms, a heteroaryl group having 2 to 24 carbon atoms, a heteroarylalkyl group having 2 to 24 carbon atoms,

The heteroaryl group used in the present invention may be any one selected from the following structural formulas 11 to 20:

[Structural Formula 11] [Structural Formula 12] [Structural Formula 13] [Structural Formula 14]

[Structural Formula 15] [Structural Formula 16] [Structural Formula 17]

[Structural Formula 18] [Structural Formula 19] [Structural Formula 20]

In the above Structural Formulas 11 to 20,

T ₁ to T ₁₂ are the same or different and each independently represent C (R ₄₁ ), C (R ₄₂ ) (R ₄₃ ), N, N (R ₄₄ ), O, S, R ₄₅ ) (R ₄₆ ) and Ge (R ₄₇ ) (R ₄₈ ), and T ₁ to T ₁₂ may not all be carbon atoms at the same time, and R ₄₁ to R ₄₈ may be the same A substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C1-C30 aryl group, and a substituted or unsubstituted C1- Or a heteroaryl group having 2 to 30 carbon atoms with unsubstituted and hetero atoms O, N, S, or P;

The above-mentioned [formula 13] may contain a compound represented by the following formula [13] by a resonance structure resulting from the transfer of electrons.

[Structural Formula 13-1]

In the above Structural Formula 13-1, T ₁ to T ₇ are the same as defined in Structural Formula 11 to Structural Formula 20 above.

According to a preferred embodiment of the present invention, the above-mentioned structural formulas 11 to 20 can be selected from the following structural formula [21].

[Structural Formula 21]

In the above formula 21,

X is R < ₁ > in the formula [I] or [II] To as defined in R _3, and m is an integer from 1 to 11, when m is 2 or more, and a plurality of X are the same or different from each other, may be connected to the substituent of the above-mentioned [Chemical Formula I] or [formula II].

The organic luminescent compound represented by the above formula (I) or (II) may be any one selected from compounds represented by the following [compounds 1] to [48] The scope is not limited.

The present invention also provides an organic light emitting device comprising a first electrode, a second electrode, and an organic layer interposed between the first electrode and the second electrode, wherein the organic layer is represented by the formula (I) or (II) And an organic light-emitting compound.

The organic layer may be a single layer or a plurality of layers, and the organic layer may include a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, an electron injecting layer, a layer having both a hole injecting function and a hole transporting function, The layer may include at least one selected from the group consisting of

At this time, the organic layer may include a light emitting layer, and the light emitting layer is composed of a host and a dopant, and an organic light emitting compound according to the present invention may be used as a host compound of the light emitting layer.

In the present invention, various dopant compounds may be used in addition to the organic light emitting compound according to the present invention. When the light emitting layer includes a host and a dopant, the dopant content is generally about 100 parts by weight May be selected in a range of about 0.01 to about 20 parts by weight based on the weight of the composition.

The light emitting layer may further include an arylamine compound as a dopant compound in addition to the organic luminescent compound of the formula (I) or (II) according to the present invention. Specific examples thereof include compounds represented by the following formulas Can be displayed.

[Chemical Formula 1]

In the above formula (1)

X ₁ is a substituted or unsubstituted condensed aromatic group having 10 to 40 carbon atoms, Ar ₁ and Ar ₂ are the same or different and each independently represents a substituted or unsubstituted aromatic group having 6 to 40 carbon atoms, and n is 1 To (4), and when n is 2 or more, the plurality of (s) may be the same or different from each other.

(2)

In the above formula (2)

A is a substituted or unsubstituted condensed aromatic group having 10 to 40 carbon atoms, C _y is a substituted or unsubstituted cycloalkyl having 3 to 8 carbon atoms, b is an integer of 1 to 4, and when b is 2 or more May be the same or different from each other, and each cycloalkane may be in a fused form, and the hydrogen substituted on the C _y may be substituted with deuterium or an alkyl group, respectively.

B is a single bond or - [C (R ₄ ) (R ₅ )] _p -, p is an integer of 1 to 3, and when p is 2 or more, R ₄ and R ₅ are the same or different from each other .

R ₁ , R ₂ , R _{3 ,} R ₄ and R ₅ are each independently selected from the group consisting of hydrogen, deuterium, halogen atom, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine, hydrazone, A substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 60 carbon atoms, A substituted or unsubstituted C1-C60 alkoxy group, a substituted or unsubstituted C1-C60 alkylthio group, a substituted or unsubstituted C3-C60 cycloalkyl group, a substituted or unsubstituted C6-C60 Substituted or unsubstituted aryloxy groups having 5 to 60 carbon atoms, substituted or unsubstituted arylthio groups having 5 to 60 carbon atoms, substituted or unsubstituted heteroaryl groups having 2 to 60 carbon atoms, substituted or unsubstituted Carbon number 1 (Substituted or unsubstituted C1 to C60 alkyl) amino group, di (substituted or unsubstituted C1 to C60 alkyl) amino group, (substituted or unsubstituted C6 to C60 aryl) amino group and di (substituted or unsubstituted C6 to C60 Aryl) amino group.

a is an integer of 1 to 4, and when a is 2 or more, at least 2 of R ₃ may be the same or different from each other, each R ₃ may be a fused form, n is an integer of 1 to 4, (2) may be the same or different from each other.

Hereinafter, an embodiment of the organic light emitting diode according to the present invention will be described in more detail with reference to FIG.

The organic light emitting device according to the present invention includes an anode 20, a hole transporting layer 40, an organic light emitting layer 50, an electron transporting layer 60, and a cathode 80 And may further include a hole injecting layer 30 and an electron injecting layer 70 as necessary. In addition, one or two intermediate layers may be further formed, and a hole blocking layer or electron blocking layer A blocking layer may be further formed, and an organic layer having various functions may be further included depending on the characteristics of the device.

Referring to FIG. 1, the organic light emitting device of the present invention and a method of manufacturing the same will be described below.

First, an anode electrode material is coated on the substrate 10 to form an anode 20. Here, as the substrate 10, a substrate used in a typical organic light emitting device is used, and an organic substrate or a transparent plastic substrate having excellent transparency, surface smoothness, ease of handling, and waterproofness is preferable. As the material for the anode electrode, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO ₂ ), zinc oxide (ZnO) and the like which are transparent and excellent in conductivity are used.

A hole injecting layer 30 is formed on the anode 20 by vacuum thermal deposition or spin coating. Subsequently, a hole transport layer 40 is formed by vacuum thermal deposition or spin coating on the hole transport layer 30 above the hole injection layer 30.

The material for the hole injection layer is not particularly limited as long as it is commonly used in the art. Specific examples thereof include 2-TNATA [4,4 ', 4 "-tris (2-naphthylphenyl-phenylamino) -triphenylamine] , NPD [N, N'-diphenyl-N, N'-bis (3-methylphenyl) -1,1'- biphenyl-4,4'-diamine], DNTPD [N, N'-diphenyl-N, N'-bis- [4- ] Can be used.

The material for the hole transport layer is not particularly limited as long as it is commonly used in the art and includes, for example, N, N'-bis (3-methylphenyl) -N, N'- -Biphenyl] -4,4'-diamine (TPD) or N, N'-di (naphthalene-1-yl) -N, N'-diphenylbenzidine (? -NPD).

A hole blocking layer (not shown) is selectively formed on the organic light emitting layer 50 by a vacuum deposition method or a spin coating method to form a thin film on the organic light emitting layer 50 can do. In the case where holes are injected into the cathode through the organic light-emitting layer, the lifetime and the efficiency of the device are reduced, and thus the hole blocking layer plays a role of preventing such a problem by using a material having a very low HOMO (Highest Occupied Molecular Orbital) level . In this case, the hole blocking material to be used is not particularly limited, but it is required to have an ionization potential higher than that of the light emitting compound while having electron transporting ability. Typically, BAlq, BCP, TPBI and the like can be used.

Wherein a material used for the hole blocking layer, BAlq, BCP, Bphen, TPBI, NTAZ, BeBq _2, OXD-7, Liq and [Formula 501] to [Chemical Formula 507] either, but one that can be used is selected from, this limited It is not.

BAlq BCP Bphen

TPBI NTAZ BeBq ₂

OXD-7 Liq

(501) [502] ≪ EMI ID =

≪ EMI ID = ≪ EMI ID = ≪ EMI ID =

≪ EMI ID =

After the electron transport layer 60 is deposited on the hole blocking layer by a vacuum deposition method or a spin coating method, an electron injection layer 70 is formed, and a cathode forming metal is deposited on the electron injection layer 70 in a vacuum heat- And the cathode 80 is formed by vapor deposition to complete the organic EL device. Here, as the metal for forming the cathode, lithium, magnesium, aluminum, aluminum-lithium, calcium, magnesium-magnesium, Mg-Ag), and a transmissive cathode using ITO or IZO can be used to obtain a top light-emitting device.

As the electron transporting layer material, a known electron transporting material can be used as a material that stably transports electrons injected from an electron injection electrode (cathode). Examples of known electron transporting materials include quinoline derivatives, especially tris (8-quinolinolate) aluminum (Alq3), TAZ, Balq, beryllium bis (benzoquinolin-10- materials such as olate: Bebq2), ADN, [Formula 401], [Formula 402], and oxadiazole derivatives PBD, BMD, BND and the like may be used.

TAZ BAlq

[Compound 401] [Compound 402] BCP

Further, the electron transporting layer used in the present invention can be used as the organometallic compound represented by the following formula (C) alone or in combination with the electron transporting layer material.

≪ RTI ID = 0.0 &

In the above formula (C)

Y is a moiety selected from C, N, O and S, which is directly bonded to M to form a single bond, and any moiety selected from C, N, O and S is a moiety coordinating to M And is a ligand chelated by coordination bond with the single bond. M is an alkali metal, an alkaline earth metal, an aluminum (Al), or a boron (B) atom.

OA is a monovalent ligand capable of single bond or coordination bond with M, O is oxygen, A is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 carbon atoms, Substituted or unsubstituted C2-C30 alkenyl, substituted or unsubstituted C2-C20 alkynyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C5-C30 cycloalkyl An alkenyl group, and a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms having a hetero atom O, N, or S.

When m is 1 or n = 0 when M is one metal selected from alkali metals and m is 1 or n = 1 when M is a metal selected from alkaline earth metals, or m = 2 and n = 0, and when M is boron or aluminum, m is any one of 1 to 3 and n is any of 0 to 2, and m + n = 3.

The 'substituted' in the 'substituted or unsubstituted' may be a substituent selected from the group consisting of deuterium, cyano, halogen, hydroxy, nitro, alkyl, alkoxy, alkylamino, arylamino, heteroarylamino, alkylsilyl, An aryl group, an aryl group, a heteroaryl group, germanium, phosphorus, and boron.

The Y may be the same or different and independently selected from the following formulas [C1] to [C39], but is not limited thereto.

[Structural formula C1] [Structural formula C2] [Structural formula C3]

[Structural formula C4] [Structural formula C5] [Structural formula C6]

[Structural formula C7] [Structural formula C8] [Structural formula C9] [Structural formula C10]

[Structural formula C11] [Structural formula C12] [Structural formula C13]

[Structural formula C14] [Structural formula C15] [Structural formula C16]

[Structural formula C17] [Structural formula C18] [Structural formula C19] [Structural formula C20]

[Structural formula C21] [Structural formula C22] [Structural formula C23]

[Structural formula C24] [Structural formula C25] [Structural formula C26]

[Structural formula C27] [Structural formula C28] [Structural formula C29] [Structural formula C30]

[Structural formula C31] [Structural formula C32] [Structural formula C33]

[Structural formula C34] [Structural formula C35] [Structural formula C36]

[Structural formula C37] [Structural formula C38] [Structural formula C39]

In the above Structural Formula C1 to Structural Formula C39,

R is the same or different and is each independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-30 alkyl, substituted or unsubstituted C6-30 aryl, A substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C2-C30 alkenyl group, a substituted or unsubstituted C1-C30 alkoxy group, A substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 30 carbon atoms, and a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms And may be connected to an adjacent substituent by alkylene or alkenylene to form a spiro ring or a fused ring.

L represents a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted group having 5 to 30 carbon atoms A substituted or unsubstituted cycloalkyl group having 5 to 30 carbon atoms, L is an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, an aryl group having 6 to 40 carbon atoms, an aryl group having 3 to 20 carbon atoms, A heteroaryl group, a cyano group, a halogen group, deuterium, and hydrogen, and may be connected to an adjacent substituent by an alkylene or an alkenylene to form a spiro ring or a fused ring.

At least one layer selected from the hole injecting layer, the hole transporting layer, the electron blocking layer, the light emitting layer, the hole blocking layer, the electron transporting layer and the electron injecting layer may be formed by a single molecular deposition method or a solution process, Means a method of forming a thin film by evaporating a material used as a material for forming each of the layers by heating or the like under a vacuum or a low pressure state and the solution process is used as a material for forming each of the layers Means a method of forming a thin film by a method such as ink jet printing, roll-to-roll coating, screen printing, spray coating, dip coating, spin coating and the like.

Further, the organic light emitting device according to the present invention can be used in a device selected from a flat panel display device, a flexible display device, a monochromatic or white flat panel illumination device, and a monochromatic or white flexible illumination device.

Claims (9)

An organic light-emitting compound represented by the following formula (I) or (II):
(I) < RTI ID = 0.0 > (II)

In the above formula (I) or formula (II)
X, Y and Z are the same or different and are each independently selected from a single bond, a substituted or unsubstituted aromatic aryl group having 5 to 50 carbon atoms and a substituted or unsubstituted heteroaryl group having 3 to 50 carbon atoms;
A and B are the same or different and each independently represents a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 carbon atoms;
R ₁ is selected from the group consisting of deuterium, a cyano group, a halogen group, a substituted or unsubstituted alkyl group having 1 to 24 carbon atoms, a substituted or unsubstituted halogenated alkyl group having 1 to 24 carbon atoms, a substituted or unsubstituted aryl group having 6 to 24 carbon atoms, A substituted or unsubstituted arylalkyl group having 6 to 24 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 24 carbon atoms, a substituted or unsubstituted heteroarylalkyl group having 2 to 24 carbon atoms, a substituted or unsubstituted arylcarbonyl group having 1 to 24 carbon atoms A substituted or unsubstituted alkylsilyl group having 1 to 24 carbon atoms, a substituted or unsubstituted arylsilyl group having 1 to 24 carbon atoms, and a substituted or unsubstituted aryloxy group having 1 to 24 carbon atoms. (n is an integer of 0 to 8, and when n is 2 or more, plural R ₁ are the same or different from each other);
R ₂ And R ₃ are the same or different from each other and each independently selected from the group consisting of deuterium, a substituted or unsubstituted alkyl group having 1 to 24 carbon atoms, a substituted or unsubstituted halogenated alkyl group having 1 to 24 carbon atoms, a substituted or unsubstituted group having 6 to 24 A substituted or unsubstituted arylalkyl group having 6 to 24 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 24 carbon atoms, and a substituted or unsubstituted heteroarylalkyl group having 2 to 24 carbon atoms. ;
Wherein A, B, X, Y, Z and R ₁ to R ₃ are each independently a heavy hydrogen, a cyano group, a halogen group, a hydroxyl group, a nitro group, an alkyl group having 1 to 24 carbon atoms, a halogenated alkyl group having 1 to 24 carbon atoms, An alkenyl group having 1 to 24 carbon atoms, an alkynyl group having 1 to 24 carbon atoms, a heteroalkyl group having 1 to 24 carbon atoms, an aryl group having 6 to 24 carbon atoms, an arylalkyl group having 6 to 24 carbon atoms, a heteroaryl group having 2 to 24 carbon atoms, An alkoxy group having 1 to 24 carbon atoms, an alkylamino group having 1 to 24 carbon atoms, an arylamino group having 1 to 24 carbon atoms, a heteroarylamino group having 1 to 24 carbon atoms, an alkylsilyl group having 1 to 24 carbon atoms, An arylsilyl group having 1 to 24 carbon atoms and an aryloxy group having 1 to 24 carbon atoms;
Wherein at least one of A, B, X, Y, Z and R ₁ to R ₃ is substituted with at least one deuterium. The method according to claim 1,
Wherein A and B are the same as or different from each other and each independently selected from among [Structural Formula 1] to [Structural Formula 9].
[Structural formula 1] [Structural formula 2] [Structural formula 3]

[Structural formula 4] [Structural formula 5] [Structural formula 6]

[Structural formula 7] [Structural formula 8] [Structural formula 9]

In the above Structural Formulas 1 to 9,
"- *" means that a 5-membered ring condensation ring containing N in the above formula (I) or (II) is formed while the aromatic hydrocarbon rings of the above-mentioned Structural Formulas 1 to 9 correspond to A rings and B rings , ≪ / RTI >
R is as defined the above R _1. (M is an integer from 1 to 8, also a plurality of R is same or different when m is 2 or more) The method according to claim 1,
Wherein Y is a single bond, and Z is a substituent represented by the following structural formula (10): < EMI ID =
[Structural Formula 10]

In the above structural formula 10,
R ₂₁ To R ₂₅ are the same as or different from each other and are the same as defined in the above R ₁ and may form a saturated or unsaturated ring by bonding with neighboring substituents. The method according to claim 1,
The organic electroluminescent compound represented by the formula (I) or (II) is a compound selected from the following compounds [1] to [48]:

An organic light emitting device comprising a first electrode, a second electrode, and an organic layer interposed between the first electrode and the second electrode,
Wherein the organic layer comprises an organic light-emitting compound represented by Formula (I) or Formula (II) according to Claim 1: 6. The method of claim 5,
The organic layer may be a single layer or a plurality of layers, and the organic layer may include a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, an electron injecting layer, a layer having both a hole injecting function and a hole transporting function, Wherein the organic layer comprises at least one selected from the group consisting of a metal oxide and a metal oxide. The method of claim 6, wherein
Wherein the organic light emitting compound represented by Formula (I) or Formula (II) is contained in the light emitting layer. 8. The method of claim 7,
Wherein the light emitting layer further comprises an arylamine compound. 6. The method of claim 5,
Wherein the organic light emitting device comprises one or more light emitting layers emitting blue, red or green light to emit white light.

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