KR102139781B1 - An organoelectro luminescent compounds and organoelectro luminescent device using the same - Google Patents

Abstract

The present invention relates to an organic light emitting device represented by the following [Chemical Formula I] to [Chemical Formula III] and an organic electroluminescent device comprising the same, wherein the organic electroluminescent device comprising the organic light emitting compound according to the present invention has luminance and luminous efficiency. It has excellent power efficiency while being able to drive low voltage while being excellent.
[Formula Ⅰ] [Formula Ⅱ] [Formula Ⅲ]

Description

An organoelectro luminescent compound and organoelectro luminescent device using the same}

The present invention relates to an organic light emitting compound and an organic electroluminescent device comprising the same.

Recently, the organic light emitting device capable of driving a low voltage as a self-emission type has superior viewing angle, contrast ratio, etc., and does not require a backlight, is lightweight and thin, is advantageous in terms of power consumption, and reproduces color compared to a liquid crystal display, which is a mainstream of flat panel display elements. The wide range has attracted attention as a next-generation display device.

An organic electroluminescent device is a device that emits light while extinguishing after pairing electrons and holes when a charge is injected into an organic light emitting layer formed between an electron injection electrode (cathode) and a hole injection electrode (anode).

The organic light emitting device can not only form the device on a transparent substrate that can be bent like plastic, but can also be driven at a voltage lower than 10 V compared to a plasma display panel or an inorganic electroluminescent display, and consumes less power. , Has the advantage of excellent color. In addition, the organic electroluminescent device can display three colors: green, blue, and red, and is a subject of great interest as a next-generation rich color display device.

The most important factor in determining the luminous efficiency in an organic light emitting device is a light emitting material. Fluorescent materials are currently widely used as luminescent materials, but the development of phosphorescent materials is one of the methods that can theoretically improve the luminous efficiency due to the luminescence mechanism, and accordingly, various phosphorescent materials have been developed to date. In particular, CBP (4,4'-N,N'-dicarbazolbiphenyl) is the most widely known phosphorescent host material, and substances introduced with various substituents on carbazole (Japanese Patent Publication 2008-214244, Japanese Patent Publication) 2003-133075) or an organic electroluminescent device using a BALq derivative as a host is known.

However, the organic light emitting device using a phosphorescent material has a significantly higher current efficiency than a device using a fluorescent material, but when using a material such as BAlq, CBP as a host for the phosphorescent material, it is driven compared to a device using a fluorescent material. Since the voltage is high, there is no great advantage in terms of power efficiency, and it is also not satisfactory in terms of the life of the device, and thus there is a need to develop a more stable and high-performance host material in driving voltage and life characteristics.

The present invention is to provide an organic light-emitting compound having improved power efficiency by being able to drive low voltage at the same time as being superior in luminance and emission efficiency than conventional materials.

In addition, the present invention is to provide a low-voltage driving by adopting the organic light emitting compound as a light emitting material to provide an improved power efficiency, high brightness, high efficiency organic electroluminescent device.

In order to solve the above problems, the present invention provides an organic light emitting compound represented by the following [Formula I] to [Formula III].

[Formula Ⅰ] [Formula Ⅱ] [Formula Ⅲ]

In addition, the present invention is composed of a first electrode, a second electrode opposed to the first electrode, and at least one organic layer interposed between the first electrode and the second electrode, and the organic layer is the above [Formula I] to An organic electroluminescent device comprising at least one organic light emitting compound represented by [Formula III] is provided.

Specific substituents of the organic light-emitting compounds represented by [Chemical Formula I] to [Chemical Formula III] according to the present invention will be described later.

When the organic light emitting compound according to the present invention is employed in an organic electroluminescent device, low voltage driving is possible, so that a device having excellent power efficiency and high brightness and high efficiency characteristics can be realized.

1 is a conceptual diagram showing the structure of an organic light emitting device according to an embodiment of the present invention.

Hereinafter, the present invention will be described in more detail.

The organic light emitting compound according to the present invention is characterized by being represented by the following [Formula I] to [Formula III].

[Formula Ⅰ] [Formula Ⅱ] [Formula Ⅲ]

In the above [Formula I] to [Formula III],

X ₁ to X ₈ may be the same as or different from each other, and each independently N or CR ₁₃ .

R ₁ to R ₁₃ may be the same or different from each other, and each independently hydrogen, deuterium, halogen group, cyano group, hydroxyl group, nitro group, substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted Alkenyl group having 2 to 30 carbon atoms, substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, substituted Or an unsubstituted cycloalkenyl group having 3 to 30 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl having 5 to 50 carbon atoms Oxy group, a substituted or unsubstituted alkylamino group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 30 carbon atoms. It is selected from the group consisting of a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms and a substituted or unsubstituted arylsilyl group having 5 to 50 carbon atoms.

L is a linking group, a single bond or a substituted or unsubstituted alkylene group having 1 to 30 carbon atoms, a substituted or unsubstituted carbon group having 2 to 30 carbon atoms Alkenylene group, a substituted or unsubstituted alkynylene group having 2 to 30 carbon atoms, a substituted or unsubstituted 3 to 30 carbon atoms Cycloalkylene group, a substituted or unsubstituted arylene group having 5 to 50 carbon atoms and a substituted or unsubstituted heteroarylene group having 2 to 50 carbon atoms.

In addition, n is an integer of 0 to 3, and when n is 2 or more, a plurality of Ls are the same or different from each other, and the Ls may combine with each other or adjacent substituents to form a saturated or unsaturated ring.

According to an embodiment of the present invention, R ₁ to R ₁₃ may be combined with each other or adjacent substituents to form an alicyclic, aromatic monocyclic or polycyclic ring. In addition, the carbon atom of the formed ring may be substituted with any one or more heteroatoms selected from N, S, O and P.

According to an embodiment of the present invention, the L and R ₁ to R ₁₃ are more specifically each independently hydrogen, deuterium, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted carbon number having 1 to 20 carbon atoms. Alkenyl group, a substituted or unsubstituted aryl group having 5 to 20 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 20 carbon atoms, a substituted or unsubstituted carbon number 6 to 20 arylsilyl group, an unsubstituted alkylamine group having 1 to 20 carbon atoms and a substituted or unsubstituted arylamine group having 6 to 20 carbon atoms, and n is a single bond, 1 or 2 It is characterized by.

According to an embodiment of the present invention, when n is 1, L may be any one of the following [Structural Formula A1] to [Structural Formula A8].

[Structural Formula A1] [Structural Formula A2] [Structural Formula A3] [Structural Formula A4]

[Structural Formula A5] [Structural Formula A6] [Structural Formula A7] [Structural Formula A8]

In [Structural Formula A1] to [Structural Formula A8], hydrogen or deuterium may be bonded to carbon of the aromatic ring in each structural formula.

According to another embodiment of the present invention, when n is 2, L may be any one of the linkers selected from the following [Structural Formula B].

[Structural Formula B]

In [Structural Formula B], hydrogen or deuterium may be bonded to carbon of the aromatic ring in each structural formula, and in the case of substituents other than hydrogen, adjacent substituents may be combined with each other to form a saturated or unsaturated ring.

The'substituted' in the'substituted or unsubstituted' is deuterium, cyano group, halogen group, hydroxy group, nitro group, alkyl group having 1 to 20 carbon atoms, alkenyl group having 1 to 20 carbon atoms, alkynyl group having 1 to 20 carbon atoms, Halogenated alkyl group having 1 to 20 carbon atoms, aryl group having 5 to 24 carbon atoms, heteroaryl group having 2 to 24 carbon atoms, alkoxy group having 1 to 20 carbon atoms, aryloxy group having 5 to 24 carbon atoms, alkylsilyl group having 1 to 20 carbon atoms , Which means that it is further substituted with one or more substituents selected from an arylsilyl group having 5 to 24 carbon atoms, an alkylamine group having 1 to 20 carbon atoms and an arylamine group having 6 to 24 carbon atoms, wherein R ₁ to R ₁₃ And L may be each independently further substituted by the above substituents.

In addition, the range of the carbon number of the alkyl group or the aryl group in the "substituted or unsubstituted alkyl group having 1 to 30 carbon atoms" or the "substituted or unsubstituted aryl group having 5 to 50 carbon atoms" is considered the portion where the substituent is substituted It does not mean the total number of carbon atoms constituting the alkyl portion or the aryl portion when viewed as unsubstituted. For example, the phenyl group substituted with a butyl group in the para position means that it corresponds to an aryl group having 6 carbon atoms substituted with a butyl group having 4 carbon atoms.

On the other hand, the aryl group, which is a substituent used in the present invention, is an organic radical derived from an aromatic hydrocarbon by one hydrogen removal, and includes a single or fused ring system containing 5 to 7 members, preferably 5 or 6 members, In addition, when there is a substituent in the aryl group, the adjacent substituents may be fused with each other to form a ring.

Specific examples of the aryl are phenyl group, 2-methylphenyl group, 3-methylphenyl group, 4-methylphenyl group, 4-ethylphenyl group, o-biphenyl group, m-biphenyl group, p-biphenyl group, 4-methylbiphenyl group, 4- Ethyl biphenyl group, o-terphenyl group, m-terphenyl group, p-terphenyl group, 1-naphthyl group, 2-naphthyl group, 1-methylnaphthyl group, 2-methylnaphthyl group, anthryl group, phenanthryl group, pyrene And aromatic groups such as nil group, indenyl, fluorenyl group, tetrahydronaphthyl group, pyrenyl, peryleneyl, chrysenyl, naphthacenyl, fluoranthenyl, and the like.

At least one hydrogen atom of the aryl group is a deuterium atom, a halogen atom, a hydroxyl group, a nitro group, a cyano group, a silyl group, an amino group (-NH ₂ , -NH(R), -N(R')(R"), R 'And R'are each independently an alkyl group having 1 to 10 carbon atoms, in this case referred to as an "alkylamino group"), amidino group, hydrazine group, hydrazone group, carboxyl group, sulfonic acid group, phosphoric acid group, alkyl group having 1 to 24 carbon atoms, Halogenated alkyl group having 1 to 24 carbon atoms, alkenyl group having 1 to 24 carbon atoms, alkynyl group having 1 to 24 carbon atoms, heteroalkyl group having 1 to 24 carbon atoms, aryl group having 6 to 24 carbon atoms, arylalkyl group having 6 to 24 carbon atoms, carbon number It may be substituted with a heteroaryl group having 2 to 24 or a heteroarylalkyl group having 2 to 24 carbon atoms.

The heteroaryl group which is a substituent used in the present invention may be any one selected from the following [Structural Formula 1] to [Structural Formula 6].

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

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

In the above [Structural Formula 1] to [Structural Formula 6],

T ₁ to T ₈ are the same as or different from each other, and each independently, C(R ₄₁ ), C(R ₄₂ )(R ₄₃ ), N, N(R ₄₄ ), may be any one selected from O and S, , R ₃₁ to R ₄₄ are the same or different from each other, and each independently hydrogen, deuterium, substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, substituted or unsubstituted It may be any one selected from an aryl group having 5 to 30 carbon atoms and a substituted or unsubstituted heteroaryl group having 2, 30 carbon atoms having O, NS, and P, and each of the above [Structural Formulas 1] to [Structural Formula] 6] to R ₃₁ to R ₄₄ One of the above may form a single bond with the substituent or nitrogen in [Formula I] to [Formula III].

In addition, [Structural Formula 3] may include a compound represented by the following [Structural Formula 3-1] due to a resonance structure according to the movement of electrons.

[Structural Formula 3-1]

In [Structural Formula 3-1], T ₁ to T ₅ and R ₃₃ and R ₃₄ are the same as defined above.

Further, according to a preferred embodiment of the present invention, the above [Structural Formula 1] to [Structural Formula 6] may be selected from the following [Structural Formula 7].

[Structural Formula 7]

In the above [Formula 7],

X is hydrogen, deuterium, substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted aryl group having 5 to 30 carbon atoms, substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, substituted or unsubstituted carbon number 2 to 20 alkynyl groups, substituted or unsubstituted cycloalkyl groups having 3 to 30 carbon atoms, substituted or unsubstituted cycloalkenyl groups having 5 to 30 carbon atoms, substituted or unsubstituted alkoxy groups having 1 to 30 carbon atoms, substituted or unsubstituted Aryloxy group having 6 to 30 carbon atoms, substituted or unsubstituted alkylthioxy group having 1 to 30 carbon atoms, substituted or unsubstituted arylthiooxy group having 5 to 30 carbon atoms, substituted or unsubstituted alkyl having 1 to 30 carbon atoms Group consisting of amine group, substituted or unsubstituted aryl group having 5 to 5 carbon atoms, substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms having O, N, S and P, cyano group, nitro group, halogen group Any one selected from, m is an integer of 1 to 11, and when m is 2 or more, a plurality of Xs are the same or different from each other, and any one of the one or more Xs is in the above [Formula I] to [Formula III]. A single bond with a substituent or nitrogen can be achieved.

Specific examples of the alkyl group which is a substituent used in the present invention are methyl group, ethyl group, propyl group, isopropyl group, isobutyl group, sec-butyl group, tert-butyl group, pentyl group, iso-amyl group, hexyl group, heptyl group , Octyl group, stearyl group, trichloromethyl group, trifluoromethyl group, and the like, and one or more hydrogen atoms among the alkyl groups include deuterium atom, halogen atom, hydroxy group, nitro group, cyano group, trifluoromethyl group, and silyl group. (In this case referred to as “alkylsilyl group”), a substituted or unsubstituted amino group (-NH ₂ , -NH(R), -N(R')(R"), wherein R, R'and R" are each Independently an alkyl group having 1 to 24 carbon atoms (in this case, referred to as an "alkylamino group"), an amidino group, 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, 1 to 24 carbon atoms Halogenated alkyl group, alkenyl group having 2 to 24 carbon atoms, alkynyl group having 2 to 24 carbon atoms, heteroalkyl group having 1 to 24 carbon atoms, aryl group having 5 to 24 carbon atoms, arylalkyl group having 6 to 24 carbon atoms, hetero group having 3 to 24 carbon atoms It may be substituted with an aryl group or a heteroaryl alkyl group having 3 to 24 carbon atoms.

Specific examples of the alkoxy group which is a substituent used in the present invention include methoxy group, ethoxy group, propoxy group, isobutyloxy group, sec-butyloxy group, pentyloxy group, iso-amyloxy group, hexyloxy group and the like. It can be substituted with the same substituents as in the case of the alkyl group.

Specific examples of the halogen group which is a substituent used in the compound of the present invention include fluorine (F), chlorine (Cl), and bromine (Br).

The aryloxy group, which is a substituent used in the present invention, means an -O- aryl radical, wherein the aryl group is as defined above, and as a specific example, phenoxy, naphthoxy, anthracenyloxy, phenanthrenyloxy, fluorenyl Oxy, indenyloxy, and the like, and one or more hydrogen atoms contained in the aryloxy group can be further substituted.

Specific examples of the silyl group which is a substituent used in the present invention include trimethylsilyl, triethylsilyl, triphenylsilyl, trimethoxysilyl, dimethoxyphenylsilyl, diphenylmethylsilyl, diphenylvinylsilyl, methylcyclobutylsilyl, dimethyl And furylsilyl.

Specific examples of the alkenyl group used in the present invention represent a straight or branched alkenyl group, 3-pentenyl group, 4-hexenyl group, 5-heptenyl group, 4-methyl-3-pentenyl group, 2,4 -Dimethyl-pentenyl group, 6-methyl-5-heptenyl group, 2,6-dimethyl-5-heptenyl group, etc. are mentioned.

The organic light emitting compounds represented by [Chemical Formula I] to [Chemical Formula III] according to the present invention may be more specifically selected from [Compound 1] to [Compound 15], but are not limited thereto.

[Compound 1] [Formula 2] [Formula 3]

[Compound 4] [Formula 5] [Formula 6]

[Compound 7] [Formula 8] [Formula 9]

[Compound 10] [Formula 11] [Formula 12]

[Compound 13] [Formula 14] [Formula 15]

In addition, the present invention includes a first electrode, a second electrode opposed to the first electrode, and an organic layer interposed between the first electrode and the second electrode, wherein the organic layer is the above Chemical Formula I in the present invention. It may include at least one organic light-emitting compound represented by [Chemical Formula III].

In addition, the organic layer containing the organic light emitting compound of the present invention may include at least one of a hole injection layer, a hole transport layer, a functional layer having a hole injection function and a hole transport function simultaneously, a light emitting layer, an electron transport layer, and an electron injection layer have. At this time, the organic layer interposed between the first electrode and the second electrode may include a light emitting layer, the light emitting layer is made of a host and a dopant, and the organic light emitting compound of the present invention can be used as a host.

Meanwhile, in the present invention, a dopant material may be used in addition to the host in the light emitting layer. When the light emitting layer includes a host and a dopant, the content of the dopant may be generally selected from about 0.01 to about 20 parts by weight based on about 100 parts by weight of the host.

Hereinafter, the organic electroluminescent device of the present invention will be described with reference to FIG. 1.

1 is a cross-sectional view showing the structure of an organic light emitting device of the present invention. The organic light emitting device according to the present invention includes an anode 20, a hole transport layer 40, an organic light emitting layer 50, an electron transport layer 60 and a cathode 80, and a hole injection layer 30, if necessary The electron injection layer 70 may be further included, and in addition, an intermediate layer of one or two layers may be further formed, and a hole blocking layer or an electron blocking layer may be further formed.

Referring to FIG. 1, an organic electroluminescent device of the present invention and a manufacturing method thereof are as follows.

First, an anode 20 is formed by coating a material for the anode electrode on the substrate 10. Here, as the substrate 10, a substrate used in a conventional organic EL device is used, but an organic substrate or a transparent plastic substrate having excellent transparency, surface smoothness, handling ease, and waterproofness is preferable. In addition, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO ₂ ), and zinc oxide (ZnO) are used as the anode electrode material, which is transparent and has excellent conductivity.

A hole injection layer 30 is formed by vacuum-evaporating or spin coating a hole injection layer material on the anode 20 electrode. Next, a hole transport layer 40 is formed by vacuum thermally evaporating or spin coating the hole transport layer material on the hole injection layer 30.

The hole injection layer material can be used without particular limitation as long as it is commonly used in the art, for example, 2-TNATA[4,4',4"-tris(2-naphthylphenyl-phenylamino)-triphenylamine] , NPD[N,N'-di(1-naphthyl)-N,N'-diphenylbenzidine)], TPD[N,N'-diphenyl-N,N'-bis(3-methylphenyl)-1,1'- biphenyl-4,4'-diamine], DNTPD[N,N'-diphenyl-N,N'-bis-[4-(phenyl-m-tolyl-amino)-phenyl]-biphenyl-4,4'-diamine ] Etc. can be used.

In addition, it is not particularly limited as long as it is commonly used in the art as a material for the hole transport layer, for example, N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1 -Biphenyl]-4,4'-diamine (TPD) or N,N'-di(naphthalen-1-yl)-N,N'-diphenylbenzidine (α-NPD) or the like can be used.

Subsequently, an organic light emitting layer 50 is stacked on the hole transport layer 40 and a hole blocking layer (not shown) is selectively deposited on the organic light emitting layer 50 to form a thin film as a vacuum deposition method or a spin coating method. can do. The hole blocking layer serves to prevent this problem by using a material with a very low level of HOMO (Highest Occupied Molecular Orbital) because the life and efficiency of the device is reduced when holes pass through the organic light emitting layer and enter the cathode. . At this time, the hole blocking material used is not particularly limited, but has an electron transporting ability and has a higher ionization potential than the light emitting compound, and typically BAlq, BCP, TPBI, etc. may be used.

As the material used for the hole blocking layer, any one selected from BAlq, BCP, Bphen, TPBI, NTAZ, BeBq ₂ , OXD-7, Liq and [Formula 101] to [Formula 107] may be used, but is not limited thereto. It does not work.

BAlq BCP Bphen

TPBI NTAZ BeBq ₂

OXD-7 Liq

Formula 101 Formula 102 Formula 103

Formula 104 Formula 105 Formula 106

Formula 107

After the electron transport layer 60 is deposited on the hole blocking layer through a vacuum deposition method or a spin coating method, an electron injection layer 70 is formed and a metal for forming a cathode is vacuum-coated on the electron injection layer 70. The organic EL device is completed by depositing to form the cathode 80 electrode. Here, the cathode forming metals include lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), and magnesium-silver ( Mg-Ag) and the like, and a transmissive cathode using ITO and IZO can be used to obtain a front light emitting device.

As the electron transport layer material, a known electron transport material may be used as a function of stably transporting electrons injected from the electron injection electrode (Cathode). Examples of known electron transport materials include quinoline derivatives, in particular tris(8-quinolinorate)aluminum (Alq3), TAZ, Balq, beryllium bis(benzoquinolin-10-noate) (beryllium bis (benzoquinolin-10- It is also possible to use materials such as olate: Bebq2), ADN, [Compound 201], [Compound 202], and oxadiazole derivatives PBD, BMD, BND.

TAZ BAlq

[Compound 201] [Compound 202] BCP

Further, in the electron transport layer used in the present invention, the organometallic compound represented by the following [Chemical Formula C] may be used alone or in combination with the electron transport layer material.

[Chemical Formula C]

In the above [Formula C],

Y is a portion selected from C, N, O, and S directly bonded to M to form a single bond, and a portion selected from C, N, O, and S forming a coordination bond to M. And a ligand chelated by the single bond and coordination bond.

M is an alkali metal, alkaline earth metal, aluminum (Al) or boron (B) atom.

OA is a monovalent ligand capable of single bond or coordination with the M, wherein O is oxygen, and 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 alkenyl group having 2 to 30 carbon atoms, substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, substituted or unsubstituted cycloalkyl having 5 to 30 carbon atoms It is any one selected from an alkenyl group and a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms having O, N or S as a hetero atom.

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

The'substituted' in the'substituted or unsubstituted' is deuterium, cyano group, halogen group, hydroxy group, nitro group, alkyl group, alkoxy group, alkylamino group, arylamino group, hetero arylamino group, alkylsilyl group, arylsilyl group, It means substituted with one or more substituents selected from the group consisting of aryloxy group, aryl group, heteroaryl group, germanium, phosphorus and boron.

In addition, each of Y is the same or different, and may be any one selected from the following [Structural C1] to [Structural C39] independently of each other.

[Structural Formula C1] [Structural Formula C2] [Structural Formula C3]

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

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

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

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

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

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

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

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

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

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

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

In the above [Structural Formula C1] to [Structural Formula C39],

R are the same or different from each other, and each independently hydrogen, deuterium, halogen, cyano group, substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted aryl group having 6 to 30 carbon atoms, substituted or unsubstituted Heteroaryl group having 3 to 30 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, substituted or Unsubstituted alkylamino group having 1 to 30 carbon atoms, substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, substituted or unsubstituted arylamino group having 6 to 30 carbon atoms, and substituted or unsubstituted arylsilyl having 6 to 30 carbon atoms. It is selected from groups, and may be connected to adjacent substituents with alkylene or alkenylene to form a spiro ring or fused ring.

L is 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 5 to 30 carbon atoms Heteroaryl group and 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, 3 to 20 carbon atoms It is further substituted with one or more substituents selected from heteroaryl groups, cyano groups, halogen groups, deuterium, and hydrogen, and may be connected to adjacent substituents with alkylene or alkenylene to form a spiro ring or fused ring.

The organic electroluminescent device according to the present invention is characterized in that the organic layer includes a light emitting layer, and the light emitting layer further comprises at least one phosphorescent dopant in addition to at least one organic light emitting compound represented by [Formula I] to [Formula III]. And, the light emitting dopant applied to the organic electroluminescent device of the present invention is not particularly limited, but may be one or more compounds selected from compounds represented by the following [General Formula A-1] to [General Formula J-1]. have.

[Formula A-1]

ML ₁ L ₂ L ₃

The M is selected from the group consisting of metals of Groups 7, 8, 9, 10, 11, 13, 14, 15, and 16, preferably Ir, Pt, Pd, Rh, Re , Os, Tl, Pb, Bi, In, Sn, Sb, Te, Au and Ag. In addition, the L ₁ , L ₂ and L ₃ are the same as or different from each other as a ligand, and each independently selected from the following [Structural Formula D], but is not limited thereto.

In addition, * in the following structural formula D represents a site coordinated to the metal ion M.

[Structural Formula D]

In the above [Formula D],

R is different from or the same as each other, and each independently hydrogen, deuterium, halogen, cyano group, substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted aryl group having 6 to 50 carbon atoms, substituted or unsubstituted Heteroaryl group having 5 to 50 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, substituted or Unsubstituted alkylamino group having 1 to 30 carbon atoms, substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, substituted or unsubstituted arylamino group having 6 to 30 carbon atoms and substituted or unsubstituted arylsilyl having 6 to 30 carbon atoms It may be any one selected from groups.

Each R is independently selected from alkyl groups having 1 to 20 carbon atoms, cycloalkyl groups having 3 to 20 carbon atoms, aryl groups having 6 to 40 carbon atoms, heteroaryl groups having 3 to 20 carbon atoms, cyano groups, halogen groups, deuterium, and hydrogen. It may be further substituted with one or more substituents.

In addition, R may be connected to each adjacent substituent by alkylene or alkenylene to form an alicyclic ring and a monocyclic or polycyclic aromatic ring.

The L may be connected to an adjacent substituent by alkylene or alkenylene to form a spiro ring or fused ring.

As an example, the dopant represented by [General Formula A-1] may be any one selected from the following compounds.

[General Formula B-1]

In the above [General Formula B-1],

M ^A1 represents the same metal ion as defined in [General Formula A-1], and Y ^A11 , Y ^A14 , Y ^A15 and Y ^A18 Each independently represents a carbon atom or a nitrogen atom, Y ^A12 , Y ^A13 , Y ^A16 and Y ^A17 each independently represent a substituted or unsubstituted carbon atom, a substituted or unsubstituted nitrogen atom, an oxygen atom, and a sulfur atom, L ^A11 , L ^A12 , L ^A13 , and L ^A14 each represent a linking group as previously defined, and Q ^A11 , Q ^A12 represent a partial structure containing an atom that binds to M ^A1 .

The exemplary structure of the compound represented by [General Formula B-1] is as follows, but is not limited thereto.

[General Formula C-1]

In the above [General Formula C-1],

M ^B1 represents the same metal ion as defined in [General Formula A-1], Y ^B11 , Y ^B14 , Y ^B15 and Y ^B18 each independently represent a carbon atom or a nitrogen atom, Y ^B12 , Y ^B13 , Y ^B16 And Y ^B17 each independently represents a substituted or unsubstituted carbon atom, a substituted or unsubstituted nitrogen atom, an oxygen atom, and a sulfur atom, and L ^B11 , L ^B12 , L ^B13 , and L ^B14 represent a linking group, and Q ^B11 , Q ^B12 represents a partial structure containing an atom that binds M ^B1 .

The exemplary structure of the compound represented by [General Formula C-1] is as follows, but is not limited thereto.

[General formula D-1]

In the above [General Formula D-1],

M ^C1 represents a metal ion as the same metal ion as defined in [General Formula A-1], and R ^C11 and R ^C12 are each independently a hydrogen atom, a substituent that connects to each other, and forms a five-membered ring, without any connection to each other. Represents a substituent, R ^C13 , R ^C14 each independently represents a hydrogen atom, a substituent that connects to each other to form a 5-membered ring, or a substituent that does not have anything to connect to each other, G ^C11 , G ^C12 each independently represents a nitrogen atom, a substitution Or represents an unsubstituted carbon atom, L ^C11 , L ^C12 represents a linking group, and Q ^C11 , Q ^C12 represents a partial structure containing an atom bound to M ^C1 .

The exemplary structure of the compound represented by [General Formula D-1] is as follows, but is not limited thereto.

[General Formula E-1]

In the above [General Formula E-1],

M ^D1 represents the same metal ion as defined in [General Formula A-1], G ^D11 and G ^D12 each independently represent a nitrogen atom, a substituted or unsubstituted carbon atom, and J ^D11 , J ^D12 , J ^D13 and J ^D14 represents a group of atoms required to form a 5-membered ring independently of each other, and L ^D11 and L ^D12 represent a linking group.

The exemplary structure of the compound represented by [General Formula E-1] is as follows, but is not limited thereto.

[General Formula F-1]

In the above [General Formula F-1],

M ^E1 represents the same metal ion as defined in [General Formula A-1], and J ^E11 and J ^E12 each independently represent a group of atoms required to form a 5-membered ring, G ^E11 , G ^E12 , G ^E13 and G ^E14 each independently represents a nitrogen atom, a substituted or unsubstituted carbon atom, and Y ^E11 , Y ^E12 , Y ^E13 and Y ^E14 each independently represent a nitrogen atom, a substituted or unsubstituted carbon atom.

The exemplary structure of the compound represented by [General Formula F-1] is as follows, but is not limited thereto.

[General formula G-1]

In the above [General Formula G-1],

M ^F1 represents the same metal ion as defined in [General Formula A-1].

L ^F11 , L ^F12 and L ^F13 represent a linking group, R ^F11 , R ^F12 , R ^F13 and R ^F14 represent a substituent, R ^F11 and R ^F12 , R ^F12 And R ^F13 , R ^F13 and R ^F14 may be connected to each other to form a ring, wherein the rings formed by R ^F1 and R ^F12 , R ^F13 and R ^F14 are 5-membered rings. In addition, Q ^F11 and Q ^F12 represent partial structures containing atoms that bind to M ^F1 .

The exemplary structure of the compound represented by [General Formula G-1] is as follows, but is not limited thereto.

[General Formula H-1] [General Formula H-2] [General Formula H-3]

In the above [General Formula H-1],

R ¹¹ , R ¹² are alkyl, aryl or heteroaryl substituents; In addition, it is possible to form a fused ring with a substituent adjacent to each other, q11, q12 is an integer of 0 to 4, preferably 0 to 2.

In addition, when q11 and q12 are 2 to 4, a plurality of R11 and R12 may be the same or different, respectively.

L ¹ is a ligand that binds to platinum, and is preferably a ligand capable of forming an ortho metalized platinum complex, a nitrogen-containing heterocyclic ligand, a diketone ligand, or a halogen ligand, and more preferably an ortho metal. A ligand forming a platinum complex), a bipyridyl ligand, or a phenanthroline ligand.

n ¹ is an integer from 0 to 3, preferably 0, m ¹ is 1 or 2, and preferably 2.

Moreover, it is preferable that n ¹ and m ¹ are such that the metal complex represented by the general formula H-1 is a neutral complex.

In the general formula H-2, R ²¹ , R ²² , n ² , m ² , q ²² , L ² are respectively the same as R ¹¹ , R ¹² , n ¹ , m ¹ , q ¹² , L ¹ , q ²¹ is an integer of 0-2, and 0 is preferable.

In the general formula H-3, R ³¹ , n ³ , m ³ , L ³ are respectively the same as R ¹¹ , n ¹ , m ¹ , L ^1, and q ³¹ represents an integer from 0 to 8, and 0 to 2 is preferable, and 0 is more preferable.

Examples of specific compounds of the general formulas H-1 to H-3 are as follows, but are not limited thereto.

[General Formula I-1]

In the above [General Formula I-1],

Ring A, Ring B, Ring C and Ring D represent a nitrogen-containing heterocycle in which any two rings of Rings A to D may have substituents, and the other two rings are aryl rings which may have substituents or A heteroaryl ring is represented and represented, and a condensed ring may be formed by ring A and ring B, ring A and ring C, and/or ring B and ring D. X ¹ , X ² , X ³ and X ⁴ represent a nitrogen atom in which two of them are coordinated to a platinum atom, and the other two represent a carbon atom or a nitrogen atom. Q ¹ , Q ² and Q ³ each independently represent a divalent atom (mono) or bond, but Q ¹ , Q ² and Q ³ do not simultaneously represent a bond. Z ¹ , Z ² , Z ³ and Z ⁴ , which 2 represents a coordination bond, and the other 2 represent a covalent bond, an oxygen atom or a sulfur atom.

Examples of the specific compound of [General Formula I-1] are as follows, but are not limited thereto.

[General Formula J-1]

In the above [General Formula J-1],

M represents the same metal ion as defined in [General Formula A-1], Ar1 represents a substituted or unsubstituted ring structure, and two azomethine bonds (-C=N-) that bind to the M In, the nitrogen atom (N) each binds to the M, and as a whole forms a tridentate ligand bonded to the M at three loci.

In addition, in Ar1, C represents a carbon atom constituting the ring structure represented by Ar1. In addition, R1 and R2 may be the same or different from each other, and each represents a substituted or unsubstituted alkyl or aryl group, and L represents a monodentate ligand.

In [General Formula J-1], it is preferable that M is Pt. Moreover, as said Ar1, it is preferable to select from 5-membered ring, 6-membered ring, and these condensed ring groups.

Examples of the specific compound of [General Formula J-1] are as follows, but are not limited thereto.

In addition, the emission layer may further include various hosts and various dopant materials in addition to the dopant and the host.

In addition, one or more layers selected from the hole injection layer, the hole transport layer, the electron blocking layer, the light emitting layer, the hole blocking layer, the electron transport layer and the electron injection layer may be formed by a single molecule deposition method or a solution process, wherein the deposition method Means a method of forming a thin film by evaporating a material used as a material for forming each layer through heating or the like in a vacuum or low pressure state, and the solution process is used as a material for forming each layer. It refers to a method of mixing a substance with a solvent and forming a thin film through a method such as inkjet printing, roll to roll coating, screen printing, spray coating, dip coating, spin coating, and the like.

In addition, 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 single color or white flat panel lighting device, and a single color or white flexible lighting device.

Hereinafter, the present invention will be described in more detail with reference to preferred embodiments. However, these examples are intended to illustrate the present invention in more detail, it will be apparent to those skilled in the art that the scope of the present invention is not limited thereby.

[ Synthetic example 1] Synthesis of Compound 1

[Scheme 1-1] Synthesis of [Intermediate 1-a]

[Intermediate 1-a]

1-Nitronaphthalene (97 g, 0.56 mol), methyl cyanoacetate (166.5 g, 1.68 mol), potassium cyanide (40.1 g, 0.62 mol), potassium hydroxide (62.9 g, 1.12 mol) were added and stirred. Next, 970 mL of dimethylformamide was added and stirred at 60°C overnight. After removing the solvent by concentrating under reduced pressure at room temperature, 500 mL of a 10% aqueous sodium hydroxide solution was added and refluxed for about 1 hour. After extraction with ethyl acetate, separation by column chromatography, and recrystallization with toluene and heptane gave [Intermediate 1-a] 50.8 g (yield 54%).

Scheme 1-2 Synthesis of [Intermediate 1-b]

[Intermediate 1-b]

[Intermediate 1-a] (25.0 g, 149 mmol) obtained in [Scheme 1-1] was added to 200 mL of tetrahydrofuran and stirred. Phenyl magnesium bromide (3.0 M in Et ₂ O) (87.4 mL, 297 mmol) was added dropwise and refluxed at 0° C. for about 1 hour. Ethyl chloroformate (19.4 g, 179 mmol) was added dropwise and refluxed for about 1 hour. The aqueous ammonium chloride solution was added until it became weakly acidic, and washed with water and heptane to obtain 32.4 g [Intermediate 1-b] (yield 80%).

[Scheme 1-3] Synthesis of [Intermediate 1-c]

[Intermediate 1-c]

[Intermediate 1-b] (30 g, 110 mmol) obtained in [Scheme 1-2] was added to about 80 mL of oxychloride and refluxed overnight. After cooling the temperature to -20 °C, distilled water was slowly added to about 400 mL. After washing with water, methanol and heptane, recrystallization with toluene and heptane gave [Intermediate 1-c] 14.1 g (yield 44%).

[Scheme 1-4] Synthesis of [Intermediate 1-d]

[Intermediate 1-d]

Carbazole (13.6 g, 81.3 mmol), 2,5-dibromonitrobenzene (45.6 g, 162.5 mmol), copper powder (10.3 g, 162.5 mmol), 18-crown-6 (4.3 g, 16.3 mmol), After adding 200 mL of 1,2-dichlorobenzene to potassium carbonate (33.7 g, 243.9 mmol), the mixture was refluxed at 180°C for 1 day. After high temperature filter, separation by column chromatography gave [Intermediate 1-d] 25.4 g (yield 85%).

[Scheme 1-5] Synthesis of [Intermediate 1-e]

[Intermediate 1-e]

[Intermediate 1-d] (16.5 g, 54.5 mmol) synthesized in [Scheme 1-4] was added to 200 mL of 1,2-dichlorobenzene, 250 mL of triethylphosphite was added and refluxed at 150° C. for 12 hours. Ordered. Cooled to room temperature and separated by column chromatography to obtain [Intermediate 1-e] 18.3 g (yield 53%).

[Scheme 1-6] Synthesis of [Intermediate 1-f]

[Intermediate 1-f]

[Intermediate 1-e] (10.7 g, 32 mmol), 3,5-diphenylphenylboronic acid (10.7 g, 39 mmol), tetrakis(triphenylphosphine) palladium synthesized in [Scheme 1-5] above (0.7 g, 0.64 mmol), potassium carbonate (8.9 g, 64 mmol) was added with 80 mL of 1,4-dioxane, 80 mL of toluene and 30 mL of distilled water and refluxed overnight. Extracted with ethyl acetate and recrystallized from dichloromethane and acetone to obtain [Intermediate 1-f] 11.6 g (yield 75%).

[Scheme 1-7] Synthesis of [Compound 1]

[Compound 1]

60% sodium hydride (1.0 g, 26 mmol) and 20 mL of dimethylformamide were added and stirred for about 30 minutes. [Intermediate 1-f] (10.7 g, 22 mmol) obtained in [Scheme 1-6] and 100 mL of dimethylformamide were added dropwise, followed by stirring for about 1 hour or more. [Intermediate 1-c] (7.6 g, 26.2 mmol) synthesized in [Scheme 1-3] and 100 mL of dimethylformamide were added and stirred overnight. The resulting solid was filtered by adding 600 mL of distilled water. Recrystallization with toluene gave [Compound 1] 9.7 g (60% yield).

MS (MALDI-TOF): m/z 738.28 [M ⁺ ]

[ Synthetic example 2] Synthesis of Compound 2

Scheme 2-1 Synthesis of [Intermediate 2-a]

[Intermediate 2-a]

9-nitrophenanthrene was used instead of 1-nitronaphthalene used in [Scheme 1-1], and pentadeutereo phenyl magnesium bromide was used instead of phenyl magnesium bromide used in [Scheme 1-2] [Scheme 1-1] To [Intermediate 2-a] (yield 56%) was obtained in the same manner as in [Scheme 1-3].

Scheme 2-2 Synthesis of [Intermediate 2-b]

[Intermediate 2-b]

The same method using 3-bromo-9H-carbazole instead of [Intermediate 1-e] used in [Scheme 1-6], and pentadeutereophenylboronic acid instead of 3,5-diphenylphenylboronic acid. [Intermediate 2-b] (yield 80%) was obtained.

Scheme 2-3 Synthesis of [Intermediate 2-c]

[Intermediate 2-b] synthesized in [Scheme 2-2] was used instead of the carbazole used in [Scheme 1-4], and in [Scheme 1-5] instead of 2,5-dibromonitrobenzene. Using the synthesized [Intermediate 1-e], [Intermediate 2-c] (yield 70%) was obtained.

Scheme 2-4 Synthesis of [Compound 2]

[Intermediate 2-c] synthesized in [Scheme 2-3] is used instead of [Intermediate 1-f] used in [Scheme 1-7], and [Scheme 2-1] is used instead of [Intermediate 1-c]. [Compound 2] (yield 53%) was obtained by the same method using [Intermediate 2-a] synthesized from.

MS (MALDI-TOF): m/z 806.32 [M ⁺ ]

[ Synthetic example 3] Synthesis of Compound 3

Scheme 3-1 Synthesis of [Intermediate 3-a]

[Intermediate 3-a]

[Intermediate 3-a] in the same manner as [Scheme 1-1] to [Scheme 1-3] using 2-nitronaphthalene instead of 1-nitronaphthalene used in [Scheme 1-1] (yield 44%) Got

Scheme 3-2 Synthesis of [Intermediate 3-b]

Instead of [Intermediate 1-e] used in [Scheme 1-6], [Intermediate 3-a] synthesized in [Scheme 3-1] is used, and instead of 3,5-diphenylphenylboronic acid, 1-bromo [Intermediate 3-b] (yield 79%) was obtained in the same manner using naphthalene-4-boronic acid.

Scheme 3-3 Synthesis of [Intermediate 3-c]

Using 2-bromo-1-nitrobenzene instead of 2,5-dibromonitrobenzene used in [Scheme 1-4], in the same manner as in [Scheme 1-4] to [Scheme 1-5] [ Intermediate 3-c] (yield 55%) was obtained.

Scheme 3-4 Synthesis of [Compound 3]

[Intermediate 3-c] synthesized in [Scheme 3-3] is used instead of [Intermediate 1-f] used in [Scheme 1-7], and [Scheme 3-2] is used instead of [Intermediate 1-c]. [Compound 3] (yield 55%) was obtained in the same manner using [Intermediate 3-b] synthesized from.

MS (MALDI-TOF): m/z 636.23 [M ⁺ ]

[ Synthetic example 4] Synthesis of Compound 4

Scheme 4-1 Synthesis of [Intermediate 4-a]

[Intermediate 4-a]

[Intermediate 1-a] (18.5 g, 0.11 mol) synthesized in [Scheme 1-1] was dissolved in 200 mL of dimethylformamide and stirred at 0°C. N-bromosuccinimide (20.1 g, 0.11 mol) was dissolved in 100 mL of dimethylformamide and slowly added dropwise over 1 hour. Stirred at room temperature for 12 hours. After filtering the excess distilled water, washed with methanol and recrystallized with toluene and methanol to obtain [Intermediate 4-a] 12.5 g (Yield 46%).

Scheme 4-2 Synthesis of [Intermediate 4-b]

[Intermediate 4-b]

Instead of [Intermediate 1-e] used in [Scheme 1-6], [Intermediate 4-a] synthesized in [Scheme 4-1] is used, and instead of 3,5-diphenylphenylboronic acid, phenylboronic acid is used. Using it, [Intermediate 4-b] (yield 78%) was obtained.

Scheme 4-3 Synthesis of [Intermediate 4-c]

[Intermediate 4-c]

Instead of [Intermediate 1-a] used in [Scheme 1-2], using [Intermediate 4-b] synthesized in [Scheme 4-2] above, [Scheme 1-2] to [Scheme 1-3] [Intermediate 4-c] (yield 45%) was obtained by the same method.

Scheme 4-4 Synthesis of [Intermediate 4-d]

Instead of [Intermediate 1-e] used in [Scheme 1-6], [Intermediate 4-c] synthesized in [Scheme 4-3] is used, and instead of 3,5-diphenylphenylboronic acid, 3,5- [Intermediate 4-d] (yield 78%) was obtained in the same manner using dibromobenzeneboronic acid.

Scheme 4-5 Synthesis of [Intermediate 4-e]

[Intermediate 4-d] synthesized in [Reaction Scheme 4-4] is used instead of [Intermediate 1-e] used in [Reaction Scheme 1-6], and phenylboronic acid is substituted for 3,5-diphenylphenylboronic acid. [Intermediate 4-e] (yield 55%) was obtained using the same method.

Scheme 4-6 Synthesis of [Intermediate 4-f]

[Intermediate 4-f] (yield 62%) was obtained in the same manner using 2-naphthaleneboronic acid instead of 3,5-diphenylphenylboronic acid used in [Scheme 1-6].

Scheme 4-7 Synthesis of [Compound 4]

[Intermediate 4-f] synthesized in [Scheme 4-6] is used instead of [Intermediate 1-f] used in [Scheme 1-7], and [Scheme 4-5] is used instead of [Intermediate 1-c]. [Compound 4] (yield 50%) was obtained in the same manner using [Intermediate 4-e] synthesized from.

MS (MALDI-TOF) 864.33 m/z [M ⁺ ]

[ Synthetic example 5] Synthesis of Compound 5

[Scheme 5-1] Synthesis of [Intermediate 5-a]

[Intermediate 5-a]

9-nitrophenanthrene was used instead of 1-nitronaphthalene used in [Scheme 1-1], and 4-biphenyl magnesium bromide was used instead of phenyl magnesium bromide used in [Scheme 1-2]. [Intermediate 5-a] (yield 43%) was obtained in the same manner as 1] to [Scheme 1-3].

Scheme 5-2 Synthesis of [Intermediate 5-b]

[Intermediate 5-b]

4-Bromo-9,9-dimethyl-9-fluorene (7.2 g, 26.5 mmol) was dissolved in 500 mL of tetrahydrofuran, the temperature was lowered to -78°C, and then 1.6 M normal-butyllithium (18.2 mL, 29.1 mmol) was slowly added dropwise and stirred for about 1 hour. Trimethyl borate (4.1 g, 39.7 mmol) was slowly added dropwise, followed by stirring at room temperature for about 3 hours. 14 mL of 1 M aqueous hydrochloric acid solution was added dropwise and stirred for 30 minutes. Extracted with ethyl acetate and recrystallized from dichloromethane and hexane to obtain [Intermediate 5-b] 4.6 g (yield 73%).

Scheme 5-3 Synthesis of [Intermediate 5-c]

[Intermediate 5-c] in the same manner using [Intermediate 5-b] synthesized in [Reaction Scheme 5-2] instead of 3,5-diphenylphenylboronic acid used in [Reaction Scheme 1-6] (Yield 66 %).

Scheme 5-4 Synthesis of Scheme 5

[Intermediate 5-c] synthesized in [Scheme 5-3] is used instead of [Intermediate 1-f] used in [Scheme 1-7], and [Scheme 5-1] is used instead of [Intermediate 1-c]. [Compound 5] (yield 62%) was obtained in the same manner using [Intermediate 5-a] synthesized from.

MS (MALDI-TOF) 828.33 m/z [M ⁺ ]

[ Synthetic example 6] Synthesis of Compound 6

[Scheme 6-1] Synthesis of [Intermediate 6-a]

[Intermediate 6-a]

[Intermediate 1-e] used in [Scheme 1-6], 3-chloro-6-nitroisoquinoline was used instead, and 3,5-diphenylphenylboronic acid was used instead of phenylboronic acid to [Intermediate. 6-a] (Yield 82%).

Scheme 6-2 Synthesis of [Intermediate 6-b]

[Intermediate 6-b]

The same method as in [Scheme 1-1] to [Scheme 1-3] using [Intermediate 6-a] synthesized in [Scheme 6-1] instead of 1-nitronaphthalene used in [Scheme 1-1] above [Intermediate 6-b] (Yield 44%) was obtained.

[Scheme 6-3] Synthesis of [Intermediate 6-c]

[Intermediate 6-c]

Methyl-2-aminobenzoate (87 g, 0.58 mol), 1-bromo-4-iodobenzene (135.1 g, 0.48 mol), palladium acetate (1.3 g, 0.006 mol), xanthos (10 g, 0.02) mol), cesium carbonate (217.5 g, 0.67 mol) was added with 2500 mL of toluene and refluxed for about 6 hours. After extraction with ethyl acetate, separation by column chromatography gave [Intermediate 6-c] 110 g (yield 75%).

Scheme 6-4 Synthesis of [Intermediate 6-d]

[Intermediate 6-d]

[Intermediate 6-c] (110 g, 0.36 mol) obtained in [Scheme 6-3] was added to 1650 mL of diisopropyl ether and stirred. 419 mL of methyl magnesium bromide was slowly added dropwise and stirred at 50° C. for 12 hours. After extraction with ethyl acetate, recrystallization with dichloromethane and hexane gave [Intermediate 6-d] 108 g (yield 68%).

[Scheme 6-5] Synthesis of [Intermediate 6-e]

[Intermediate 6-e]

[Intermediate 6-d] (108 g, 0.36 mol) obtained in [Scheme 6-4] and 400 mL of phosphoric acid were added and stirred for 6 hours. After the reaction was completed, excess distilled water was added, stirred, and filtered to separate by column chromatography to obtain [Intermediate 6-e] 75 g (yield 75%).

Scheme 6-6 Synthesis of [Intermediate 6-f]

[Intermediate 6-f]

Instead of [Intermediate 1-f] used in [Scheme 1-7], [Intermediate 6-e] synthesized in [Scheme 6-5] was used, and iodobenzene was used instead of [Intermediate 1-c]. [Intermediate 6-f] (yield 84%) was obtained by the method.

Scheme 6-7 Synthesis of [Intermediate 6-g]

[Intermediate 6-f] in the same manner using [Intermediate 6-f] synthesized in [Scheme 6-6] instead of 4-bromo-9,9-dimethyl-9-fluorene used in [Reaction Scheme 5-2]. -g] (yield 70%).

Scheme 6-8 Synthesis of [Intermediate 6-h]

Instead of [Intermediate 1-e] used in [Scheme 1-6], [Intermediate 1-e] synthesized in [Scheme 1-5] is used, and instead of 3,5-diphenylphenylboronic acid [Scheme 6-7] [Intermediate 6-h] obtained using [Intermediate 6-g] synthesized in [Intermediate 6-h] (yield 66%) was obtained.

Scheme 6-9 Synthesis of [Compound 6]

Instead of [Intermediate 1-f] used in [Scheme 1-7], [Intermediate 6-h] synthesized in [Scheme 6-8] is used, and instead of [Intermediate 1-c], [Scheme 6-2] [Compound 6] (yield 55%) was obtained in the same manner using [Intermediate 6-b] synthesized from.

MS (MALDI-TOF) 870.35 m/z [M ⁺ ]

[ Synthetic example 7] Synthesis of Compound 7

Scheme 7-1 Synthesis of [Intermediate 7-a]

[Intermediate 7-a]

[Intermediate 7-a] in the same manner as [Scheme 1-2] to [Scheme 1-3] using pyridin-4-yl magnesium bromide instead of the phenyl magnesium bromide used in [Scheme 1-2] (Yield 46 %).

Scheme 7-2 Synthesis of [Intermediate 7-b]

[Intermediate 7-a] synthesized in [Scheme 7-1] was used instead of [Intermediate 1-e] used in [Scheme 1-6], and 4-iodo instead of 3,5-diphenylphenylboronic acid. [Intermediate 7-b] (yield 75%) was obtained in the same manner using phenylboronic acid.

[Scheme 7-3] Synthesis of [Intermediate 7-c]

Same as using 4-bromo-1-naphthalenylboronic acid instead of [Intermediate 1-e] used in [Scheme 1-6] and 3-pyridylboronic acid instead of 3,5-diphenylphenylboronic acid. [Intermediate 7-c] (yield 78%) was obtained by the method.

[Scheme 7-4] Synthesis of [Intermediate 7-d]

[Intermediate 7-d] in the same manner using [Intermediate 7-c] synthesized in [Scheme 7-3] instead of 3,5-diphenylphenylboronic acid used in [Scheme 1-6] (Yield 62 %).

Scheme 7-5 Synthesis of [Compound 7]

Instead of [Intermediate 1-f] used in [Scheme 1-7], [Intermediate 7-d] synthesized in [Scheme 7-4] is used, and instead of [Intermediate 1-c], [Scheme 7-2] [Compound 7] (yield 60%) was obtained in the same manner using [Intermediate 7-b] synthesized from.

MS (MALDI-TOF) 790.28 m/z [M ⁺ ]

[ Synthetic example 8] Synthesis of Compound 8

[Scheme 8-1] Synthesis of [Intermediate 8-a]

[Intermediate 8-a]

9-nitrophenanthrene was used instead of 1-nitronaphthalene used in [Scheme 1-1], and 1-naphthyl magnesium bromide was used instead of phenyl magnesium bromide used in [Scheme 1-2]. [Intermediate 8-a] (yield 44%) was obtained by the same method as 1] to [Scheme 1-3].

Scheme 8-2 Synthesis of [Intermediate 8-b]

[Intermediate 8-b] (yield 86%) was obtained in the same manner using 3-azacarbazole instead of [Intermediate 1-a] used in [Scheme 4-1].

[Scheme 8-3] Synthesis of [Intermediate 8-c]

Instead of [Intermediate 1-f] used in [Scheme 1-7], [Intermediate 8-b] synthesized in [Scheme 8-2] is used, and iodobenzene is used instead of [Intermediate 1-c]. [Intermediate 8-c] (yield 82%) was obtained by the method.

Scheme 8-4 Synthesis of [Intermediate 8-d]

[Intermediate 8] in the same manner using [Intermediate 8-c] synthesized in [Reaction 8-3] above instead of 4-bromo-9,9-dimethyl-9-fluorene used in [Reaction Scheme 5-2]. -d] (Yield 77%).

[Scheme 8-5] Synthesis of [Intermediate 8-e]

[Intermediate 8-e] in the same manner using [Intermediate 8-d] synthesized in [Reaction Scheme 8-4] instead of 3,5-diphenylphenylboronic acid used in [Reaction Scheme 1-6] (Yield 62 %).

Scheme 8-6 Synthesis of [Compound 8]

Instead of [Intermediate 1-f] used in [Scheme 1-7], [Intermediate 8-e] synthesized in [Scheme 8-5] is used, and instead of [Intermediate 1-c], [Scheme 8-1] [Compound 8] (yield 58%) was obtained by the same method using [Intermediate 8-a] synthesized from.

MS (MALDI-TOF) 852.30 m/z [M ⁺ ]

[ Synthetic example 9] Synthesis of Compound 9

Scheme 9-1 Synthesis of [Intermediate 9-a]

[Intermediate 9-a]

6-Nitro-1-naphthalenol (26.5 g, 0.14 mol) was added to 270 mL of dichloromethane and stirred. Pyridine (14 g, 0.18 mol) was added, cooled to 0° C., and trifluoromethane sulfonic anhydride (42.3 g, 0.15 mol) was slowly added dropwise, followed by stirring at room temperature for about 1 hour. Separation by column chromatography gave [Intermediate 9-a] 34.2 g (yield 76%).

Scheme 9-2 Synthesis of [Intermediate 9-b]

[Intermediate 9-b]

[Intermediate 9-a] synthesized in [Reaction Scheme 9-1] was used instead of [Intermediate 1-e] used in [Scheme 1-6], and phenyl boronic acid was substituted for 3,5-diphenylphenylboronic acid. Using the same method, [Intermediate 9-b] (yield 90%) was obtained.

[Scheme 9-3] Synthesis of [Intermediate 9-c]

[Intermediate 9-c]

Using [Intermediate 9-b] synthesized in [Scheme 9-2] instead of 1-nitronaphthalene used in [Scheme 1-1], in the same manner as in [Scheme 1-1] to [Scheme 1-3] [Intermediate 9-c] (Yield 43%) was obtained.

Scheme 9-4 Synthesis of [Intermediate 9-d]

[Intermediate 9-d] (yield 68%) was obtained by using 4-(1-naphthyl)phenylboronic acid instead of 3,5-diphenylphenylboronic acid used in [Scheme 1-6].

Scheme 9-5 Synthesis of [Compound 9]

[Intermediate 9-d] synthesized in [Scheme 9-4] is used instead of [Intermediate 1-f] used in [Scheme 1-7], and [Scheme 9-3] is used instead of [Intermediate 1-c]. [Compound 9] (yield 63%) was obtained in the same manner using [Intermediate 9-c] synthesized from.

MS (MALDI-TOF) 788.29 m/z [M ⁺ ]

[ Synthetic example 10] Synthesis of Compound 10

Scheme 10-1 Synthesis of [Intermediate 10-a]

[Intermediate 10-a]

Hepta deutereo nitronaphthalene was used instead of 1-nitronaphthalene used in [Scheme 1-1], and pentadeutereo phenyl magnesium bromide was used instead of phenyl magnesium bromide used in [Scheme 1-2]. [Intermediate 10-a] (yield 45%) was obtained in the same manner as 1] to [Scheme 1-3].

Scheme 10-2 Synthesis of [Intermediate 10-b]

[Intermediate 10-b] (yield 75%) was obtained in the same manner as in [Scheme 1-6] using pentadeutereo phenylboronic acid instead of 3,5-diphenylphenylboronic acid.

Scheme 10-3 Synthesis of [Compound 10]

Instead of [Intermediate 1-f] used in [Scheme 1-7], [Intermediate 10-b] synthesized in [Scheme 10-2] is used, and instead of [Intermediate 1-c], [Scheme 10-1] [Compound 10] (yield 65%) was obtained in the same manner using [Intermediate 10-a] synthesized from.

MS (MALDI-TOF) 602.32 m/z [M ⁺ ]

[ Synthetic example 11] Synthesis of Compound 11

[Scheme 11-1] Synthesis of [Intermediate 11-a]

Instead of [Intermediate 1-e] used in [Scheme 1-6], [Intermediate 3-a] synthesized in [Scheme 3-1] is used, and instead of 3,5-diphenylphenylboronic acid, 6-chloro- [Intermediate 11-a] (yield 70%) was obtained in the same manner using 2-naphthylboronic acid.

Scheme 11-2] Synthesis of [Intermediate 11-b]

In the same manner as in [Scheme 1-4] to [Scheme 1-5], using 2,4-dibromonobenzene instead of 2,5-dibromonitrobenzene used in [Scheme 1-4] above [ Intermediate 11-b] (Yield 54%) was obtained.

[Scheme 11-3] Synthesis of [Intermediate 11-c]

In [Scheme 1-6], instead of 3,5-diphenylphenylboronic acid, 4-phenylpyridine-2-boronic acid was used to obtain [Intermediate 11-c] (yield 70%).

Scheme 11-4 Synthesis of [Compound 11]

Instead of [Intermediate 1-f] used in [Scheme 1-7], [Intermediate 11-c] synthesized in [Scheme 11-3] is used, and instead of [Intermediate 1-c], [Scheme 11-1] [Compound 11] (yield 60%) was obtained by the same method using [Intermediate 11-a] synthesized from.

MS (MALDI-TOF) 789.29 m/z [M ⁺ ]

[ Synthetic example 12] Synthesis of Compound 12

Scheme 12-1 Synthesis of [Intermediate 12-a]

Instead of [Intermediate 1-e] used in [Scheme 1-6], [Intermediate 1-c] synthesized in [Scheme 1-3] is used, and 4-bromobi instead of 3,5-diphenylphenylboronic acid. [Intermediate 12-a] (yield 77%) was obtained by the same method using phenyl-4'-boronic acid.

Scheme 12-2 Synthesis of [Intermediate 12-b]

Same as using 4-chloro-2-fluorophenylboronic acid instead of [Intermediate 1-e] used in [Scheme 1-6] and 2-naphthaleneboronic acid instead of 3,5-diphenylphenylboronic acid. [Intermediate 12-b] (yield 70%) was obtained by the method.

Scheme 12-3 Synthesis of [Intermediate 12-c]

Instead of [Intermediate 1-e] used in [Scheme 1-6], [Intermediate 11-b] synthesized in [Scheme 11-2] is used, and instead of 3,5-diphenylphenylboronic acid, [Scheme 12] [Intermediate 12-c] (yield 65%) was obtained in the same manner using [Intermediate 12-b] synthesized in -2].

Scheme 12-4 Synthesis of [Compound 12]

[Intermediate 12-c] synthesized in [Scheme 12-3] is used instead of [Intermediate 1-f] used in [Scheme 1-7], and [Scheme 12-1] is used instead of [Intermediate 1-c]. [Compound 12] (yield 61%) was obtained in the same manner using [Intermediate 12-a] synthesized from.

MS (MALDI-TOF) 882.32 m/z [M ⁺ ]

[ Synthetic example 13] Synthesis of Compound 13

Scheme 13-1 Synthesis of [Intermediate 13-a]

[Intermediate 13-a]

1,4-dibromobenzene (15 g, 63.58 mmol) was added to 300 mL of tetrahydrofuran, and 1.6 M normal-butyllithium (26.7 mL, 66.76 mmol) was slowly added dropwise at -78°C, followed by stirring for 1 hour. 20.6 mL of chlorotriphenylsilane was dissolved in 70 mL of tetrahydrofuran and added, followed by stirring at room temperature for 12 hours. Extracted with ethyl acetate and recrystallized with ethyl acetate and methanol to obtain [Intermediate 13-a] 17.5 g (yield 66%).

Scheme 13-2 Synthesis of [Intermediate 13-b]

[Intermediate 13-b]

[Intermediate 13-A] was prepared in the same manner using [Intermediate 13-a] synthesized in [Reaction 13-1] instead of 4-bromo-9,9-dimethyl-9-fluorene used in [Reaction Scheme 5-2]. -b] (yield 70%).

Scheme 13-3 Synthesis of [Intermediate 13-c]

Instead of [Intermediate 1-e] used in [Scheme 1-6], [Intermediate 11-b] synthesized in [Scheme 11-2] is used, and instead of 3,5-diphenylphenylboronic acid, [Scheme 13] [Intermediate 13-c] (yield 70%) was obtained in the same manner using [Intermediate 13-b] synthesized in -2].

Scheme 13-4 Synthesis of [Compound 13]

[Intermediate 13-c] synthesized in [Scheme 13-3] is used instead of [Intermediate 1-f] used in [Scheme 1-7], and [Scheme 2-1] is used instead of [Intermediate 1-c]. [Compound 13] (yield 62%) was obtained by the same method using [Intermediate 2-a] synthesized from.

MS (MALDI-TOF) 899.35 m/z [M ⁺ ]

[ Synthetic example 14] Synthesis of Compound 14

Scheme 14-1 Synthesis of [Intermediate 14-a]

[Intermediate 14-a]

Indole (50 g, 0.43 mol), 1-bromo-3-iodobenzene (181.1 g, 0.64 mol), copper powder (63.5 g, 0.85 mol), 18-crown-6 (22.6 g, 0.83 mol), Potassium carbonate (176.9 g, 1.29 mol) was added to 500 mL of 1,2-dichlorobenzene and refluxed at 180°C for one day. After high-temperature filter, separation by column chromatography gave [Intermediate 14-a] 48 g (Yield 41%).

Scheme 14-2 Synthesis of [Intermediate 14-b]

[Intermediate 14-b]

[Intermediate 14-A] was synthesized in the same manner using [Intermediate 14-a] synthesized in [Reaction 14-1] instead of 4-bromo-9,9-dimethyl-9-fluorene used in [Reaction Scheme 5-2]. -b] (Yield 76%).

Scheme 14-3 Synthesis of [Intermediate 14-c]

Instead of [Intermediate 1-e] used in [Scheme 1-6], [Intermediate 11-b] synthesized in [Scheme 11-2] is used, and instead of 3,5-diphenylphenylboronic acid, [Scheme 14] [Intermediate 14-c] (yield 67%) was obtained in the same manner using [Intermediate 14-b] synthesized in -2].

Scheme 14-4 Synthesis of [Compound 14]

Instead of [Intermediate 1-f] used in [Scheme 1-7], [Intermediate 14-c] synthesized in [Scheme 14-3] is used, and instead of [Intermediate 1-c], [Scheme 7-1] [Compound 14] (yield 63%) was obtained by the same method using [Intermediate 7-a] synthesized from.

MS (MALDI-TOF) 702.25 m/z [M ⁺ ]

[ Synthetic example 15] Synthesis of Compound 15

Scheme 15-1 Synthesis of [Intermediate 15-a]

Instead of [Intermediate 1-e] used in [Scheme 1-6], [Intermediate 1-c] synthesized in [Scheme 1-3] is used, and 5-chloropyridine instead of 3,5-diphenylphenylboronic acid. [Intermediate 15-a] (yield 72%) was obtained in the same manner using -2-boronic acid.

Scheme 15-2 Synthesis of [Intermediate 15-b]

3-Bromo-9H-carbazole is used instead of [Intermediate 1-e] used in [Scheme 1-6], and phenylboronic acid is used instead of 3,5-diphenylphenylboronic acid. 15-b] (Yield 82%).

Scheme 15-3 Synthesis of [Intermediate 15-c]

[Intermediate 15-c] (Yield 89%) in the same manner using [Intermediate 15-b] synthesized in [Reaction Scheme 15-2] instead of [Intermediate 1-a] used in [Reaction Scheme 4-1]. Got.

Scheme 15-4 Synthesis of [Intermediate 15-d]

Instead of [Intermediate 1-e] used in [Scheme 1-6], [Intermediate 15-c] synthesized in [Scheme 15-3] is used, and instead of 3,5-diphenylphenylboronic acid, 1-naphthaleneboron [Intermediate 15-d] (yield 75%) was obtained by the same method using an acid.

[Scheme 15-5] Synthesis of [Intermediate 15-e]

Instead of [Intermediate 1-f] used in [Scheme 1-7], [Intermediate 15-d] synthesized in [Scheme 15-4] is used, and instead of [Intermediate 1-c], [Scheme 11-2] [Intermediate 15-e] (yield 66%) was obtained in the same manner using [Intermediate 11-b] synthesized from.

Scheme 15-6 Synthesis of [Compound 15]

[Intermediate 15-e] synthesized in [Scheme 15-5] is used instead of [Intermediate 1-f] used in [Scheme 1-7], and [Scheme 15-1] is used instead of [Intermediate 1-c]. [Compound 15] (yield 50%) was obtained in the same manner using [Intermediate 15-a] synthesized from.

MS (MALDI-TOF) 954.35 m/z [M ⁺ ]

Hereinafter, structures of the organic light emitting compounds represented by [Compound 1] to [Compound 15] synthesized according to Synthesis Examples 1 to 15 of the present invention are illustrated.

[Compound 1] [Formula 2] [Formula 3]

[Compound 4] [Formula 5] [Formula 6]

[Compound 7] [Formula 8] [Formula 9]

[Compound 10] [Formula 11] [Formula 12]

[Compound 13] [Formula 14] [Formula 15]

[ Example 1 to 5] Preparation of organic light emitting diode

The ITO glass was patterned to have a light emitting area of 2 mm×2 mm and then washed. After mounting the substrate in the vacuum chamber, the base pressure was 1 × 10 ^-6 torr, and then the organic material was placed on the ITO DNTPD (700 Pa), α-NPB (300 Pa), compounds 1 to 5 + ( piq) ₂ Ir(acac) (10%) (300 )), Alq ₃ (350 Å), LiF (5 Å), Al (1,000 Å) The film was deposited in this order and measured at 0.4 mA.

The DNTPD, α-NPB, (piq) ₂ Ir(acac), and Alq ₃ structures are as follows.

[DNTPD] [α-NPB]

[(piq) ₂ Ir(acac)] [Alq ₃ ]

[ Comparative example One]

The organic light emitting diode device for Comparative Example 1 was manufactured in the same manner as in Example 1 using CBP which is generally used as a phosphorescent host material instead of the compounds prepared by the invention in the device structures of Examples 1 to 5 above. The structure is as follows.

[CBP]

For the organic electroluminescent devices manufactured according to Examples 1 to 5 and Comparative Example 1, voltage, luminance, color coordinates, and life were measured, and the results are shown in Table 1 below.

division Host Dopant Voltage (V) Luminance (Cd/㎡) CIEx CIEy Example 1 Compound 1 (piq) ₂ Ir(acac) 3.9 870 0.670 0.329 Example 2 Compound 2 (piq) ₂ Ir(acac) 4.0 895 0.671 0.329 Example 3 Compound 3 (piq) ₂ Ir(acac) 3.9 888 0.671 0.328 Example 4 Compound 4 (piq) ₂ Ir(acac) 4.1 906 0.672 0.329 Example 5 Compound 5 (piq) ₂ Ir(acac) 4.0 822 0.672 0.328 Comparative Example 1 CBP (piq) ₂ Ir(acac) 7.9 350 0.667 0.324

[ Example 6 to 11] Preparation of organic light emitting diode

The organic light emitting diode device for Examples 6 to 11 uses [Compound 7], [Compound 9], [Compound 10] to [Compound 12], and [Compound 15] in the light emitting layer in the device structures of Examples 1 to 5 above. It was produced in the same way using [Ir(ppy) ₃ ] instead of [(piq) ₂ Ir(acac)], and the structure of [Ir(ppy) ₃ ] is as follows.

[Ir(ppy) ₃ ]

[Comparative Example 2]

The organic light emitting diode device for Comparative Example 2 was manufactured in the same manner as in Comparative Example 1 by using [Ir(ppy) ₃ ] instead of [(piq) ₂ Ir(acac)] for the light emitting layer in the device structure of Comparative Example 1.

For the organic electroluminescent devices manufactured according to Examples 6 to 11 and Comparative Example 2, voltage, luminance, color coordinates and life were measured and the results are shown in Table 2 below.

division Host Dopant Voltage (V) Luminance (Cd/㎡) CIEx CIEy Example 6 Compound 7 Ir(ppy) ₃ 3.9 905 0.327 0.626 Example 7 Compound 9 Ir(ppy) ₃ 4.0 923 0.329 0.625 Example 8 Compound 10 Ir(ppy) ₃ 3.9 917 0.330 0.627 Example 9 Compound 11 Ir(ppy) ₃ 4.1 920 0.331 0.623 Example 10 Compound 12 Ir(ppy) ₃ 4.0 931 0.327 0.625 Example 11 Compound 15 Ir(ppy) ₃ 3.9 909 0.328 0.622 Comparative Example 2 CBP Ir(ppy) ₃ 7.5 401 0.29 0.622

As shown in [Table 1] and [Table 2], the organic compound secured by the present invention has a much lower driving voltage and luminance than CBP among host materials that are frequently used as phosphorescent host materials.

Claims (9)

The organic light emitting compound represented by any one selected from the following [Formula I] to [Formula III]:
[Formula Ⅰ] [Formula Ⅱ] [Formula Ⅲ]

In the above [Formula I] to [Formula III],
L is a single bond, a substituted or unsubstituted arylene group having 6 to 50 carbon atoms and a substituted or unsubstituted heteroarylene group having 2 to 50 carbon atoms, n is an integer from 0 to 3, and n is When 2 or more, a plurality of L are the same or different from each other,
R ₁ to R ₁₁ are the same or different from each other, and each independently hydrogen, deuterium, halogen group, cyano group, substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted aryl group having 6 to 50 carbon atoms and substitution Or an unsubstituted heteroaryl group having 2 to 50 carbon atoms,
X ₁ to X ₈ may be the same as or different from each other, each independently N or CR ₁₃ ,
R ₁₃ is hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, and a substituted or unsubstituted heterocycle having 2 to 50 carbon atoms. Selected from aryl groups,
R ₁₂ is selected from a substituted or unsubstituted aryl group having 6 to 50 carbon atoms and a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms. delete delete According to claim 1,
The L and R ₁ to R ₁₃ are each independently deuterium, cyano group, halogen group, hydroxy group, nitro group, alkyl group having 1 to 20 carbon atoms, alkenyl group having 2 to 20 carbon atoms, alkynyl group having 2 to 20 carbon atoms, carbon number 1 To a halogenated alkyl group of 20 to 20, aryl group of 6 to 24 carbon atoms, heteroaryl group of 2 to 24 carbon atoms, alkoxy group of 1 to 20 carbon atoms, aryloxy group of 6 to 24 carbon atoms, alkylsilyl group of 1 to 20 carbon atoms, carbon number An organic light-emitting compound, characterized in that it is further substituted with one or more substituents selected from 6 to 24 arylsilyl groups, alkylamine groups having 1 to 20 carbon atoms and arylamine groups having 6 to 24 carbon atoms. A first electrode; A second electrode; And at least one organic layer interposed between the first electrode and the second electrode.
The organic layer is an organic electroluminescent device characterized in that it comprises at least one organic light emitting compound represented by any one selected from [Formula I] to [Formula III] according to claim 1. The method of claim 5,
The organic layer comprises a hole injection layer, a hole transport layer, a functional layer having a hole injection function and a hole transport function simultaneously, at least one layer selected from a light emitting layer, an electron transport layer, and an electron injection layer. The method of claim 5,
The organic electroluminescent device, characterized in that the organic layer interposed between the first electrode and the second electrode includes a light emitting layer. The method of claim 7,
The light emitting layer is composed of a host compound and a dopant compound, the organic light emitting compound represented by any one selected from the above [Formula I] to [Formula III] is used as a host,
The light emitting layer is an organic electroluminescent device comprising at least one dopant compound. The method of claim 5,
An organic electroluminescent device characterized in that it further emits white light by further comprising at least one organic light emitting layer emitting red, green, or blue light on the organic layer.

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