KR102523256B1 - An organoelectro luminescent compounds and organoelectro luminescent device using the same - Google Patents

Abstract

The present invention relates to an organic light emitting compound represented by the following [Chemical Formula 1] and an organic electroluminescent device including the organic light emitting device. In comparison, the luminous efficiency is excellent, the driving voltage is remarkably low, and it has an excellent long lifespan.
[Formula 1]

Description

Organic light emitting compound and organic electroluminescent device containing the same {An organoelectro luminescent compounds and organoelectro luminescent device using the same}

The present invention relates to a novel organic light emitting compound and an organic light emitting device employing the same, capable of being driven at low voltage, and having improved light emitting efficiency and long lifespan.

Organic light emitting devices can not only be formed on a transparent substrate, but also can be driven at a low voltage of 10 V or less compared to plasma display panels or inorganic electroluminescent (EL) displays, and consume relatively little power. It has the advantage of being excellent in color and can show three colors of green, blue, and red, so it has recently become a subject of much interest as a next-generation display device.

However, in order for such an organic electroluminescent device to exhibit the above characteristics, hole injection materials, hole transport materials, light emitting materials, electron transport materials, electron injection materials, etc., which are materials constituting the organic layer in the device, are supported by stable and efficient materials. However, the development of stable and efficient organic material layer materials for organic light emitting devices has not yet been sufficiently achieved.

Therefore, the development of new materials having low voltage driving, high efficiency and long lifespan has been continuously demanded.

Meanwhile, the most important factor determining luminous efficiency in an organic light emitting device is a light emitting material included in a light emitting layer. Although fluorescent materials are currently widely used as light emitting materials, the development of phosphorescent materials is one of the theoretically possible ways to further improve light emitting efficiency due to the light emitting mechanism, and accordingly, various phosphorescent materials have been developed. In particular, organic electroluminescent devices using CBP and BALq derivatives as hosts have been known as phosphorescent host materials.

However, an organic electroluminescent device using a phosphorescent light emitting material has significantly higher current efficiency than a device using a fluorescent light emitting material. Since the driving voltage is higher than that, there is no great advantage in terms of power efficiency, and the lifespan of the device is not at a satisfactory level, so the development of a more stable and high-performance host material in terms of driving voltage and life characteristics is required.

Accordingly, an object of the present invention is to provide a novel organic light emitting compound, which is a phosphorescent light emitting host material, which can be employed in a light emitting layer of an organic light emitting device to realize excellent light emitting properties, 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 [Formula 1].

[Formula 1]

Details of the structure of [Formula 1] and each substituent will be described later.

In addition, the present invention is composed of a first electrode, a second electrode opposite to the first electrode, and one or more organic layers interposed between the first electrode and the second electrode, the organic layer represented by the above [Formula 1] It provides an organic electroluminescent device characterized in that it comprises at least one organic light emitting compound implemented.

The organic electroluminescent device employing the organic light emitting compound according to the present invention can be driven at a lower voltage and has improved luminous efficiency and longer lifespan compared to devices employing a conventional phosphorescent host compound in the light emitting layer.

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

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

One aspect of the present invention relates to a novel phosphorescent host compound that enables low-voltage driving by improving driving voltage characteristics, which have been pointed out as problems of conventional phosphorescent host compounds, and enables implementation of improved luminous efficiency and long lifespan characteristics, as follows [ It is characterized by being represented by Formula 1].

[Formula 1]

In the above [Formula 1],

A1 And A2 are the same as or different from each other, and each independently selected from a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 carbon atoms and a substituted or unsubstituted heteroaromatic hydrocarbon ring having 3 to 50 carbon atoms, preferably substituted or unsubstituted. It is selected from a cyclic aromatic hydrocarbon ring having 6 to 18 carbon atoms and a substituted or unsubstituted heteroaromatic hydrocarbon ring having 5 to 18 carbon atoms.

In addition, X ₁ to X ₃ are the same as or different from each other, and are each independently selected from the group consisting of S, O, NR ₁ , SiR ₂ R ₃ , GeR ₄ R ₅ , Se, and Te, wherein X ₁ to X ₃ At least one or more of them is characterized in that NR ₁ .

In addition, among the Y and Z, two adjacent Ys of the plurality of Ys are combined with '*' of the Q1 to form a condensed ring, and two adjacent Zs of the plurality of Zs are combined with '*' of the Q2 Forming a condensed ring, each of Y and Z bonded to '*' of Q1 or Q2 is a carbon atom, and each Y and Z that is not bonded is CR or N.

In addition, R and R ₁ to R ₅ are the same as or different from each other, and are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, or a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms. Or an unsubstituted C2-C30 alkynyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C2-C30 heterocycloalkyl group, or a substituted or unsubstituted C5-C30 cycloalkyl group. Alkenyl group, substituted or unsubstituted alkoxy group 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 carbon atoms An arylthio group having 5 to 30 carbon atoms, a substituted or unsubstituted alkylamine group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamine group having 5 to 30 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 carbon atoms, and a substituted Or an unsubstituted heteroaryl group having 3 to 50 carbon atoms, a substituted or unsubstituted silyl group, a substituted or unsubstituted germanium group, a substituted or unsubstituted boron group, a substituted or unsubstituted aluminum group, a carbonyl group, or a phosphoryl group. , a thiol group, a cyano group, a hydroxyl group, a nitro group, a halogen group, a selenium group, a tellurium group, an amide group, an ether group, and an ester group.

In addition, according to a preferred embodiment of the present invention, R ₁ in [Formula 1] is selected from a substituted or unsubstituted aryl group having 5 to 50 carbon atoms and a substituted or unsubstituted heteroaryl group having 3 to 50 carbon atoms do.

On the other hand, in the definition of [Formula 1] according to the present invention, 'substitution' in 'substituted or unsubstituted' refers to A1, A2, R, R ₁ to R ₅ and substituents thereof, etc. as one or more substituents. As meaning a further substituted case, the one or more substituents are specifically deuterium, cyano group, halogen group, hydroxy group, nitro group, C 1 to 24 alkyl group, C 1 to 24 halogenated alkyl group, C 1 to 24 of alkenyl group, C1-24 alkynyl group, C1-24 heteroalkyl group, C6-24 aryl group, C6-24 arylalkyl group, C2-24 heteroaryl group or C2-24 Heteroarylalkyl group, C1-24 alkoxy group, C1-24 alkylamino group, C1-24 arylamino group, C1-24 heteroarylamino group, C1-24 alkylsilyl group, C6-24 It is selected from the group consisting of an arylsilyl group and an aryloxy group having 6 to 24 carbon atoms.

In addition, the aryl group included in the organic light emitting compound according to the present invention is an organic radical derived from an aromatic hydrocarbon by removing one hydrogen, and is a single or fused ring system containing 5 to 7 members, preferably 5 or 6 members. In addition, when the aryl group has a substituent, it may be fused with neighboring substituents to further form a ring.

As specific examples of the aryl group, phenyl group, o-biphenyl group, m-biphenyl group, p-biphenyl group, o-terphenyl group, m-terphenyl group, p-terphenyl group, naphthyl group, anthryl group, phenanthryl group , aromatic groups such as pyrenyl, indenyl, fluorenyl, tetrahydronaphthyl, perylenyl, chrysenyl, naphthacenyl, fluoranthenyl and the like.

In addition, the aryl group may also be further substituted with one or more substituents selected from among the substituents described in the definition of R ₁ to R ₅ , and more specifically, at least one hydrogen atom in the aryl group is a deuterium atom, a halogen atom, a hydroxyl group, a nitro group, cyano group, silyl group, 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 "alkylamino group"), amidino group, hydrazine group, hydrazone group, carboxyl group, sulfonic acid group, phosphoric acid group, C1-24 alkyl group, C1-24 halogenated alkyl group, C1-24 alkenyl group, carbon number 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, a heteroarylalkyl group having 2 to 24 carbon atoms, etc. can be substituted.

The heteroaryl group included in the organic light emitting compound according to the present invention may be any one selected from [Structure Formula 1] to [Structural Formula 10].

[Formula 1] [Formula 2] [Formula 3] [Formula 4]

[Formula 5] [Formula 6] [Formula 7]

[Formula 8] [Formula 9] [Formula 10]

In [Structural Formula 1] to [Structural Formula 10],

T ₁ to T ₁₂ are the same as or different from each other, and are each independently C(R ₄₂ ), C(R ₄₃ )(R ₄₄ ), N, N(R ₄₅ ), O, S, Se, Te, Si( It may be any one selected from R ₄₆ )(R ₄₇ ) and Ge(R ₄₈ )(R ₄₉ ), T ₁ to T ₁₂ are not all carbon atoms at the same time, and the R ₄₂ to R ₄₉ are the same as each other. or different, each independently hydrogen, heavy hydrogen, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted aryl group having 5 to 30 carbon atoms, and a substituted or an unsubstituted heteroaryl group having 2 to 30 carbon atoms and having O, N, S or P as a heteroatom.

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

[Structural Formula 3-1]

In [Structural Formula 3-1], T ₁ to T ₇ are the same as defined in [Structural Formula 1] to [Structural Formula 10].

According to a preferred embodiment of the present invention, the [Structural Formula 1] to [Structural Formula 10] may be selected from the following [Structural Formula 11].

[Structural formula 11]

In [Structural Formula 11],

X is the same as the definition of R ₁ to R ₅ in [Formula 1], m is an integer of 1 to 11, and when m is 2 or more, a plurality of X's are the same as or different from each other, and in [Formula 1] It can be linked with defined substituents.

In addition, the organic light emitting compound of [Formula 1] according to the present invention may be more specifically selected from [Formula 2] to [Formula 165], but the specific compounds below are specific to [Formula 1] according to the present invention As an example, this does not limit the scope of the present invention [Formula 1].

As described above, the organic light emitting compound according to the present invention introduces various substituents into the core structure represented by [Chemical Formula 1], thereby implementing an organic light emitting compound having not only the inherent characteristics of the core structure but also the inherent characteristics of the introduced substituents. . For example, by introducing substituents used in the hole injection layer material, the hole transport layer material, the light emitting layer material, and the electron transport layer material of the organic light emitting device into the core structure, a material satisfying the requirements of each organic material layer can be implemented.

In particular, the organic light emitting compound according to the present invention has a structure represented by the above [Formula 1] and a characteristic substituent, so that it has more improved luminous efficiency and longer lifespan compared to the phosphorescent host compound employed in the conventional light emitting layer, and can be driven at low voltage. It enables the implementation of possible organic electroluminescent devices.

In addition, another aspect of the present invention relates to an organic electroluminescent device composed of a first electrode, a second electrode, and one or more organic layers interposed between the first electrode and the second electrode, wherein the [Formula 1] ] may include at least one organic light emitting compound according to the present invention.

That is, the organic light emitting device according to an embodiment of the present invention may have a structure including a first electrode and a second electrode and an organic material layer disposed therebetween, and the organic light emitting compound of [Formula 1] according to the present invention It can be manufactured using conventional device manufacturing methods and materials, except that is used for the organic layer of the device.

The organic material layer of the organic light emitting device according to the present invention may have a single-layer structure, or may have a multi-layer structure in which two or more organic material layers are stacked. For example, it may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like. However, it is not limited thereto and may include fewer or more organic material layers.

Therefore, in the organic electroluminescent device of the present invention, the organic material layer may include at least one of a hole injection layer, a hole transport layer, and a hole injection and hole transport layer simultaneously, and at least one of the layers may include the [Chemical Formula 1] may be included.

In addition, in the organic electroluminescent device of the present invention, the organic material layer may include at least one of an electron injection layer, an electron transport layer, and a layer that simultaneously injects and transports electrons, and at least one of the layers is the [Formula 1] may be included.

Preferably, the organic material layer may include a light emitting layer, and the light emitting layer may include the compound represented by Formula 1.

Here, the compound represented by [Formula 1] may be included as a host material in the light emitting layer. When the compound represented by Formula 1 is included as a host material in the light emitting layer, the light emitting layer may further include one or more dopant compounds. As such, in the present invention, a dopant material may be used in the light emitting layer along with a host. When the light emitting layer includes a host and a dopant, the content of the dopant may be typically selected in the range of about 0.01 to about 20 parts by weight based on about 100 parts by weight of the host.

In addition, the compound represented by [Formula 1] in the multi-layered organic layer may be included in a light emitting layer, a layer that simultaneously performs hole injection/transportation and light emission, a layer that simultaneously transports holes and light emission, or a layer that simultaneously transports electrons and emits light. can

Hereinafter, an embodiment of an organic light emitting device according to the present invention will be described in more detail with reference to FIG. 1 .

1 is a cross-sectional view showing the structure of an organic electroluminescent device according to the present invention. The organic electroluminescent 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 may further include a hole injection layer 30 and an electron injection layer 70 as needed, and in addition to that, it is possible to further form a first or second intermediate layer, a hole blocking layer Alternatively, an electron blocking layer may be further formed, and an organic layer having various functions according to characteristics of the device may be further included.

Referring to FIG. 1, the organic light emitting device of the present invention and its manufacturing method will be described as follows.

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

The hole injection layer 30 is formed by vacuum thermal deposition or spin coating of a hole injection layer material on the anode 20 electrode. Next, the hole transport layer 40 is formed by vacuum thermal evaporation or spin coating of a hole transport layer material on the hole injection layer 30 .

The hole injection layer material may be used without particular limitation, as long as it is commonly used in the art, in addition to the organic light emitting compound according to the present invention. As a specific 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] and the like can be used.

In addition, the hole transport layer material is not particularly limited as long as it is commonly used in the art other than the organic light emitting compound according to the present invention, 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) etc. can be used.

Then, the organic light emitting layer 50 is laminated on top of the hole transport layer 40, and a hole blocking layer (not shown) is selectively formed on top of the organic light emitting layer 50 by vacuum deposition or spin coating. can do. The hole-blocking layer serves to prevent this problem by using a material having a very low HOMO (Highest Occupied Molecular Orbital) level because the lifespan and efficiency of the device are reduced when holes pass through the organic light emitting layer and flow into the cathode. . At this time, the hole-blocking material used is not particularly limited, but should have electron transport ability and higher ionization potential than the light emitting compound, and typically BAlq, BCP, TPBI, and the like may be used.

As a material used for the hole blocking layer, any one selected from BAlq, BCP, Bphen, TPBI, NTAZ, BeBq ₂ , OXD-7, Liq, and [Formula 501] to [Formula 507] may be used, but is limited thereto it is not going to be

BAlq BCP Bphen

TPBI NTAZ BeBq ₂

OXD-7 Liq

[Formula 501] [Formula 502] [Formula 503]

[Formula 504] [Formula 505] [Formula 506]

[Formula 507]

After depositing the electron transport layer 60 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-heated on top of the electron injection layer 70. The organic EL device is completed by depositing and forming the cathode 80 electrode. Here, the metal for forming the cathode is lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver ( Mg-Ag) may be used, and a transmissive cathode using ITO or IZO may be used to obtain a top light emitting device.

The electron transport layer material has a function of stably transporting electrons injected from the electron injection electrode (cathode), and other than the organic light emitting compound according to the present invention, a known electron transport material may be used. Examples of known electron transport materials are quinoline derivatives, in particular tris(8-quinolinolate)aluminum (Alq3), TAZ, Balq, beryllium bis(benzoquinolin-10-noate) (beryllium bis(benzoquinolin-10- olate: Bebq2), ADN, [Formula 401], [Formula 402], oxadiazole derivatives such as PBD, BMD, and BND may also be used.

TAZ BAlq

[Compound 401] [Compound 402] BCP

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

[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 to form a coordinate bond to M It is a ligand chelated by a single bond and a coordinate 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 coordinate bond with M, wherein 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 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 group 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 and having O, N or S as a heteroatom.

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

'Substitution' in 'substituted or unsubstituted' refers to heavy hydrogen, a cyano group, a halogen group, a hydroxyl group, a nitro group, an alkyl group, an alkoxy group, an alkylamino group, an arylamino group, a heteroarylamino group, an alkylsilyl group, an arylsilyl group, It means that it is substituted with one or more substituents selected from the group consisting of an aryloxy group, an aryl group, a heteroaryl group, germanium, phosphorus, and boron.

In addition, each of Y is the same or different, and may be independently any one selected from the following [Structural Formula C1] to [Structural Formula C39], but is not limited thereto.

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

[Formula C4] [Formula C5] [Formula C6]

[Formula C7] [Formula C8] [Formula C9] [Formula C10]

[Formula C11] [Formula C12] [Formula C13]

[Formula C14] [Formula C15] [Formula C16]

[Formula C17] [Formula C18] [Formula C19] [Formula C20]

[Formula C21] [Formula C22] [Formula C23]

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

[structural formula C27] [structural formula C28] [structural formula C29] [structural formula C30]

[Formula C31] [Formula C32] [Formula C33]

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

[Formula C37] [Formula C38] [Formula C39]

In the above [structural formula C1] to [structural formula C39],

R are the same as or different from each other, and are each independently hydrogen, heavy hydrogen, halogen, a cyano group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a 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 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 linked with adjacent substituents through alkylene or alkenylene to form a spiro ring or a 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, or a substituted or unsubstituted alkyl group having 5 to 30 carbon atoms It is selected from a heteroaryl group and a substituted or unsubstituted cycloalkyl group having 5 to 30 carbon atoms, wherein 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, and a carbon atom having 3 to 20 carbon atoms. It is further substituted with one or more substituents selected from a heteroaryl group, a cyano group, a halogen group, deuterium, and hydrogen, and is connected to an adjacent substituent with an alkylene or alkenylene to form a spiro ring or a fused ring.

In addition, in the organic electroluminescent device according to the present invention, the organic layer includes a light emitting layer, the light emitting layer may further include one or more dopant compounds, and the light emitting dopant compound applied to the organic light emitting device of the present invention Although not particularly limited, it may be one or more compounds selected from compounds represented by the following [General Formula A-1] to [General Formula J-1].

[Formula A-1]

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 may be the same as or different from each other as ligands, and each independently may include any one selected from [Formula D] below, but is not limited thereto. In addition, * in the following [Structural Formula D] represents a site that binds to the metal ion M.

[Structural Formula D]

In the above [structural formula D],

Wherein R are different or identical to each other and are 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 An unsubstituted C1-C30 alkylamino group, a substituted or unsubstituted C1-C30 alkylsilyl group, a substituted or unsubstituted C6-C30 arylamino group, and a substituted or unsubstituted C6-C30 arylsilyl group. It may be any one selected from groups.

Wherein R is each independently selected from 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, a heteroaryl group having 3 to 20 carbon atoms, a cyano group, a halogen group, deuterium and hydrogen It may be further substituted with one or more substituents.

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

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

As an example, the dopant represented by [General Formula A-1] may be any one selected from the following compounds, but is not limited thereto.

[Formula B-1]

In the above [General Formula B-1],

M ^A1 represents the same metal ion as defined in [General Formula A-1], Y ^A11 , Y ^A14 , Y ^A15 and Y ^A18 each independently represent 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, or a sulfur atom, and L ^A11 , L ^A12 , L ^A13 , and L ^A14 are each a linking group as defined above. , and Q ^A11 and Q ^A12 represent partial structures containing atoms bonded to M ^A1 .

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

[Formula C-1]

In [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, or a sulfur atom, L ^B11 , L ^B12 , L ^B13 , L ^B14 represent a linking group, and Q ^B11 , Q ^B12 are Represents a partial structure containing an atom bonded to M ^B1 .

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

[Formula D-1]

In the above [General Formula D-1],

M ^C1 represents 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 to form a 5-membered ring, and no 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, and a substituent without any linking to each other, G ^C11 , G ^C12 each independently represents a nitrogen atom, substituted or an unsubstituted carbon atom, L ^C11 and L ^C12 represent a linking group, and Q ^C11 and Q ^C12 represent a partial structure containing an atom bonded to M ^C1 .

An 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 or a substituted or unsubstituted carbon atom, and J ^D11 , J ^D12 , J ^D13 and J ^D14 each independently represents a group of atoms required to form a 5-membered ring, and L ^D11 and L ^D12 represent a linking group.

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

[Formula F-1]

In the above [general formula F-1],

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

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

[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 linking groups, R ^F11 , R ^F12 , R ^F13 and R ^F14 represent substituents, R ^F11 and R ^F12 , R F12 and R ^F13 , R ^F13 and R ^F14 are connected to each other ^, A ring may be formed, and in this case, the ring formed by R ^F1 and R ^F12 , and between R ^F13 and R ^F14 is a 5-membered ring. Further, Q ^F11 and Q ^F12 represent a partial structure containing an atom bonded to M ^F1 .

An 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 [General Formula H-1] to [Formula H-3],

R ¹¹ and R ¹² are alkyl, aryl or heteroaryl substituents; In addition, a fused ring may be formed with substituents adjacent to each other, and q11 and q12 may be integers of 0 to 4, preferably 0 to 2.

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

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

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

In addition, it is preferable that n ¹ and m ¹ make the metal complex represented by the general formula H-1 a neutral complex.

In the [general formula H-2],

R ²¹ , R ²² , n ² , m ² , q ²² , and L ² are the same as R ¹¹ , R ¹² , n ¹ , m ¹ , q ¹² , and L ¹ respectively, and q ²¹ is an integer from 0 to 2; , 0 is preferred.

In the above [general formula H-3],

R ³¹ , n ³ , m ³ , and L ³ are the same as R ¹¹ , n ¹ , m ¹ , and L ¹ respectively, and q ³¹ represents an integer of 0 to 8, preferably 0 to 2, and more preferably 0. desirable.

Examples of specific compounds of [Formula H-1] to [Formula H-3] are as follows, but are not limited thereto.

[Formula I-1]

In the above [General Formula I-1],

Ring A, Ring B, Ring C, and Ring D represent nitrogen-containing heterocycles in which any two rings of the rings A to D may have substituents, and the remaining two rings are aryl rings or heterocycles in which any two rings may have substituents. It represents and represents an aryl ring, and can form a condensed ring with Ring A and Ring B, Ring A and Ring C, and/or Ring B and Ring D. Any two of X ¹ , X ² , X ³ and X ⁴ represent a nitrogen atom coordinating with a platinum atom, and the other two represent a carbon atom or a nitrogen atom. Q ¹ , Q ² and Q ³ each independently represents a divalent atom (group) or bond, but Q ¹ , Q ² and Q ³ do not represent a bond simultaneously. Any two of Z ¹ , Z ² , Z ³ and Z ⁴ represent a coordination bond, and the other two represent a covalent bond, an oxygen atom or a sulfur atom.

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

[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-) bonded to M In , nitrogen atoms (N) are each bonded to the M, and form a tridentate ligand bonded to the M as a whole at the third position.

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

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

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

In addition, the light emitting 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 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 forming a thin film by mixing a material to be formed with a solvent and using the same 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 may be used in a device selected from a flat panel display device, a flexible display device, a monochromatic or white flat panel lighting device, and a monochromatic or white flexible lighting device.

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

<Synthesis example>

<Synthesis Example 1> Synthesis of a compound represented by [Formula 102]

(1) Synthesis of the compound represented by [Formula 1-a]

The compound represented by [Formula 1-a] was synthesized according to the following [Reaction Scheme 1].

[Scheme 1]

After dissolving 70.0 g (266 mmol) of 2-bromodibenzothiophene in 560 mL of tetrahydrofuran under nitrogen in a dried 1L reactor, 200 mL (319 mmol) of 1.6 n-butyllithium was slowly added dropwise while stirring at -78 °C. do. Upon completion of the dropwise addition, the mixture was stirred for 1 hour while maintaining -78 °C. 41.5 g (399 mmol) of trimethyl borate was slowly added dropwise, and the temperature of the reaction mixture was raised to room temperature and stirred for 3 hours. When the reaction is complete, 200 mL of 2 M aqueous hydrochloric acid solution is added, stirred for 30 minutes, and extracted with ethyl acetate and water. The organic layer was treated with magnesium sulfate to remove moisture, concentrated under reduced pressure, and recrystallized from methylene chloride and heptane to obtain 48.0 g of a compound represented by [Formula 1-a]. (yield 80%)

(2) Synthesis of the compound represented by [Formula 1-b]

The compound represented by [Formula 1-b] was synthesized according to the following [Reaction Scheme 2].

[Scheme 2]

48.0 g (211 mmol) of the compound represented by [Formula 1-a] obtained from [Scheme 1], 54.0 g (192 mmol) of 1,4-dibromo-2-nitrobenzene, tetrakis (triphenylphosphine) ) 4.4 g (4 mmol) of palladium, 53.1 g (384 mmol) of potassium carbonate, 270 mL of 1,4-dioxane, 270 mL of toluene, and 100 mL of distilled water were added and stirred under reflux for 12 hours. When the reaction is complete, extraction is performed using ethyl acetate and distilled water. The organic layer was concentrated under reduced pressure and separated by column chromatography to obtain 61.2 g of a compound represented by [Formula 1-b]. (Yield 83%)

(3) Synthesis of the compound represented by [Formula 1-c]

The compound represented by [Formula 1-c] was synthesized according to the following [Reaction Scheme 3].

[Scheme 3]

61.2 g (159 mmol) of the compound represented by [Formula 1-b] obtained from [Scheme 2] and 167.1 g (637 mmol) of triphenylphosphine were put in 610 mL of dichlorobenzene and stirred under reflux for 12 hours. After completion of the reaction, after concentration, it was separated by column chromatography to obtain 31.9 g of the compound represented by [Formula 1-c]. (Yield 56.9%)

(4) Synthesis of the compound represented by [Formula 1-d]

The compound represented by [Formula 1-d] was synthesized according to the following [Scheme 4].

[Scheme 4]

31.9 g (91 mmol) of the compound represented by [Formula 1-c] obtained from [Scheme 3], 24 g (118 mmol) of iodobenzene, 20.7 g (181 mmol) of 1,2-cyclohexanidinamine, 0.9 g (5 mmol) of copper iodide, 40.4 g (190 mmol) of tribasic potassium phosphate, and 255 mL of 1,4-dioxane were added and stirred under reflux for 12 hours. When the reaction is complete, filter under reduced pressure in a hot state. The solution was concentrated under reduced pressure and separated by column chromatography to obtain 30.3 g of the compound represented by [Formula 1-d]. (Yield 78.2%)

(5) Synthesis of the compound represented by [Formula 1-e]

The compound represented by [Formula 1-e] was synthesized according to the following [Scheme 5].

[Scheme 5]

After dissolving 100.0 g (495 mmol) of 1-bromo-2-nitrobenzene in 800 mL of tetrahydrofuran under nitrogen in a dried 2L reactor, 370 mL (594 mmol) of 1.6 n-butyllithium was added while stirring at -78 ° C. is slowly added dropwise. Upon completion of the dropwise addition, the mixture was stirred for 1 hour while maintaining -78 °C. 77.2 g (743 mmol) of trimethyl borate was slowly added dropwise, and the temperature of the reaction mixture was raised to room temperature and stirred for 3 hours. When the reaction is complete, 400 mL of 2 M aqueous hydrochloric acid solution is added, stirred for 30 minutes, and extracted with ethyl acetate and water. The organic layer was treated with magnesium sulfate to remove moisture, concentrated under reduced pressure, and recrystallized from methylene chloride and heptane to obtain 60.2 g of a compound represented by [Formula 1-e]. (Yield 73.0%)

(6) Synthesis of the compound represented by [Formula 1-f]

The compound represented by [Formula 1-f] was synthesized according to the following [Scheme 6].

[Scheme 6]

30.3 g (71 mmol) of the compound represented by [Formula 1-d] obtained from [Reaction Formula 4], 14.2 g (85 mmol) of the compound represented by [Formula 1-e] obtained from [Reaction Formula 5], tetrakis 1.6 g (1 mmol) of (triphenylphosphine)palladium, 19.6 g (141 mmol) of potassium carbonate, 300 mL of 1,4-dioxane, 300 mL of toluene, and 120 mL of distilled water were added and stirred under reflux for 12 hours. When the reaction is complete, extraction is performed using ethyl acetate and distilled water. The organic layer was concentrated under reduced pressure and separated by column chromatography to obtain 25.7 g of a compound represented by [Formula 1-f]. (Yield 76.9%)

(7) Synthesis of the compound represented by [Formula 1-g]

The compound represented by [Formula 1-g] was synthesized according to the following [Scheme 7].

[Scheme 7]

25.7 g (55 mmol) of the compound represented by [Formula 1-f] obtained from [Scheme 6] and 57.3 g (218 mmol) of triphenylphosphine were put in 260 mL of dichlorobenzene and stirred under reflux for 12 hours. After completion of the reaction, after concentration, it was separated by column chromatography to obtain 6.6 g of the compound represented by [Formula 1-g]. (Yield 27.4%)

(8) Synthesis of the compound represented by [Formula 1-h]

The compound represented by [Formula 1-h] was synthesized according to the following [Scheme 8].

[Scheme 8]

After filling the dried 2L reactor with nitrogen, 45.0 g (381 mmol) of 2-aminobenzonitrile and 405 mL of tetrahydrofuran were added, and 279 mL (838 mmol) of 3 M-phenylmagnesium bromide was slowly added dropwise at 0 ° C. while stirring under reflux. When the starting material disappears, lower the temperature again, dissolve 62.0 g (0.571 mmol) of ethyl chloroformate in 200 mL of tetrahydrofuran, add slowly dropwise, and stir under reflux for 2 hours. When the reaction is complete, an aqueous solution of ammonium chloride is added and extracted with ethyl acetate and water. The organic layer was concentrated under reduced pressure and separated by column chromatography to obtain 50.0 g of a compound represented by [Formula 1-h]. (Yield 58.0%)

(9) Synthesis of the compound represented by [Formula 1-i]

The compound represented by [Formula 1-i] was synthesized according to the following [Scheme 9].

[Scheme 9]

50.0 g (225 mmol) of the compound represented by [Formula 1-h] obtained from [Scheme 8] was added to 500 mL of phosphorus oxychloride and stirred under reflux for 5 hours. When the reaction is complete, the temperature is lowered and the mixture is slowly added dropwise to water. After the dropwise addition is completed, the produced solid is filtered and then extracted with methylene chloride and water. The organic layer was concentrated under reduced pressure and separated by column chromatography to obtain 41 g of a compound represented by [Formula 1-i]. (Yield 75.1%)

(10) synthesis of the compound represented by [Formula 102]

The compound represented by [Formula 102] was synthesized according to the following [Scheme 10].

[Scheme 10]

6.6 g (15 mmol) of the compound represented by [Formula 1-g] obtained from [Scheme 7], 5.1 g (21 mmol) of the compound represented by [Formula 1-i] obtained from [Scheme 9], Tris ( Dibenzyrideneacetone) 0.3 g (1 mmol) of dipalladium, 0.4 g (2 mmol) of tritertiary butylphosphonium tetrafluoroborate, and 2.9 g (30 mmol) of sodium tertiary butoxide were added to 100 mL of xylene. Stir under reflux for 12 hours. When the reaction is complete, filter under reduced pressure in a hot state. The solution was concentrated under reduced pressure and separated by column chromatography to obtain 7.7 g of a compound represented by Formula 102. (Yield 79.6%)

MS [M] ⁺ 642.19

<Synthesis Example 2> Synthesis of the compound represented by [Formula 18]

(1) Synthesis of the compound represented by [Formula 2-a]

The compound represented by [Formula 2-a] was synthesized according to the following [Scheme 11].

[Scheme 11]

45.1 g of the compound represented by [Formula 2-a] synthesized in the same manner except that 4-bromodibenzothiophene was used instead of 2-bromodibenzothiophene used in [Scheme 1] of <Synthesis Example 1>. got (Yield 75.2%)

(2) Synthesis of the compound represented by [Formula 2-b]

The compound represented by [Formula 2-b] was synthesized according to the following [Reaction Scheme 12].

[Scheme 12]

Except for using [Formula 2-a] instead of [Formula 1-a] used in [Reaction Scheme 2] of <Synthesis Example 1>, 64.7 g of the compound represented by [Formula 2-b] was obtained. . (Yield 87.7%)

(3) Synthesis of the compound represented by [Formula 2-c]

The compound represented by [Formula 2-c] was synthesized according to the following [Scheme 13].

[Scheme 13]

Except for using [Formula 2-b] instead of [Formula 1-b] used in [Scheme 3] of <Synthesis Example 1>, 30.3 g of a compound represented by [Formula 2-c] was obtained. . (Yield 54%)

(4) Synthesis of the compound represented by [Formula 2-d]

The compound represented by [Formula 2-d] was synthesized according to the following [Scheme 14].

[Scheme 14]

[Formula 2-c] was used instead of [Formula 1-c] used in [Reaction Scheme 4] of <Synthesis Example 1>, but 28.7 g of the compound represented by [Formula 2-d] was obtained. . (Yield 74.1%)

(5) Synthesis of the compound represented by [Formula 2-e]

The compound represented by [Formula 2-e] was synthesized according to the following [Scheme 15].

[Scheme 15]

Except for using [Formula 2-d] instead of [Formula 1-d] used in [Scheme 6] of <Synthesis Example 1>, 27.1 g of a compound represented by [Formula 2-e] was obtained. . (Yield 81.2%)

(6) Synthesis of the compound represented by [Formula 2-f]

The compound represented by [Formula 2-f] was synthesized according to the following [Scheme 16].

[Scheme 16]

[Formula 2-e] was used instead of [Formula 1-f] used in [Scheme 7] of <Synthesis Example 1>, but 5.9 g of the compound represented by [Formula 2-f] was obtained through the same synthesis. . (Yield 24.5%)

(7) Synthesis of the compound represented by [Formula 18]

The compound represented by [Formula 18] was synthesized according to the following [Reaction Scheme 17].

[Scheme 17]

5.4 g of a compound represented by [Formula 18] was obtained by synthesizing in the same manner except for using [Formula 2-f] instead of [Formula 1-g] used in [Reaction Scheme 10] of <Synthesis Example 1>. (Yield 62.3%)

MS [M] ⁺ 642.19

<Synthesis Example 3> Synthesis of a compound represented by [Formula 26]

(1) Synthesis of the compound represented by [Formula 3-a]

The compound represented by [Formula 3-a] was synthesized according to the following [Scheme 18].

[Scheme 18]

After dissolving 80.0 g (275 mmol) of dibenzo[d,d]benzo[1,2-b;5,4-b']dithiophene in 800 mL of dimethylformamide in a dried 2L reactor, the mixture is stirred in a nitrogen atmosphere. . The temperature of the reaction solution was lowered to 0° C., and 49.0 g (275 mmol) of N-bromosuccinimide was slowly added dropwise to the reactor, followed by stirring at room temperature for 2 hours. When the reaction was completed, the reaction solution was put into distilled water, and the resulting crystals were filtered and separated by column chromatography to obtain 50.9 g of the compound represented by [Formula 3-a]. (Yield 55.5%)

(2) Synthesis of the compound represented by [Formula 3-b]

The compound represented by [Formula 3-b] was synthesized according to the following [Scheme 19].

[Scheme 19]

[Formula 3-a] was used instead of [Formula 1-d] used in [Reaction Scheme 6] in <Synthesis Example 1>, but 44.3 g of a compound represented by [Formula 3-b] was obtained. . (Yield 78%)

(3) Synthesis of compounds represented by [Formula 3-c] and [Formula 3-d]

Compounds represented by [Formula 3-c] and [Formula 3-d] were synthesized according to the following [Scheme 20].

[Scheme 20]

7.3 g of the compound represented by [Formula 3-c] synthesized in the same manner except for using [Formula 3-b] instead of [Formula 1-f] used in [Scheme 7] of <Synthesis Example 1> 1.9 g of a compound represented by Formula 3-d] was obtained. (Yield 22.6%)

(4) synthesis of the compound represented by [Formula 26]

The compound represented by [Formula 26] was synthesized according to the following [Scheme 21].

[Scheme 21]

7.8 g of a compound represented by [Formula 26] was obtained by synthesizing in the same manner except that [Formula 3-c] was used instead of [Formula 1-g] used in [Reaction Scheme 10] of <Synthesis Example 1>. (Yield 72.5%)

MS [M] ⁺ 583.12

<Synthesis Example 4> Synthesis of a compound represented by [Formula 58]

(1) Synthesis of the compound represented by [Formula 4-a]

The compound represented by [Formula 4-a] was synthesized according to the following [Scheme 22].

[Scheme 22]

After dissolving 70.0 g (241 mmol) of benzo<2,1-b;3,4-b'>bisbenzo<b>thiophene in 560 mL of tetrahydrofuran under nitrogen in a dried 2L reactor, stirring at -78 ° C. While doing so, 211 mL (338 mmol) of 1.6 n-butyllithium was slowly added dropwise. When the dropwise addition is completed, the mixture is stirred at room temperature for 6 hours. Thereafter, 85.7 g (338 mmol) of iodine was slowly added dropwise at -30 °C, and the temperature of the reaction mixture was raised to room temperature and stirred for 6 hours. When the reaction is complete, 500 mL of a saturated solution of sodium thiosulfate pentahydride is added, followed by extraction with ethyl acetate and water. The organic layer was treated with magnesium sulfate to remove moisture, concentrated under reduced pressure, and recrystallized from methylene chloride and heptane to obtain 70.4 g of a compound represented by [Formula 4-a]. (Yield 70.2%)

(2) Synthesis of the compound represented by [Formula 4-b]

The compound represented by [Formula 4-b] was synthesized according to the following [Scheme 23].

[Scheme 23]

[Formula 4-a] was used instead of [Formula 1-d] used in [Scheme 6] of <Synthesis Example 1>, but 60.1 g of the compound represented by [Formula 4-b] was obtained. . (Yield 86.5%)

(3) Synthesis of the compound represented by [Formula 4-c]

The compound represented by [Formula 4-c] was synthesized according to the following [Scheme 24].

[Scheme 24]

[Formula 4-b] was used instead of [Formula 1-f] used in [Scheme 7] of <Synthesis Example 1>, but 22.7 g of a compound represented by [Formula 4-c] was obtained. . (Yield 55.7%)

(4) Synthesis of the compound represented by [Formula 58]

The compound represented by [Formula 58] was synthesized according to the following [Scheme 25].

[Scheme 25]

14.4 g of a compound represented by [Formula 58] was obtained by synthesizing in the same manner except for using [Formula 4-c] instead of [Formula 1-g] used in [Reaction Scheme 10] of <Synthesis Example 1>. (yield 65.3%)

MS [M] ⁺ 583.12

<Synthesis Example 5> Synthesis of a compound represented by [Formula 62]

(1) Synthesis of the compound represented by [Formula 5-a]

The compound represented by [Formula 5-a] was synthesized according to the following [Scheme 26].

[Scheme 26]

[Formula 1-g] used in [Reaction Scheme 10] of <Synthesis Example 1> was synthesized in the same manner except that 2-bromoaniline and [Formula 4-a] were used instead of [Formula 1-i] 23.5 g of a compound represented by Formula 5-a] was obtained. (Yield 78.6%)

(2) Synthesis of the compound represented by [Formula 5-b]

The compound represented by [Formula 5-b] was synthesized according to the following [Scheme 27].

[Scheme 27]

23.5 g (51 mmol) of [Formula 5-a], 2.4 g (2 mmol) of tetrakis(triphenylphosphine)palladium, 10.0 g (102 mmol) of potassium acetate, and 235 mL of dimethylformamide were added to a dried 500 mL reactor. and stirred under reflux for 12 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, poured with distilled water, and the resulting crystals were filtered and separated by column chromatography to obtain 11.2 g of a compound represented by [Formula 5-b]. (Yield 57.7%)

(3) Synthesis of the compound represented by [Formula 62]

The compound represented by [Formula 62] was synthesized according to the following [Scheme 28].

[Scheme 28]

[Formula 1-g] used in [Reaction Scheme 10] of <Synthesis Example 1> was synthesized in the same manner except for using [Formula 5-b] to obtain 11.0 g of a compound represented by [Formula 62]. (Yield 49.7%)

MS [M] ⁺ 583.12

<Synthesis Example 6> Synthesis of a compound represented by [Formula 92]

(1) Synthesis of the compound represented by [Formula 6-a]

The compound represented by [Formula 6-a] was synthesized according to the following [Scheme 29].

[Scheme 29]

52.3 g of the compound represented by [Formula 6-a] was synthesized in the same manner except for using 2-bromodibenzofuran instead of 2-bromodibenzothiophene used in [Scheme 1] of <Synthesis Example 1>. got it (Yield 87.2%)

(2) Synthesis of the compound represented by [Formula 6-b]

The compound represented by [Formula 6-b] was synthesized according to the following [Scheme 30].

[Scheme 30]

Except for using [Formula 6-a] instead of [Formula 1-a] used in [Reaction Scheme 2] of <Synthesis Example 1>, 63.5 g of a compound represented by [Formula 6-b] was obtained. . (Yield 86.1%)

(3) Synthesis of the compound represented by [Formula 6-c]

The compound represented by [Formula 6-c] was synthesized according to the following [Scheme 31].

[Scheme 31]

[Formula 6-b] was used instead of [Formula 1-b] used in [Reaction Scheme 3] of <Synthesis Example 1>, but it was synthesized in the same manner to obtain 33.5 g of a compound represented by [Formula 6-c]. . (Yield 59.8%)

(4) Synthesis of the compound represented by [Formula 6-d]

The compound represented by [Formula 6-d] was synthesized according to the following [Scheme 32].

[Scheme 32]

Except for using [Formula 6-c] instead of [Formula 1-c] used in [Reaction Scheme 3] of <Synthesis Example 1>, 32.6 g of a compound represented by [Formula 6-d] was obtained. . (Yield 84.1%)

(5) Synthesis of the compound represented by [Formula 6-e]

The compound represented by [Formula 6-e] was synthesized according to the following [Scheme 33].

[Scheme 33]

Except for using [Formula 6-d] instead of [Formula 1-d] used in [Scheme 6] of <Synthesis Example 1>, 27.7 g of a compound represented by [Formula 6-e] was obtained. . (Yield 82.9%)

(6) Synthesis of compounds represented by [Formula 6-f] and [Formula 6-g]

Compounds represented by [Formula 6-f] and [Formula 6-g] were synthesized according to the following [Scheme 34].

[Scheme 34]

6.6 g of the compound represented by [Formula 6-f] synthesized in the same manner except for using [Formula 6-e] instead of [Formula 1-f] used in [Scheme 7] of <Synthesis Example 1> 1.5 g of a compound represented by Chemical Formula 6-g] was obtained. (Yield 19.9%)

(7) synthesis of the compound represented by [Formula 92]

The compound represented by [Formula 92] was synthesized according to the following [Scheme 35].

[Scheme 35]

[Formula 6-f] was used instead of [Formula 1-g] used in [Reaction Scheme 10] of <Synthesis Example 1>, but 8.1 g of a compound represented by [Formula 92] was obtained. (Yield 36.6%)

MS [M] ⁺ 626.21

<Synthesis Example 7> Synthesis of a compound represented by [Formula 124]

(1) Synthesis of the compound represented by [Formula 7-a]

The compound represented by [Formula 7-a] was synthesized according to the following [Scheme 36].

[Scheme 36]

[Formula 3-a] used in [Scheme 18] of <Synthesis Example 3> was synthesized in the same manner except that benzo<1,2-b;4,3-b'>bisbenzofuran was used instead of [Formula 3-a] 7-a] to obtain 44.3 g of the compound. (Yield 78%)

(2) Synthesis of the compound represented by [Formula 7-b]

The compound represented by [Formula 7-b] was synthesized according to the following [Scheme 37].

[Scheme 37]

[Formula 7-a] was used instead of [Formula 1-d] used in [Reaction Scheme 6] of <Synthesis Example 1>, but 55.6 g of a compound represented by [Formula 7-b] was obtained through the same synthesis. . (Yield 80.0%)

(3) Synthesis of the compound represented by [Formula 7-c]

The compound represented by [Formula 7-c] was synthesized according to the following [Scheme 38].

[Scheme 38]

[Formula 7-b] was used instead of [Formula 1-f] used in [Reaction Scheme 7] of <Synthesis Example 1>, but 23.5 g of a compound represented by [Formula 7-c] was obtained through the same synthesis. . (Yield 57.7%)

(4) synthesis of the compound represented by [Formula 124]

The compound represented by [Formula 124] was synthesized according to the following [Scheme 39].

[Scheme 39]

[Formula 1-g] used in [Reaction Scheme 10] of <Synthesis Example 1> was synthesized in the same manner except for using [Formula 7-c] to obtain 6.4 g of a compound represented by [Formula 124]. (Yield 29.0%)

MS [M] ⁺ 551.16

Example: Manufacturing of Organic Light-Emitting Diodes

After the ITO glass was patterned so that the light emitting area had a size of 2 mm × 2 mm, it was cleaned. After the substrate is mounted in a vacuum chamber, the base pressure is set to 1 × 10 ^-6 torr, and organic materials are formed on the ITO in the order of DNTPD (700 Å) and NPD (300 Å). Then, the compound prepared by the present invention + RD-1 (10%) (300 Å), compound E: Liq = 1: 1 (250 Å), Liq (10 Å), Al (1,000 Å), in order of deposition and measured at 0.4 mA. The structures of DNTPD, NPD, RD-1, compound E, and Liq are as follows.

Comparative Example 1: Manufacturing of organic light emitting diode

An organic light emitting diode device for comparative example was manufactured in the same manner except for using BAlq, which is generally known as a phosphorescent host material, instead of the compound prepared by the invention in the device structure of the above example, and the structure of BAlq is as follows.

Voltage, current density, luminance, color coordinates, and lifetime of the organic light emitting device manufactured according to Examples 1 to 7 and Comparative Example 1 were measured, and the results are shown in [Table 1]. T95 means the time required for the luminance to decrease to 95% compared to the initial luminance (3000 cd/m 2 ).

division host Doping concentration % V Cd/㎡ CIEx CIEy T ₉₅ (Hr) Comparative Example 1 BAlq 10 6.2 1470 0.665 0.335 40 Example 1 Formula 102 10 4.5 1580 0.665 0.335 145 Example 2 Formula 18 10 4.4 1550 0.664 0.336 230 Example 3 Formula 26 10 4.2 1580 0.665 0.335 205 Example 4 Formula 58 10 4.4 1590 0.665 0.335 175 Example 5 Formula 62 10 4.3 1560 0.664 0.336 120 Example 6 Formula 92 10 4.5 1600 0.664 0.336 250 Example 7 Formula 124 10 4.4 1580 0.664 0.336 150

As shown in [Table 1], the device employing the organic light emitting compound according to the present invention has superior luminous efficiency and significantly lower driving voltage than the organic electroluminescent device employing BAlq, which is known as a conventional phosphorescent host material. It can be seen that it has a low and excellent long life.

Claims (8)

An organic light-emitting compound represented by the following [Formula 1]:
[Formula 1]

In the above [Formula 1],
A1 And A2 are the same as or different from each other, and each independently represents a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 carbon atoms,
X ₁ is S or O;
X ₂ and X ₃ are the same as or different from each other, and are each independently any one selected from S, O, and NR ₁ ,
At least one of X ₂ and X ₃ is NR ₁ , except when X ₂ and X ₃ are NR ₁ at the same time;
A plurality of Y and Z are each CR, wherein R is hydrogen,
Two adjacent Ys among the plurality of Ys combine with '*' of Q1 to form a condensed ring, and two adjacent Zs among the plurality of Zs combine with '*' of Q2 to form a condensed ring,
R ₁ is any one selected from a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms and a substituted or unsubstituted heteroaryl group having 8 to 10 carbon atoms;
'Substitution' in 'substituted or unsubstituted' is substituted with one or more substituents selected from the group consisting of heavy hydrogen, an alkyl group having 1 to 24 carbon atoms, an aryl group having 6 to 24 carbon atoms, and a heteroaryl group having 2 to 24 carbon atoms. means that,
The compound represented by [Formula 1] excludes the compound having the following structure.

According to claim 1,
In [Formula 1], A1 and A2 are organic light emitting compounds, characterized in that a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 18 carbon atoms. According to claim 1,
The organic light emitting compound represented by [Formula 1] is characterized in that selected from compounds represented by the following formula:

An organic electroluminescent device comprising a first electrode, a second electrode, and one or more organic material layers disposed between the first electrode and the second electrode,
An organic electroluminescent device characterized in that at least one layer of the organic material layer contains the organic light emitting compound of [Chemical Formula 1] according to claim 1. According to claim 4,
The organic material layer includes at least one layer of a hole injection layer, a hole transport layer, and a layer that simultaneously injects and transports holes,
An organic electroluminescent device, characterized in that at least one of the layers includes the organic light emitting compound represented by the [Chemical Formula 1]. According to claim 4,
The organic electroluminescent device, wherein the organic material layer includes a light emitting layer, and the light emitting layer includes an organic light emitting compound represented by the [Chemical Formula 1]. According to claim 6,
The organic electroluminescent compound represented by [Chemical Formula 1] is used as a host compound in the light emitting layer. According to claim 4,
An organic electroluminescent device characterized in that it emits white light by further including at least one organic light emitting layer emitting red, green or blue light in the organic material layer.

Images