KR102173481B1 - New organic electroluminescent compound and organic electroluminescent device comprising the same - Google Patents

Abstract

The present invention relates to a novel organic light-emitting compound and an organic light-emitting device comprising the same, and when the compound according to the present invention is used as a host material in a phosphorescent light-emitting layer, an organic light-emitting device having excellent light-emitting characteristics such as driving voltage, luminance, and long life is provided. Can be implemented.

Description

A novel organic electroluminescent compound and an organic electroluminescent device comprising the same

The present invention relates to a novel phosphorescent host compound, an organic light-emitting compound, and an organic light-emitting device including the same.

An organic light-emitting device is a device that emits light while electrons and holes form a pair and then disappear when charge is injected into an organic film formed between an electron injection electrode (cathode) and a hole injection electrode (anode). Not only can the device be formed on a flexible transparent substrate such as plastic, but it can be driven at a lower voltage (less than 10V) compared to a plasma display panel or an inorganic EL display, and also consumes power. It is relatively small and has the advantage of excellent color.

Typical organic light emitting devices include a substrate, an anode, a hole injection layer that accepts holes from the anode, a hole transport layer that transports holes, a light emitting layer that emits light by combining holes and electrons, an electron transport layer that receives electrons from the cathode and transfers them to the light emitting layer, And a cathode. In some cases, a light-emitting layer may be formed by doping a small amount of fluorescent or phosphorescent dye on the electron transport layer or hole transport layer without a separate light-emitting layer. In the case of using a polymer, the hole transport layer, the light-emitting layer, and the electron transport layer are generally used. Of the polymers can be carried out simultaneously. The organic thin film layers between the two electrodes are formed by vacuum deposition, spin coating, inkjet printing, roll coating, or the like, and a separate electron injection layer is sometimes inserted for efficient injection of electrons from the cathode.

The most important factor determining luminous efficiency in an organic light-emitting device is a light-emitting material. Currently, a fluorescent material is widely used as a light-emitting material, but the development of a phosphorescent material is one of the best ways to theoretically improve light-emitting efficiency up to four times. Until now, iridium (III) complex series are widely known as phosphorescent materials, and materials such as (acac)Ir(btp) ₂ , Ir(ppy) ₃ and Firpic are known for each RGB. CBP is the most widely known phosphorescent host material so far, and high-efficiency OLEDs with hole blocking layers such as BCP and BAlq are known, and pioneers of Japan have developed high-performance OLEDs using BAlq derivatives as hosts. There is a bar.

However, organic electroluminescent devices using conventional phosphorescent materials have significantly higher current efficiency (cd/A) than devices using fluorescent materials, but when materials such as BAlq and CBP are used as a host of phosphorescent materials, fluorescent materials There is no significant advantage in terms of power efficiency (lm/w) because the driving voltage is higher than that of the device using the device, and the development of a more stable and high-performance host material is required because it is not at a satisfactory level in terms of device life. .

Accordingly, the present inventors have repeatedly studied the light-emitting host material in consideration of the problems of the prior art, and as a result, organic light-emitting compounds, which are novel phosphorescent host compounds that can greatly improve luminous efficiency, stability, and device life, and organic light-emitting compounds using the same The present invention was completed to provide a device.

KR 10-2016-0017055 A

An object of the present invention is to provide a novel phosphorescent host compound, an organic light emitting compound.

In addition, the present invention provides an organic light-emitting device with improved power consumption by inducing an increase in power efficiency and quantum efficiency by using the organic light-emitting compound as a phosphorescent host material, which not only has excellent light emission characteristics, but also enhances the driving voltage. There is a purpose.

The present invention relates to a novel organic light-emitting compound and an organic light-emitting device including the same, and more specifically, two carbazoles have a skeleton fused to both sides of a five-membered ring, and the nitrogen atom of one carbazole moiety Uracil is bonded to the terminal, and aryl or heteroaryl substituted with a nitrogen atom of the other carbazole is bonded to the organic light-emitting compound of a novel structure capable of deposition or solution process, and an organic light-emitting device including the same About.

The present invention provides an organic light emitting compound represented by the following formula (1).

[Formula 1]

In Formula 1,

L ₁ is C1-C30 alkylene;

X ₁ is NR', O or S;

R'is hydrogen, deuterium, halogen, C1-C30 alkyl, C3-C30 cycloalkyl, C6-C30 aryl or C3-C30 heteroaryl;

m is an integer from 1 to 3;

Q is NR ₁ , O, S or CR ₂ R ₃ ;

R ₁ to R ₃ are each independently hydrogen, deuterium, halogen, C1-C30 alkyl, C3-C30 cycloalkyl, C6-C30 aryl or C3-C30 heteroaryl;

L ₂ and L ₃ are each independently C6-C30 arylene or C3-C30 heteroarylene;

Ar ₁ is C6-C30 aryl or C3-C30 heteroaryl;

The aryl or heteroaryl of Ar ₁ is C1-C30 alkyl, halo C1-C30 alkyl, halogen, cyano, C3-C30 cycloalkyl, C3-C30 heterocycloalkyl, C1-C30 alkoxy, C6-C30 aryloxy, C6 -C30 aryl C1-C30 alkyl, C6-C30 aryl, C3-C30 heteroaryl, mono or diC1-C30 alkylamino, mono or diC6-C30 arylamino, triC1-C30 alkylsilyl, diC1-C30 alkyl C6 -C30 arylsilyl, triC6-C30 arylsilyl, may be further substituted with one or more selected from the group consisting of nitro and hydroxy;

The heteroaryl and heteroarylene include one or more heteroatoms selected from B, N, O, S, P(=O), Si and P.

In addition, the present invention provides an organic light-emitting device including the organic light-emitting compound represented by Formula 1 above.

The compound according to the present invention has a skeleton in which two carbazoles are fused to both sides of a five-membered ring, uracil is bonded to the end of the nitrogen atom of one carbazole portion, and nitrogen of the other carbazole portion. An organic light-emitting compound of a novel structure in which an atom-substituted aryl or heteroaryl is bonded and capable of deposition or solution process. When included in the emission layer of an organic light-emitting device as a host material, specifically a phosphorescent host material, luminous efficiency, global efficiency , Quantum efficiency and device life are good, and it shows an appropriate color coordinate.

In addition, the organic light-emitting compound according to the present invention has improved solubility and heat resistance in various organic solvents, specifically halogen-substituted or non-substituted hydrocarbon-based organic solvents. This is possible.

In addition, the organic light-emitting compound according to the present invention has high electron transfer efficiency, so it not only prevents crystallization during device fabrication, but also improves the current characteristics of the device due to good layer formation and enhances the driving voltage, leading to an increase in power efficiency and consumption. There is an advantage of manufacturing an organic light-emitting device with improved power.

The organic light-emitting compound, which is a novel phosphorescent host compound according to the present invention, and the organic light-emitting device using the same are described below. Descriptions of known functions and configurations that may unnecessarily obscure the subject matter of the present invention in the following description will be omitted.

As used herein, the term “alkyl”, “alkoxy” and other substituents including “alkyl” moieties include all linear or branched forms. In addition, as for the substituents including alkyl, alkoxy and other alkyl moieties according to the present invention, a short-chain substituent having 1 to 7 carbon atoms takes precedence, but it is a matter of course that a long-chain substituent of 8 or more is also an aspect of the present invention.

In addition, the term "aryl" in the present specification is an organic radical derived from an aromatic hydrocarbon by the removal of one hydrogen, suitably containing 4 to 7, preferably 5 or 6 ring atoms in each ring or It includes a fused ring system, and includes a form in which a plurality of aryls are connected by a single bond. Specific examples include phenyl, naphthyl, biphenyl, terphenyl, anthryl, indenyl, fluorenyl, phenanthryl, triphenylenyl, pyrenyl, peryleneyl, chrysenyl, naphthyl, fluoranthenyl, etc. , Is not limited thereto.

In addition, the term "arylene" in the present specification refers to a divalent organic radical induced by the removal of one hydrogen from the aryl, and follows the definition of the aryl.

In addition, the term "heteroaryl" in the present specification includes 1 to 4 heteroatoms selected from B, N, O, S. P(=O), Si and P as an aromatic ring skeleton atom, and the rest of the aromatic ring skeleton It means an aryl group whose atom is carbon, and is a 5 to 6 membered monocyclic heteroaryl, and a polycyclic heteroaryl condensed with one or more benzene rings, and may be partially saturated. In addition, the heteroaryl in the present invention also includes a form in which one or more heteroaryls are linked by a single bond. Specific examples include furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, isoxazolyl, oxazolyl, triazinyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, etc. Monocyclic heteroaryl of; Benzofuranyl, benzothiophenyl, isobenzofuranyl, benzoimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzoxazolyl, isoindolyl, indolyl, indazolyl, quinolyl, iso Polycyclic heteroaryl such as quinolyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, and benzocarbazolyl; Including, but not limited to.

In addition, the term "heteroarylene" used herein refers to a divalent organic radical induced by the removal of one hydrogen from the heteroaryl, and follows the definition of the heteroaryl.

In addition, the term “cycloalkyl” as used herein refers to a fully saturated or partially unsaturated hydrocarbon ring of carbon atoms, and includes fused cyclic, bridged cyclic and spirocyclic groups. Examples of cycloalkyl are cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, decalin, bike[3.1.1]heptane, bicyclo[2.2.1]heptane, bicyclo[2.2.2]octane, and bike[ 3.2.2] Nonane, spiro [2.5] octane, spiro [3.5] nonane, adamantyl, etc. are included, but are not limited thereto.

In addition, the term "heterocycloalkyl" in the present specification includes 1 to 4 heteroatoms selected from B, N, O, S. P(=O), Si and P as an alicyclic ring skeleton atom, and the remaining alicyclic It means a cycloalkyl group in which the group ring skeleton atom is carbon, and includes monocyclic or polycyclic cases.

In addition, the term "halogen" in the present specification means a fluorine (F), chlorine (Cl), bromine (Br) or iodine (I) atom.

In addition, in the present specification, the number of carbon atoms according to the definition of the substituent described in Formula 1 does not include the number of carbon atoms of the substituent that may be further substituted.

The phosphorescent host compound according to the present invention may be represented by the following formula (1).

[Formula 1]

In Formula 1,

L ₁ is C1-C30 alkylene;

X ₁ is NR', O or S;

R'is hydrogen, deuterium, halogen, C1-C30 alkyl, C3-C30 cycloalkyl, C6-C30 aryl or C3-C30 heteroaryl;

m is an integer from 1 to 3;

Q is NR ₁ , O, S or CR ₂ R ₃ ;

R ₁ to R ₃ are each independently hydrogen, deuterium, halogen, C1-C30 alkyl, C3-C30 cycloalkyl, C6-C30 aryl or C3-C30 heteroaryl;

L ₂ and L ₃ are each independently C6-C30 arylene or C3-C30 heteroarylene;

Ar ₁ is C6-C30 aryl or C3-C30 heteroaryl;

The aryl or heteroaryl of Ar ₁ is C1-C30 alkyl, halo C1-C30 alkyl, halogen, cyano, C3-C30 cycloalkyl, C3-C30 heterocycloalkyl, C1-C30 alkoxy, C6-C30 aryloxy, C6 -C30 aryl C1-C30 alkyl, C6-C30 aryl, C3-C30 heteroaryl, mono or diC1-C30 alkylamino, mono or diC6-C30 arylamino, triC1-C30 alkylsilyl, diC1-C30 alkyl C6 -C30 arylsilyl, triC6-C30 arylsilyl, may be further substituted with one or more selected from the group consisting of nitro and hydroxy;

The heteroaryl and heteroarylene include one or more heteroatoms selected from B, N, O, S, P(=O), Si and P.

The organic light-emitting compound of Formula 1 has a skeleton in which two carbazoles are fused to both sides of a 5-membered ring, uracil is bonded to the end of the nitrogen atom of one carbazole portion, and the other carbazole portion It is a structure in which a substituted aryl or heteroaryl is bonded to the nitrogen atom of, and is chemically stable and has high electron density, so that the luminous efficiency is high.

In addition, the organic light-emitting compound of Formula 1 has excellent solubility in various organic solvents such as a halogenated solvent and an environment-friendly halogen-free solvent, so that an organic light-emitting device can be manufactured by a solution process, thereby maintaining a large emission area. Not only that, but also the improved heat resistance and interface properties with the electrode are very excellent.

In the organic light-emitting compound according to an embodiment of the present invention, in terms of implementing excellent luminous efficiency and improved driving life, Q may be O or S.

In the organic light emitting compound according to an embodiment of the present invention, in terms of implementing more excellent efficiency (eg, luminous efficiency, global efficiency, quantum efficiency, etc.), L ₂ and L ₃ are each independently C6-C12 arylene. May be, preferably phenylene or biphenylene.

The organic light emitting compound according to an embodiment of the present invention may be specifically represented by Formula 2 below in terms of implementing excellent chemical and electrical stability, luminous efficiency, power efficiency, quantum efficiency, and improved driving life.

[Formula 2]

In Chemical Formula 2,

L ₁ is C1-C20 alkylene;

X ₁ is O or S;

m is an integer from 1 to 3;

Q is O or S;

Ar ₁ is C6-C20 aryl or C3-C20 heteroaryl;

The aryl or heteroaryl of Ar ₁ is C1-C20 alkyl, halo C1-C20 alkyl, halogen, cyano, C3-C20 cycloalkyl, C6-C20 aryl C1-C20 alkyl, C6-C20 aryl and C3-C20 heteroaryl It may be further substituted with one or more selected from the group consisting of.

,

또는

일 수 있고, A고리 및 B고리는 각각 독립적으로 단일환 또는 다환의 방향족 고리이고; Y₁ 및 Y₃는 각각 독립적으로 CR₁₁R₁₂, NR₁₃, S 또는 O이고; Y₂은 단일결합, CR₁₄R_15, NR₁₆, S 또는 O이고; R₁₁ 내지 R₁₆은 각각 독립적으로 C1-C20알킬, C6-C20아릴 또는 C3-C20헤테로아릴일 수 있다.In the organic light-emitting compound according to an embodiment of the present invention, Ar ₁ is more preferably

,

or

And ring A and ring B are each independently a monocyclic or polycyclic aromatic ring; Y ₁ and Y ₃ are each independently CR ₁₁ R ₁₂ , NR ₁₃ , S or O; Y ₂ is a single bond, CR ₁₄ R _15, NR ₁₆ , S or O; R ₁₁ to R ₁₆ may each independently be C1-C20 alkyl, C6-C20 aryl or C3-C20 heteroaryl.

In the organic light emitting compound according to an embodiment of the present invention, the A ring and the B ring may each independently be benzene or naphthalene.

The organic light-emitting compound according to an embodiment of the present invention may be preferably one represented by Formula 3 below in terms of implementing better chemical and electrical stability, luminous efficiency, power efficiency, quantum efficiency, and improved driving life.

[Formula 3]

In Chemical Formula 3,

n is an integer from 1 to 10;

m is an integer of 1 or 2;

Ar ₁ is selected from the following structures;

Y is CR ^a R ^b , NR ^c , S or O;

R ^a , R ^b , R ^c , R ₁₁ to R ₁₅ , R ₁₇ and R ₁₈ are each independently C1-C10 alkyl, C6-C12 aryl or C3-C12 heteroaryl.

,

,

또는

이고; Y은 CR^aR^b, NR^c, S 또는 O이고; R^a, R^b, R^c, R₁₇ 및 R₁₈은 각각 독립적으로 C1-C7알킬 또는 C6-C12아릴일 수 있다.In the organic light-emitting compound represented by Formula 3 according to an embodiment of the present invention, more preferably in terms of improving the efficiency of the device, such as improved electron mobility and current efficiency, luminous efficiency, and improved driving life, n is 1 Is an integer of 5; m is an integer of 1 or 2; Ar ₁ is

,

,

or

ego; Y is CR ^a R ^b , NR ^c , S or O; R ^a , R ^b , R ^c , R ₁₇ and R ₁₈ may each independently be C1-C7 alkyl or C6-C12 aryl.

,

또는

이고; Y은 CR^aR^b, NR^c, S 또는 O이고; R^a, R^b 및 R^c은 각각 독립적으로 C1-C7알킬 또는 C6-C12아릴일 수 있다.In the organic light-emitting compound represented by Formula 3 according to an embodiment of the present invention, more preferably in terms of improving the efficiency of the device, such as improved electron mobility and current efficiency, luminous efficiency, and improved driving life, n is 2 Is an integer of 4; m is an integer of 1 or 2; Ar ₁ is

,

or

ego; Y is CR ^a R ^b , NR ^c , S or O; R ^a , R ^b and R ^c may each independently be C1-C7 alkyl or C6-C12 aryl.

는 L₂의 메타(meta) 위치, 바람직하게는 L₂가 C6-C30아릴렌이고 상기 아릴렌의 메타 위치에

이 하나 또는 둘 치환될 수 있다.In the organic light-emitting compound according to an embodiment of the present invention, the

Is in the meta (meta) position, preferably, L ₂ is C6-C30 arylene is meta-position of the arylene group of L ₂

One or two of these can be substituted.

The organic light-emitting compound according to an embodiment of the present invention may be more preferably represented by the following Formula 4 or Formula 5 in terms of implementing better chemical and electrical stability, luminous efficiency, power efficiency, quantum efficiency, and improved driving life. have.

[Formula 4]

[Formula 5]

In Formulas 4 and 5, n and Ar ₁ are the same as defined in Formula 3.

The organic light-emitting compound according to an exemplary embodiment of the present invention may be used in an organic material layer of an organic light-emitting device due to its structural specificity, and specifically, may be used as a host compound in the light-emitting layer in the organic material layer. More specifically, the organic light emitting compound according to an embodiment of the present invention may be used as a phosphorescent host compound in the light emitting layer in the organic material layer.

The organic light-emitting compound according to an embodiment of the present invention may be more specifically exemplified by compounds having the following structures, but is not limited thereto.

The compound according to the present invention may be prepared as shown in the following reaction scheme, but is not limited thereto, and of course, it may be prepared through a known organic reaction.

[Scheme 1]

In Scheme 1, L ₁ , X ₁ , L ₂ , L ₃ , m, Q and Ar ₁ are the same as defined in Formula 1; Hal is a halogen.

In addition, the present invention provides an organic light-emitting device including the compound of Formula 1.

An organic light-emitting device according to an embodiment of the present invention includes a first electrode; A second electrode; And one or more organic material layers interposed between the first electrode and the second electrode. The organic material layer may have a single-layer structure consisting of one layer, or a multi-layer structure of two or more layers including a light emitting layer. When the organic material layer of the organic light emitting device has a multilayer structure, it may be a structure in which, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and the like are stacked. However, the structure of the organic light-emitting device is not limited thereto, and may include a smaller number of organic material layers.

The organic material layer may include an emission layer including the compound of Formula 1, and the compound of Formula 1 may be included as a phosphorescent host material in the emission layer. When the compound of Formula 1 is included as a host material in the emission layer, the emission layer may include at least one dopant.

The first electrode may be an anode layer, and is an electrode for injecting holes into the hole injection layer. Therefore, the material for forming the anode layer is not limited as long as the properties are imparted to the anode layer. Specific examples of the material for forming the anode layer include metals such as vanadium, chromium, copper, zinc, gold, or alloys thereof, zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO), and Metal oxides such as ZnO:Al or SnO2:Sb combination of metals and oxides, poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene](PEDT) , Polypyrrole and conductive polymers such as polyaniline, but are not limited thereto. In addition, the anode layer may be formed of only one type of the above-described materials or may be formed of a mixture of a plurality of materials, and a multi-layered structure composed of a plurality of layers having the same composition or different composition may be formed.

The organic material layer according to an embodiment of the present invention may include a hole injection layer (HIL), a hole blocking layer (HBL), a hole transport layer (HTL), a light emitting layer, an electron transport layer (ETL), an electron injection layer (EIL), and the like. And can be omitted if necessary. The organic material layer may be formed by a vacuum deposition method or a solution coating method. Examples of the solution coating method include, but are not limited to, spin coating, dip coating, doctor blading, inkjet printing, or thermal transfer method.

The hole injection layer (HIL) may be formed on the first electrode by using various methods such as a vacuum deposition method, a spin coating method, a cast method, and a Langmuir-Blodgett (LB) method. Materials include CuPc (copper phthalocyanine), NPD (N,N'-dinaphthyl-N,N'-phenyl-(1,1'-biphenyl)-4,4'-diamine), m-MTDATA (4,4' ,4"-tris(3-Methylphenylphenylamino)triphenylamine), 1-TNATA (4,4',4"-tris[1-naphthyl(phenyl)amino]triphenylamine), 2-TNATA (4,4',4"- Aromatic amines such as tris[2-naphthyl(phenyl)amino]triphenylamine), p-DPA-TDAB (1,3,5-tris[N-(4-diphenylaminophenyl)phenylamino]benzene), and polythiophene derivatives as conductive polymers Phosphorus poly(3,4-ethylenedioxythiophene)-poly(styrnesulfonate) (PEDOT:PSS), etc. In the embodiment of the present invention, PEDOT:PSS was used as a hole injection layer, and the hole injection layer was 10 to 60 nm It may be coated on the top of the first electrode with a thickness of.

In addition, the hole transport layer (HTL) is formed on the top of the hole injection layer by using various methods such as vacuum deposition, spin coating, cast method, and LB method to stably supply holes introduced through the hole injection layer to the light emitting layer. I can. As a material for the hole transport layer that can be used, a material that is commonly used can be used, and preferably NPB (N,N'-bis(naphthalen-1-yl)-N,N'-bis(phenyl)-benzidine) , NPD (N,N'-bis(naphthalen-1-yl)-N,N'-bis(phenyl)-2,2'-dimethylbenzidine), mCP (1,3-Bis(N-carbazolyl)benzene), TPD (N,N'-Bis(3-methylphenyl)-N,N'-diphenylbenzidine), TTB (N,N,N',N'-tetrakis(4-methylphenyl)-(1,1'-biphenyl)- 4,4-diamine), TTP (N1,N4-diphenyl-N1,N4-dim-tolylbenzene-1,4-diamine), ETPD (N,N'-bis(4-methylphenyl)-N,N'-bis (4-ethylphenyl)-[1,1'-(3,3'-dimethyl)biphenyl]-4,4'-diamine), VNPB (N4,N4'-di(naphthalen-1-yl)-N4,N4 '-bis(4-vinylphenyl)biphenyl-4,4'-diamine), ONPB (N4,N4'-bis(4-(6-((3-ethyloxetan-3-yl)methoxy)hexyl)phenyl)-N4 ,N4'-diphenylbiphenyl-4,4'-diamine), OTPD (N4,N4'-bis(4-(6-((3-ethyloxetan-3-yl)methoxy)hexyl)phenyl)-N4,N4'- diphenylbiphenyl-4,4'-diamine), etc.; Polymeric hole transport materials such as PVK (poly-N-vinylcarbazole), polyaniline, and (phenylmenyl) polysilane may be used. Preferably, NPD, mCP or PVK may be used, and PVK was used as the hole transport layer in the embodiment of the present invention, and the hole transport layer may be stacked on top of the light emitting layer with a thickness of 10 to 60 nm.

The emission layer according to an exemplary embodiment of the present invention may be a phosphorescent emission layer, and by including the compound of Formula 1 according to the present disclosure, an organic light emitting device having high luminance and long lifespan characteristics may be implemented. In the light-emitting layer of the organic light-emitting device of the present invention, the film thickness of the light-emitting layer is not limited, but from the viewpoint of uniformity of the film, application of unnecessary high voltage during light emission, and improvement of the stability of light emission color against a driving current, 2 It can be adjusted in the range of nm to 5 μm, can be adjusted in the range of 5 to 50 nm, or can be adjusted in the range of 10 to 40 nm.

In addition, the light-emitting layer can obtain a color of high luminance with higher efficiency by using a phosphorescent dopant together. In this case, the used dopant is not limited, and a known dopant may be selected and used as necessary. The phosphorescent dopant is a compound capable of emitting light from triplet excitons, and is not particularly limited as long as it emits light from triplet excitons. A specific example may be a metal complex including one or more metals selected from the group consisting of Ir, Ru, Pd, Pt, Os, and Re, and may be a porphyrin metal complex or an ortho metallized metal complex.

The porphyrin metal complex may be specifically a porphyrin platinum complex.

The ortho-metallized metal complex is a 2-phenylpyridine (ppy) derivative, a 7,8-benzoquinoline derivative, a 2-(2-thienyl)pyridine (2-(2-thienyl)pyridine, tp) derivative , 2-(1-naphthyl)pyridine (2-(1-naphthyl)pyridine, npy) derivatives, 2-phenylquinoline (2-phenylquinoline, pq) derivatives, etc. may be included as a ligand. E?, these derivatives may have a substituent as necessary. As an auxiliary ligand, it may further have a ligand other than the above ligand such as acetylacetonato (acac) and picric acid. Specific examples include bisthienylpyridine acetylacetonate Iridium, bis(2-benzo[b]thiophen-2-yl-pyridine)(acetylacetonato)iridium(III) (bis(2- benzo[b]thiophen-2-yl-pyridine)(acetylacetonato)iridium(III), Ir(btp) ₂ (acac)), bis(2-phenylbenzothiazole)(acetylacetonato)iridium(III) ( bis(2-phenylbenzothiazole)(acetylacetonato)iridium(III), Ir(bt) ₂ (acac)), bis(1-phenylisoquinoline)(acetylacetonato)iridium(III) (bis(1-phenylisoquinoline)( acetylacetonato)Iridium(III), Ir(piq) ₂ (acac)), tris(1-phenylisoquinoline) iridium(III) (tris(1-phenylisoquinoline)iridium(III), Ir(piq) ₃ ), tris( 2-phenylpyridine) iridium (III) (tris (2-phenylpyridine) iridium (III), Ir (ppy) ₃ ), tris (2-biphenylpyridine) iridium (tris (2-biphenylpyridine) iridium), tris (3 -Biphenylpyridine) iridium (tris (3-biphenylpyridine) iridium), tris (4-biphenylpyridine) iridium (tris (4-biphenylpyridine) iridium), and the like, but are not limited thereto.

The amount of the dopant included in the emission layer is not limited, but as an example, it may be included in the range of 2 to 20 parts by weight based on 100 parts by weight of the host material (compound of Formula 1), and the total content of the dopant relative to the total weight of the emission layer is It may be in the range of 0.5 to 35% by weight.

In this case, a hole blocking layer (HBL) may be formed to prevent diffusion of triplet excitons or holes into the electron transport layer. In the case of forming the hole blocking layer by vacuum evaporation and spin coating, the conditions vary depending on the compound to be used, but may generally be within the same range of conditions as the hole injection layer. A known hole-blocking material can also be used, and examples thereof include an oxadiazole derivative, a triazole derivative, and a phenanthroline derivative. As a more specific example, BCP or the like may be used as a material for the hole blocking layer.

The electron transport layer (ETL) is mainly composed of a material containing a chemical component that attracts electrons. For this purpose, high electron mobility is required, and electrons are stably supplied to the light emitting layer through smooth electron transport. As the material of the electron transport layer that can be used in accordance with the present invention, a material that is commonly used may be used, preferably TSPO1 (diphenyl[4-(triphenylsilyl)phenyl]phosphine oxide), TPBI (1,3,5-tris (N-phenylbenzimidazol-2-yl)benzene); Alq ₃ (tris(8-hydroxyquinolinato)aluminum); BCP (2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline); PBD (2-(4-biphenyl)-5-(4-tert-butyl-phenyl)-1,3,4-oxadizole), TAZ (3-(4-biphenyl)-4-phenyl-5-(4- tert-butyl-phenyl)-1,2,4-triazole), OXD-7 (1,3-bis[2-(4-tert-butylphenyl)-1,3,4-oxadiazo-5-yl]benzene) Azole compounds such as; tris(phenylquinoxaline) (TPQ); TmPyPB (3,3'-[5'-[3-(3-Pyridinyl)phenyl][1,1':3',1''-terphenyl]-3,3''-diyl]bispyridine) etc. However, it is not limited thereto. Preferably, TSPO1, TPBi or Alq3 may be used, and TSPO1 and TPBi were used as electron transport layers in an embodiment of the present invention, and the electron transport layer may be stacked on top of the emission layer with a thickness of 5 to 150 nm.

In addition, the electron injection layer may be deposited to a thickness of 1 to 50 nm using LIF or lithium quinolate (Liq), but is not limited thereto.

In addition, the second electrode may be a negative electrode layer, and a specific example is a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or an alloy thereof, LiF/ A metal having a low work function, such as a multi-layered material such as Al or LiO2/Al, may be used, and more specifically, Al is preferred.

The organic light-emitting device according to the present invention exhibits an efficient host-dopant energy transfer mechanism, and thus can exhibit a reliable high-efficiency light-emitting characteristic based on an effect of improving electron density distribution. In addition, it is possible to secure high-performance light-emitting characteristics having high efficiency and long life in each color by overcoming the initial efficiency lowering characteristics and low life characteristics of existing materials.

The organic light-emitting device according to the present invention described above may be applied to a display device, and the display device may be a display device using a backlight unit, and the organic light-emitting device may be used as a light source and a single light source of a backlight unit. The display device may be an organic electroluminescent display (OLED), but is not limited thereto.

In the following, for a detailed understanding of the present invention, an organic light-emitting compound according to the present invention, a method of manufacturing the same, and luminescence characteristics of the device are described with reference to the representative compound of the present invention, and the following examples are for illustrative purposes of the present invention. It is not intended to limit the scope of protection of the present invention.

[Production Example 1] Preparation of Compound A

Preparation of compound a-1

Dibenzofuran (150 g, 0.891 mol) was put in a 2000 mL 3-neck round bottom flask under nitrogen, and anhydrous tetrahydrofuran (1000 mL) was added, followed by cooling to -78 °C or less. After slowly subdividing and adding n-butyllithium (926.9 g, 5.71 mol), the mixture was maintained at a low temperature for about 30 minutes, and stirred at room temperature for 17 hours. After the reaction was cooled to -78 °C or lower, triisopropylborate (369 g, 1.962 mol) was added, stirred at room temperature for 6 hours, and 2N hydrochloric acid was slowly added dropwise. When the reaction was completed, extraction was performed with water and ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, treated with activated carbon, and filtered through Celite. The obtained filtrate was concentrated under reduced pressure and the obtained solid was suspended in n-hexane, filtered, and washed with n-hexane to obtain a white solid compound a-1 (1.51 kg, yield: 66%).

compound preparation of a-2

In a 2000 mL 3-neck round bottom flask, compound a-1 (1.5 kg, 0.586 mol), 1-bromo-2-nitrobenzene (260.5 g, 1.28 mol), tetrakis (triphenylphosphine) palladium (0) ( Pd(PPh ₃ ) ₄ , 27.11 g, 0.023 mol) was added, dioxane (1500 mL) and 2M sodium hydrogen carbonate were added, followed by heating to reflux for 12 hours. After completion of the reaction, the obtained solid was sufficiently washed with ethyl acetate and hexane and filtered under reduced pressure to obtain a pale yellow solid compound a-2 (1.01 kg, yield: 42%).

¹ H NMR (DMSO) δ[ppm]: 8.26 (m, 2H), 8.26 (d, 2H), 7.88 (t, 2H), 7.73-7.66 (m, 4H), 7.55 (m, 4H).

Preparation of compound a-3

Compound a-2 (1.0 kg, 0.244 mol) and triphenylphosphine (PPh ₃ , 191.7 g, 0.731 mol) were added to a 2000 mL 3-neck round bottom flask, and o-dichlorobenzene (1000 mL) was added. It was heated to reflux for an hour. After completion of the reaction, the obtained solid was sufficiently washed with methylene chloride and filtered under reduced pressure to obtain a pale yellow solid compound a-3 (42.2 g, yield: 50%).

¹ H NMR (DMSO) δ[ppm]: 11.69 (s, 2H), 8.60 (d, 2H), 8.14 (d, 2H), 7.64 (d, 2H), 7.54 (d, 2H), 7.50 (t, 2H), 7.42 (t, 2H).

Preparation of compound A

In a 2000 mL 3-neck round bottom flask, compound a-3 (50 g, 0.144 mol), 9-(3-bromophenyl)-9H-carbazole (23.2 g, 0.072 mol), sodium t-butoxide (20.8 g, 0.217 mol), tris(dibenzylideneacetone)dipalladium(0) (Pd ₂ (dba _{) 3} , 3.3 g, 0.0036 mol), and tri t-butylphosphine (P(t-Bu) ₃ , 2.92 g, 0.014 mol) was added, and the reactor was vacuumed again, followed by nitrogen filling. After adding nitrogen-filled toluene (1000 mL) to dissolve the reaction, the mixture was heated and stirred at 130° C. for 6 hours. After completion of the reaction, the reaction product was cooled to room temperature. Extracted with water and ethyl acetate, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was separated by a silica gel column (hexane: methylene chloride = 10: 1 (v: v)) to obtain a white solid compound A (27 g, yield: 32%).

¹ H NMR (CDCl ₃ ) δ[ppm]: 9.03 (s, 1H), 8.46 (m, 1H), 8.14 (m, 2H), 8.01 (d, 1H), 7.88 (d, 1H), 7.81 (d , 1H), 7.75 (d, 1H), 7.60 (m, 3H), 7.53 (m, 3H), 7.40 (m, 1H), 7.33 (m, 8H), 7.22 (m, 2H).

[Example 1] Preparation of Compound 1

Preparation of compound B-1

In a 3000mL 3-neck round bottom flask from which moisture was removed, 1-(3-hydroxypropyl)uracil (1-(3-Hydroxypropyl)uracil) (50 g, 0.293 mol), potassium phosphate (KH ₂ PO ₄ , 79.9 g, 0.588 mol) was added and the reactor was evacuated again, followed by nitrogen filling. Nitrogen-filled dimethyl sulfoxide (2000 mL) was added to dissolve the reaction, and then 1,3-dibromobenzene (69.3 g, 0.293 mol) was added and stirred at room temperature for 72 hours. After completion of the reaction, extraction was performed with water and methylene chloride, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was separated by a silica gel column (hexane: methylene chloride = 50: 1 (v: v)) to obtain a white solid compound B-1 (22 g, yield: 24%).

¹ H NMR (CDCl ₃ ) δ[ppm]: 9.75 (s, 1H), 7.42 (m, 2H), 7.27 (t, 1H), 7.13 (t, 1H), 6.95 (d, 1H), 5.63 (d , 1H), 4.09 (t, 2H), 3.96 (t, 2H), 1.99 (m, 2H).

Preparation of compound 2

In a 3000 mL 3-neck round bottom flask, compound A (10 g, 0.017 mol), compound B-1 (6.6 g, 0.02 mol), copper iodide (CuI, 3.2 g, 0.017 mol), potassium phosphate (5.3 g, 0.039) mol), and cyclohexanediamine (1.9 g, 0.017 mol) were added, and dioxane (1000 mL) was added to dissolve the reaction product, followed by heating and stirring at 50° C. for 50 hours. After completion of the reaction, the reaction product was cooled to room temperature, extracted with water and methylene chloride, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was separated with a silica gel column (hexane: methylene chloride = 10: 1 (v: v)) to obtain a solid, and the obtained solid was recrystallized from toluene and hexane to obtain a white solid compound 2 (7.6 g, yield) : 54%).

¹ H NMR (CDCl ₃ ) δ[ppm]: 9.60 (s, 1H), 8.15 (d, 2H), 8.00 (m, 2H), 7.86 (m, 3H), 7.75 (d, 2H), 7.55 (m , 7H), 7.42(m, 1H), 7.33(m, 6H), 7.24(m, 4H), 6.93(d, 2H), 5.66(d, 1H), 4.12(t, 2H), 3.98(t, 2H), 2.02 (m, 2H); MALDI-TOF MS: m/z 831.91, cal. 831.12.

[Example 2] Preparation of compound 26

Preparation of compound B-2

1-(3-hydroxypropyl)uracil (43.3 g, 0.254 mol) and potassium phosphate (KH ₂ PO ₄ , 34.5 g, 0.254 mol) were added to a 3000 mL 3-neck round bottom flask from which moisture was removed, and the reactor was vacuumed again. Then it was charged with nitrogen. Nitrogen-filled dimethyl sulfoxide (1500 mL) was added to dissolve the reaction, and then 1,3,5-tribromobenzene (40 g, 0.127 mol) was added and stirred at room temperature for 72 hours. After completion of the reaction, extraction was performed with water and methylene chloride, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was separated by a silica gel column (hexane: methylene chloride = 10: 1 (v: v)) to obtain a white solid compound B-2 (16 g, yield: 26%).

¹ H NMR (CDCl ₃ ) δ[ppm]: 9.75 (s, 2H), 7.58 (d, 2H), 6.79 (d, 2H), 6.30 (t, 1H), 5.67 (d, 2H), 4.09 (t , 4H), 3.98 (t, 4H), 2.02 (m, 4H).

Preparation compound 26

In a 3000 mL 3-neck round bottom flask, compound A (10 g, 0.017 mol), compound B-2 (10 g, 0.02 mol), copper iodide (CuI, 3.2 g, 0.017 mol), potassium phosphate (5.3 g, 0.039) mol), and cyclohexanediamine (1.9 g, 0.017 mol) were added, and dioxane (1000 mL) was added to dissolve the reaction product, followed by heating and stirring at 50° C. for 50 hours. After completion of the reaction, the reaction product was cooled to room temperature, extracted with water and methylene chloride, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was separated on a silica gel column (hexane: methylene chloride = 10: 1 (v: v)) to obtain a solid, and the obtained solid was recrystallized from toluene and hexane to obtain a white solid compound 26 (10 g, yield : 62%).

¹ H NMR (CDCl ₃ ) δ[ppm]: 9.60 (s, 2H), 8.16 (d, 2H), 8.14 (m, 2H), 8.02 (d, 2H), 7.85 (d, 1H), 7.76 (d , 1H), 7.56(m, 8H), 7.31(m, 7H), 7.22(m, 3H), 6.70(d, 2H), 6.22(t, 1H), 5.67(d, 2H), 4.01(m, 8H), 2.03 (m, 4H); MALDI-TOF MS: m/z 1000.06, cal. 999.31.

[Example 3] Fabrication of an organic light-emitting device using Compound 2 according to the present invention

A glass substrate with a size of 25 mm × 25 mm × 0.7 mm, having an ITO (indium tin oxide) transparent electrode line with a thin film thickness of 150 nm, was cleaned with ultrasonic waves in distilled water in which a detergent was dissolved for 20 minutes, and isopropyl alcohol was removed. Washed once for 10 minutes. After cleaning with isopropyl alcohol, the substrate was ultrasonically washed twice for 10 minutes each again using distilled water and dried. Then, oxygen/nitrogen plasma was treated for 2 minutes in a vacuum deposition equipment.

After the plasma work of the substrate is finished, the substrate is vacuum-adsorbed to the spin coater to manufacture the device for solution processing, and then PEDOT:PSS, a polythiophene derivative, a conductive polymer, to cover the transparent electrode on the surface where the transparent electrode line is formed ( After diluting poly(3,4-ethylenedioxythiophene)-poly(styrenesulfonate)) with isopropyl alcohol, spin-coating at 2000 rpm for 1 minute, drying it on a hot plate at 130°C for 30 minutes to form a 50 nm thin film. Used as an injection layer. Next, PVK (poly-N-vinylcarbazole) was diluted in toluene on the hole injection layer and spin-coated at 2000 rpm for 30 seconds to form a 15 nm hole transport layer after baking for 30 minutes on a hot plate at 130°C. Next, a solution (D) in which 0.5 wt% of AYPD, an iridium-based complex as a dopant, was dissolved in chlorobenzene, and a solution in which 1 wt% of the organic light-emitting compound 2 (Example 1) according to the present invention as a host was dissolved in toluene (H) was mixed at a volume ratio of 5:95 (D:H), spin-coated on the hole transport layer at 2000rpm for 30 seconds, and then baked on a hot plate at 80°C for 30 minutes to form a light emitting layer having a thickness of 30 nm. .

Then, TSPO1 (diphenyl-4-triphenylsilylphenylphosphine oxide) and TPBI (1,3,5-tris(N-phenylbenzimidazol-2-yl)benzene) were formed on the emission layer with an electron transport layer having a thickness of 25 nm, and then Liq (lithium quinolate) was deposited to form an electron injection layer having a thickness of 1 nm. Metal aluminum was deposited on the Liq film to form a metal cathode to fabricate an organic light-emitting device.

A light emission test was performed by applying a voltage of 0 to 15V to the organic light emitting device fabricated as described above, and the electroluminescence characteristics and basic physical properties measurement results are shown in Table 1 below.

[Example 4] Fabrication of an organic light-emitting device using Compound 26 according to the present invention

An organic light-emitting device was manufactured under the same process as in Example 3, except that Compound 26 was used instead of Compound 2 as the host material in Example 1, and the electroluminescence characteristics and basic physical properties measurement results are shown in Table 1 below. .

Efficiency (cd/A) Power efficiency (lm/W) Quantum efficiency (%) Color coordinates (x, y) Example 3 53.93 24.91 15.74 (0.304, 0.626) Example 4 55.02 26.18 16.06 (0.303, 0.625)

As shown in Table 1, it was confirmed that the organic light emitting device including the compound according to the present invention as a host material for light emission in the light emitting layer has excellent light emission characteristics in terms of efficiency, power efficiency, and quantum efficiency.

That is, when the compound having the characteristic structure according to the present invention is used as a host material for light emission in the light emitting layer, the density of holes and electrons is balanced to maximize the formation of excitons, thereby further lowering the driving voltage and By effectively confining excitons, efficiency, power efficiency, and quantum efficiency can be dramatically increased, and a roll-off phenomenon can be suppressed at a high current density to realize more excellent durability, thereby having a long lifespan.

Although the embodiments of the present invention have been described in detail as described above, those of ordinary skill in the art to which the present invention pertains, without departing from the spirit and scope of the present invention as defined in the appended claims. The invention may be implemented by various modifications. Therefore, changes to the embodiments of the present invention will not be able to depart from the technology of the present invention.

Claims (7)

An organic light-emitting compound represented by the following formula (1).
[Formula 1]

In Formula 1,
L ₁ is C1-C30 alkylene;
X ₁ is NR', O or S;
R'is hydrogen, deuterium, halogen, C1-C30 alkyl, C3-C30 cycloalkyl, C6-C30 aryl or C3-C30 heteroaryl;
m is an integer from 1 to 3;
Q is NR ₁ , O, S or CR ₂ R ₃ ;
R ₁ to R ₃ are each independently hydrogen, deuterium, halogen, C1-C30 alkyl, C3-C30 cycloalkyl, C6-C30 aryl or C3-C30 heteroaryl;
L ₂ and L ₃ are each independently C6-C30 arylene or C3-C30 heteroarylene;
Ar ₁ is C6-C30 aryl or C3-C30 heteroaryl;
The aryl or heteroaryl of Ar ₁ is C1-C30 alkyl, halo C1-C30 alkyl, halogen, cyano, C3-C30 cycloalkyl, C3-C30 heterocycloalkyl, C1-C30 alkoxy, C6-C30 aryloxy, C6 -C30 aryl C1-C30 alkyl, C6-C30 aryl, C3-C30 heteroaryl, mono or diC1-C30 alkylamino, mono or diC6-C30 arylamino, triC1-C30 alkylsilyl, diC1-C30 alkyl C6 -C30 arylsilyl, triC6-C30 arylsilyl, may be further substituted with one or more selected from the group consisting of nitro and hydroxy;
The heteroaryl and heteroarylene include one or more heteroatoms selected from B, N, O, S, P(=O), Si and P. The method of claim 1,
The organic light-emitting compound is an organic light-emitting compound represented by the following formula (2).
[Formula 2]

In Chemical Formula 2,
L ₁ is C1-C20 alkylene;
X ₁ is O or S;
m is an integer from 1 to 3;
Q is O or S;
Ar ₁ is C6-C20 aryl or C3-C20 heteroaryl;
The aryl or heteroaryl of Ar ₁ is C1-C20 alkyl, halo C1-C20 alkyl, halogen, cyano, C3-C20 cycloalkyl, C6-C20 aryl C1-C20 alkyl, C6-C20 aryl and C3-C20 heteroaryl It may be further substituted with one or more selected from the group consisting of. The method of claim 1,
The organic light-emitting compound is an organic light-emitting compound represented by the following formula (3).
[Formula 3]

In Chemical Formula 3,
n is an integer from 1 to 10;
m is an integer of 1 or 2;
Ar ₁ is selected from the following structures;

Y is CR ^a R ^b , NR ^c , S or O;
R ^a , R ^b , R ^c , R ₁₁ to R ₁₅ , R ₁₇ and R ₁₈ are each independently C1-C10 alkyl, C6-C12 aryl or C3-C12 heteroaryl. The method of claim 1,
Any one selected from the following compounds, organic light-emitting compounds.

An organic light-emitting device comprising the organic light-emitting compound according to any one of claims 1 to 4. The method of claim 5,
The organic light-emitting device includes a first electrode; A second electrode; And one or more organic material layers interposed between the first electrode and the second electrode, wherein the organic material layer includes a light-emitting layer containing the organic light-emitting compound. The method of claim 6,
The organic light-emitting device, wherein the organic light-emitting compound is included as a host of the light-emitting layer.