KR20170070826A - Organic electroluminescent compound and organic electroluminescent device comprising the same - Google Patents

Abstract

The present invention relates to an organic electroluminescent compound and an organic electroluminescent device including the same. The organic electroluminescent compound according to the present invention can provide an organic electroluminescent device having a low driving voltage and / or low power efficiency and / or a high luminous efficiency.

Description

TECHNICAL FIELD [0001] The present invention relates to an organic electroluminescent compound and an organic electroluminescent device including the same. BACKGROUND ART < RTI ID = 0.0 >

The present invention relates to an organic electroluminescent compound and an organic electroluminescent device including the same.

Among display devices, an electroluminescent device (EL device) is a self-luminous display device having a wide viewing angle, excellent contrast, and fast response speed. In 1987, Eastman Kodak Company developed an organic EL device using an aromatic diamine and an aluminum complex having low molecular weight as a light emitting layer forming material [Appl. Phys. Lett. 51, 913, 1987].

The most important factor determining the luminous efficiency in an organic electroluminescent device is a light emitting material. Fluorescent materials have been widely used as luminescent materials to date, but the development of phosphorescent materials has been widely studied in that phosphorescent materials can improve luminous efficiency up to 4 times the theoretical efficiency of phosphorescent materials in terms of the mechanism of electroluminescence . Until now, an iridium (III) complex series has been widely known as a phosphorescent material. Each RGB has bis (2- (2'-benzothienyl) -pyridinate-N, C-3 ') iridium (acetylacetonate ) [(acac) Ir (btp ) 2], tris (2-phenylpyridine) iridium [Ir (ppy) _3], bis (4,6-difluorophenyl pyridinyl Nei Sat -N, C2) avoid collision Ney And materials such as tolidium (Firpic) are known.

In the prior art, 4,4'-N, N'-dicarbazole-biphenyl (CBP) is the most widely known phosphorescent host material. In recent years, Pioneer and the like of Japan have been using (Bococuproine, BCP), aluminum (III) bis (2-methyl-8-quinolinate) (4-phenyl phenolate) Balq) as a host material and developed a high-performance organic electroluminescent device.

However, existing materials have advantages in terms of luminescence properties, but they have the following disadvantages: (1) They have a low glass transition temperature and a low thermal stability, which deteriorate during a high-temperature deposition process under vacuum, and the lifetime of the device deteriorates. (2) In the organic electroluminescent device, the power efficiency is in the relation of [(? / Voltage) x current efficiency], so that the power efficiency is inversely proportional to the voltage. In the organic electroluminescent device using the phosphorescent host material, The current efficiency (cd / A) is higher than that of the light emitting device, but the driving voltage is also very high, so there is no great advantage in terms of power efficiency (lm / w). (3) In addition, when used in an organic electroluminescent device, it is unsatisfactory in terms of operating life, and luminous efficiency is still required to be improved. Therefore, in order to realize excellent characteristics of the organic EL device, the materials constituting the organic material layer in the device, particularly the host or dopant constituting the light emitting material, must be appropriately selected.

Korean Patent Registration No. 10-1511115 discloses a compound having a structure in which two carbazoles are fused and an organic light emitting device including the same. However, the above literature discloses that two carbazoles are linked by the nitrogen atom contained in each carbazole as an aryl or heteroaryl linker, and one aryl contained in each carbazole is connected to each other to form a 7 to 10 member A compound having a structure in which a ring is formed and at the same time one aryl contained in each carbazole is bonded to each other with a heteroatom as a linker is not specifically disclosed.

Korean Registered Patent No. 10-1511115 (issued Apr. 6, 2015)

An object of the present invention is to provide an organic electroluminescent compound capable of firstly producing an organic electroluminescent device having a low driving voltage and / or low power efficiency and / or a high luminous efficiency, and secondly, the organic electroluminescent compound And an organic electroluminescent device.

As a result of intensive studies to solve the above technical problems, the present inventors have found that the organic electroluminescent compound having the specific structure described in the present invention can remarkably improve the power efficiency and / or luminous efficiency of the organic electroluminescent device, . More specifically, the present inventors have found that an organic electroluminescent compound represented by the following formula (1) achieves the above-mentioned object.

[Chemical Formula 1]

In Formula 1,

Ring Y is substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (3-30 membered) heteroaryl;

X is O, S or NR < _{5 &} gt ;;

R ₁ to R ₄ are each independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C 1 -C 30) alkyl, substituted or unsubstituted (C 6 -C 30) (C1-C30) alkylsilyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi (C6-C30) arylsilyl, substituted or unsubstituted tri Substituted or unsubstituted mono- or di- (C1-C30) alkylamino, substituted or unsubstituted mono- or di- (C6-C30) arylamino, C30) arylamino, or a substituted or unsubstituted (C3-C30) monocyclic or polycyclic alicyclic group, aromatic group, or a combination thereof, which is connected to an adjacent substituent, Hyangjok or carbon atoms of the ring of a combination thereof is optionally replaced by one or more hetero atoms selected from nitrogen, oxygen and sulfur;

R ₅ is selected from the group consisting of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C 1 -C 30) alkyl, substituted or unsubstituted (C 6 -C 30) aryl, substituted or unsubstituted (3-30 membered) (C1-C30) alkoxy, substituted or unsubstituted tri (C1-C30) alkylsilyl, substituted or unsubstituted di (C1-C30) (C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi (C6-C30) arylsilyl, substituted or unsubstituted tri (C6-C30) arylsilyl, substituted or unsubstituted mono- Or di- (C1-C30) alkylamino, substituted or unsubstituted mono- or di- (C6-C30) arylamino, or substituted or unsubstituted (C1-C30) alkyl (C6-C30) arylamino;

Wherein said heteroaryl comprises one or more heteroatoms selected from B, N, O, S, Si and P;

a and b are each independently an integer of 1 to 4, c and d are each independently an integer of 1 or 2, and when a to d are each an integer of 2 or more, each of R ₁ to R ₄ is the same or different .

The organic electroluminescent compound according to the present invention can produce an organic electroluminescent device having a low driving voltage and / or low power efficiency and / or a high luminous efficiency.

The present invention will now be described in more detail, but this should not be construed as limiting the scope of the present invention.

As used herein, the term " organic electroluminescent compound "means a compound that can be used in an organic electroluminescent device, and may be included in an arbitrary layer constituting an organic electroluminescent device, if necessary.

As used herein, the term " organic electroluminescent material " means a material that can be used in the organic electroluminescent device, and may include at least one compound, and may be included in any layer constituting the organic electroluminescent device, if necessary. For example, the organic electroluminescent material may be a hole injecting material, a hole transporting material, a hole assisting material, a light emitting auxiliary material, an electron blocking material, a light emitting material, an electron buffer material, have.

The compound represented by the formula (1) will be described in more detail as follows.

In Formula 1, X is O, S or NR < _{5 &} gt ;.

In formula (1), ring Y is substituted or unsubstituted (C6-C30) aryl or substituted or unsubstituted (3-30 membered heteroaryl), preferably substituted or unsubstituted , Or substituted or unsubstituted (5-25 membered) heteroaryl, more preferably substituted or unsubstituted (C6-C18) aryl, or substituted or unsubstituted (5-18 membered heteroaryl). According to one aspect of the disclosure, ring Y is selected from substituted or unsubstituted benzene, substituted or unsubstituted pyridine, substituted or unsubstituted pyrimidine, substituted or unsubstituted pyrazine, substituted or unsubstituted thiophene, Unsubstituted furan, and the benzene, pyridine, pyrimidine, pyrazine, thiophene or furan may be an unsubstituted ring.

R ₁ to R ₄ are each independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C 1 -C 30) alkyl, substituted or unsubstituted (C 6 -C 30) Substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C3-C30) alkoxy, substituted or unsubstituted tri (C1- (C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi (C6-C30) arylsilyl, substituted or unsubstituted tri Substituted or unsubstituted mono- or di- (C1-C30) alkylamino, substituted or unsubstituted mono- or di- (C6-C30) arylamino, (C6-C30) arylamino, or may be connected to adjacent substituents to form a ring of a single or multiple substituted or unsubstituted alicyclic (C3-C30) alicyclic, aromatic, or combination thereof, Alicyclic, aromatic, or a carbon atom of the ring is formed of a combination thereof is optionally replaced by one or more hetero atoms selected from nitrogen, oxygen and sulfur; Are each independently hydrogen, substituted or unsubstituted (C6-C25) aryl, or substituted or unsubstituted (5-25) heteroaryl; More preferably, each independently is hydrogen or substituted or unsubstituted (5-18 membered) heteroaryl; For example, hydrogen, triazinyl substituted with one or two phenyl, or unsubstituted pyridyl.

Wherein R ₅ is selected from the group consisting of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C 1 -C 30) alkyl, substituted or unsubstituted (C 6 -C 30) aryl, substituted or unsubstituted Substituted or unsubstituted (C1-C30) alkylsilyl, substituted or unsubstituted di (C1-C30) alkoxy, (C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi (C6-C30) arylsilyl, substituted or unsubstituted tri Substituted or unsubstituted mono- or di- (C 1 -C 30) alkylamino, substituted or unsubstituted mono- or di- (C 6 -C 30) arylamino, or substituted or unsubstituted (C 1 -C 30) ) Arylamino; Preferably a substituted or unsubstituted (C6-C25) aryl, or a substituted or unsubstituted (5-25 membered) heteroaryl; More preferably substituted or unsubstituted (C6-C18) aryl, or substituted or unsubstituted (5-18 membered heteroaryl); For example, substituted or unsubstituted phenyl, unsubstituted naphthylphenyl, unsubstituted biphenyl, unsubstituted terphenyl, triazinyl substituted with one or two phenyl, quinazolinyl substituted with phenyl, phenyl Quinoxalinyl substituted with one or two phenyl, or substituted pyridyl. Wherein the substituent of the substituted phenyl may be triazinyl substituted with one or two phenyl, triazinyl substituted with phenyl and / or biphenyl, quinoxalinyl substituted with phenyl, or unsubstituted pyridyl, The substituent of the substituted pyridyl may be triazinyl substituted with one or two phenyl.

Wherein heteroaryl comprises at least one heteroatom selected from B, N, O, S, Si and P, preferably comprising at least one heteroatom selected from N, O and S, Is a nitrogen-containing heteroaryl containing at least one N atom.

Wherein a and b are each independently an integer of 1 to 4, c and d are each independently an integer of 1 or 2, and when a to d are each an integer of 2 or more, each of R ₁ to R ₄ May be the same or different. Preferably, a to d are each independently an integer of 1.

According to one aspect of the present invention, in the above formula (1), ring Y is substituted or unsubstituted (C6-C25) aryl or substituted or unsubstituted (5-25) heteroaryl; X is O, S or NR < _{5 &} gt ;; R ₁ to R ₄ are each independently hydrogen, substituted or unsubstituted (C 6 -C 25) aryl, or substituted or unsubstituted (5-25 membered) heteroaryl; R < ₅ > is substituted or unsubstituted (C6-C25) aryl, or substituted or unsubstituted (5-25 membered) heteroaryl; a to d each independently represent an integer of 1;

According to one aspect of the present invention, in the above formula (1), ring Y is substituted or unsubstituted (C6-C18) aryl or substituted or unsubstituted (5-18 membered heteroaryl; X is O, S or NR < _{5 &} gt ;; R ₁ to R ₄ are each independently hydrogen or substituted or unsubstituted (5-18 membered) heteroaryl; R ₅ is substituted or unsubstituted (C6-C18) aryl, or substituted or unsubstituted (5-18 membered) heteroaryl; a to d each independently represent an integer of 1;

According to one aspect of the present invention, in the above Formula 1, the ring Y is a substituted or unsubstituted benzene, a substituted or unsubstituted pyridine, a substituted or unsubstituted pyrimidine, a substituted or unsubstituted pyrazine, a substituted or unsubstituted Thiophene, or substituted or unsubstituted furan; X is O, S or NR < _{5 &} gt ;; R ₁ to R ₄ are each independently hydrogen, trizinyl substituted by diphenyl, or unsubstituted pyridyl; R ₅ is selected from the group consisting of substituted or unsubstituted phenyl, unsubstituted naphthylphenyl, unsubstituted biphenyl, unsubstituted terphenyl, diphenyl substituted triazinyl, quinazolinyl substituted with phenyl, Pyrimidinyl substituted with salinyl, diphenyl, or substituted pyridyl; a to d each independently represent an integer of 1;

The term "(C 1 -C 30) alkyl" as used herein means straight-chain or branched alkyl having 1 to 30 carbon atoms constituting the chain, wherein the number of carbon atoms is preferably 1 to 20, more preferably 1 to 10 . Specific examples of the alkyl include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl and tert-butyl. The term "(C2-C30) alkenyl" as used herein means straight chain or branched alkenyl having 2 to 30 carbon atoms constituting the chain, preferably having 2 to 20 carbon atoms, more preferably 2 to 10 desirable. Specific examples of the alkenyl include vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 2-methylbut-2-enyl and the like. As used herein, the term "(C2-C30) alkynyl" means straight chain or branched chain alkynyl having 2 to 30 carbon atoms constituting the chain, preferably having 2 to 20 carbon atoms, more preferably 2 to 10 desirable. Examples of the alkynyl include ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl and 1-methylpent-2-onyl. The term "(C3-C30) cycloalkyl" as used herein means a single ring or multiple ring hydrocarbon having 3 to 30 ring skeletal carbon atoms, preferably 3 to 20 carbon atoms, and more preferably 3 to 7 carbon atoms. Examples of the cycloalkyl include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and the like. Refers to a group consisting of B, N, O, S, Si and P, preferably O (O) , S and N, and includes, for example, tetrahydrofuran, pyrrolidine, thiolane, tetrahydropyran and the like. The term "(C6-C30) aryl" as used herein means a single ring or fused ring radical derived from an aromatic hydrocarbon having 6 to 30 ring skeletal carbon atoms, preferably 6 to 20 carbon atoms, more preferably 6 Lt; / RTI > The aryl may be partially saturated, including those having a spiro structure. Examples of the aryl include phenyl, biphenyl, terphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl, benzofluorenyl, dibenzofluorenyl, Naphthyl, naphthyl, phenyl, phenanthrenyl, anthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, crycenyl, naphthacenyl, fluoranthenyl, spirobifluorenyl and the like. As used herein, "(3-30) heteroaryl" means an aryl group having at least one heteroatom selected from the group consisting of B, N, O, S, Si and P having 3 to 30 ring skeletal atoms. The number of heteroatoms is preferably 1 to 4, and may be a monocyclic ring system or a fused ring system condensed with at least one benzene ring, and may be partially saturated. In addition, the heteroaryl in the present application includes a heteroaryl group having one or more heteroaryl or aryl groups connected to a heteroaryl group by a single bond, and having a spiro structure. Examples of such heteroaryls include furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl , Monocyclic heteroaryl such as triazolyl, tetrazolyl, furanzyl, pyridyl, pyrazinyl, pyrimidinyl and pyridazinyl, benzofuranyl, benzothiophenyl, isobenzofuranyl, dibenzofuranyl, di Benzoimidazolyl, benzothiazolyl, benzothiazolyl, benzoisothiazolyl, benzooxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, Fused ring heteroaryl such as furanyl, quinazolinyl, quinazolinyl, quinazolinyl, carbazolyl, benzocarbazolyl, phenoxaphyl, phenothiazinyl, phenanthridinyl, benzodioxolyl, dihydroacrylidinyl and the like. As used herein, "halogen" includes F, Cl, Br, and I atoms.

Also, in the phrase "substituted or unsubstituted" described herein, "substituted" means that a hydrogen atom is replaced with another atom or another functional group (ie, a substituent) in a certain functional group. In the rings Y and R ₁ to R ₅ of formula I, substituted alkyl, substituted aryl, substituted heteroaryl, substituted cycloalkyl, substituted alkoxy, substituted trialkylsilyl, substituted dialkylarylsilyl, substituted Substituted mono-or di-alkylamino, substituted mono-or di-arylamino, substituted alkylarylamino, and substituted monocyclic or polycyclic alicyclic, aromatic, Or a combination thereof, each independently selected from the group consisting of deuterium; halogen; Cyano; Carboxyl; Nitro; Hydroxy; (C1-C30) alkyl; Halo (C1-C30) alkyl; (C2-C30) alkenyl; (C2-C30) alkynyl; (C1-C30) alkoxy; (C1-C30) alkylthio; (C3-C30) cycloalkyl; (C3-C30) cycloalkenyl; (3-7 membered) heterocycloalkyl; (C6-C30) aryloxy; (C6-C30) arylthio; (3-30 membered) heteroaryl which is unsubstituted or substituted by (C1-C30) alkyl and / or (C6-C30) aryl; (C6-C30) aryl unsubstituted or substituted with (3-30) heteroaryl; Tri (C1-C30) alkylsilyl; Tri (C6-C30) arylsilyl; Di (C1-C30) alkyl (C6-C30) arylsilyl; (C1-C30) alkyldi (C6-C30) arylsilyl; Amino; Mono-or di- (C1-C30) alkylamino; Mono-or di- (C6-C30) arylamino; (C1-C30) alkyl (C6-C30) arylamino; (C1-C30) alkylcarbonyl; (C1-C30) alkoxycarbonyl; (C6-C30) arylcarbonyl; Di (C6-C30) arylboronyl; Di (C1-C30) alkylboronyl; (C1-C30) alkyl (C6-C30) arylboronyl; (C6-C30) aryl (C1-C30) alkyl; And (C6-C30) aryl optionally substituted with (5-18) membered heteroaryl, each of which is optionally substituted with one or more substituents selected from the group consisting of (C1-C30) alkyl , And (5-25) heteroaryl substituted or unsubstituted with (C6-C25) aryl, more preferably each independently is unsubstituted (C6-C18) aryl, and (5-18 member) heteroaryl, unsubstituted or substituted with (C6-C18) aryl, and examples thereof include unsubstituted phenyl, unsubstituted naphthyl, unsubstituted biphenyl, Unsubstituted pyridyl, triazinyl substituted with one or two phenyl, triazinyl substituted with phenyl and / or biphenyl, and quinoxalinyl substituted with phenyl.

The organic electroluminescent compound of Formula 1 may be more specifically exemplified by the following compounds, but is not limited thereto.

The organic electroluminescent compound according to the present invention can be produced by a synthesis method known to a person skilled in the art by reference to the following Reaction Scheme 1, but is not limited thereto.

[Reaction Scheme 1]

In the above Reaction Scheme 1, the ring Y, R ₁ to R ₄ , a to d are the same as defined in the formula (1).

In addition, the present invention can provide an organic electroluminescent material including the organic electroluminescent compound of Formula 1, and an organic electroluminescent device including the above material.

The material may be made of the organic electroluminescent compound of the present invention alone, and may further include common materials included in the organic electroluminescent material.

An organic electroluminescent device according to the present invention includes a first electrode; A second electrode; And at least one organic material layer interposed between the first electrode and the second electrode, and the organic material layer may include at least one organic electroluminescent compound represented by Formula 1.

One of the first electrode and the second electrode may be an anode, and the other may be a cathode. The organic material layer includes a light emitting layer, and the hole transporting layer, the hole transporting layer, the hole transporting layer, the light emission assisting layer, the electron transporting layer, the electron injecting layer, the interlayer, the hole blocking layer, And may further include at least one layer selected.

The light-emission-assisting layer may be disposed between the anode and the light-emitting layer or between the cathode and the light-emitting layer. When the light-emission-assisting layer is positioned between the anode and the light-emitting layer, the injection and / And can be used for blocking the overflow. When the luminescent auxiliary layer is located between the cathode and the luminescent layer, the luminescent auxiliary layer can be used for smoothly injecting and / or transporting electrons or blocking overflow of holes. Further, the hole-assist layer is located between the hole-transporting layer (or the hole-injecting layer) and the light-emitting layer and can exhibit an effect of smoothly blocking or blocking the hole transfer rate (or injection rate) Can be adjusted. Further, the electron blocking layer is located between the hole transporting layer (or hole injection layer) and the light emitting layer, and can block the electron overflow from the light emitting layer to confine the exciton in the light emitting layer to prevent light leakage. When the organic electroluminescent device includes two or more hole transporting layers, the hole transporting layer, which is further included, may be used as a hole-transporting layer or an electron blocking layer. The light-emitting auxiliary layer, the hole assist layer, or the electron blocking layer may have an effect of improving the efficiency and / or lifetime of the organic electroluminescent device.

The organic electroluminescent compound of Formula 1 may be included in the light emitting layer. When used in the light emitting layer, the organic electroluminescent compound of Formula 1 of the present invention may be included as a host material. Preferably, the light emitting layer may further include at least one dopant. If necessary, a compound other than the organic electroluminescent compound of Formula 1 may further be included as a second host material. Here, the weight ratio of the first host material to the second host material ranges from 1:99 to 99: 1.

The second host material may be any known phosphorescent host, but is preferably selected from the group consisting of compounds represented by the following general formulas (11) to (16) in view of luminous efficiency.

(11)

[Chemical Formula 12]

[Chemical Formula 13]

[Chemical Formula 14]

[Chemical Formula 15]

In the above Formulas 11 to 15,

Cz has the following structure,

A is -O- or -S-;

R ₂₁ to R ₂₄ each independently represent hydrogen, deuterium, halogen, substituted or unsubstituted (C 1 -C 30) alkyl, substituted or unsubstituted (C 6 -C 30) aryl, substituted or unsubstituted heteroaryl and aryl, or _{-SiR 25 R 26 R 27, R} 25 to R ₂₇ each independently represent a substituted or unsubstituted (C1-C30) alkyl, or substituted or unsubstituted (C6-C30) aryl; L ₄ is a single bond, substituted or unsubstituted (C 6 -C 30) arylene, or substituted or unsubstituted (5-30 membered) heteroarylene; M is a substituted or unsubstituted (C6-C30) aryl, or a substituted or unsubstituted (5-30 membered) heteroaryl; Y ₁ and Y ₂ are each independently -O-, -S-, -NR ₃₁ -, or -CR ₃₂ R ₃₃ - and Y ₁ and Y ₂ are not simultaneously present; R ₃₁ to R ₃₃ are each independently a substituted or unsubstituted (C 1 -C 30) alkyl, a substituted or unsubstituted (C 6 -C 30) aryl, or a substituted or unsubstituted (5-30 membered) ₃₂ and R ₃₃ may be the same or different; j, k, l and m are each independently an integer of 0 to 4, q is an integer of 0 to 3, and h, i, j, k and l are each independently an integer of 1 to 3, , each of (Cz-L ₄ ), (Cz), each R ₂₁ , each R ₂₂ , each R _23, or each R ₂₄ may be the same or different when m or q is an integer of 2 or more .

[Chemical Formula 16]

In Formula 16,

Y ₃ to Y ₅ are each independently CR ₃₄ or N, and R ₃₄ Is hydrogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (5-30 membered) heteroaryl;

B ₁ and B ₂ are each independently hydrogen, substituted or unsubstituted (C 6 -C 30) aryl, or substituted or unsubstituted (5-30 membered) heteroaryl;

B ₃ is substituted or unsubstituted (C 6 -C 30) aryl, or substituted or unsubstituted (5-30 membered) heteroaryl;

L ₅ is a single bond, substituted or unsubstituted (C6-C30) arylene, or substituted or unsubstituted (5-30 membered heteroarylene).

Specifically, preferred examples of the second host material are as follows.

 [Wherein TPS is a triphenylsilyl group]

The dopant included in the organic electroluminescent device of the present application is preferably at least one phosphorescent dopant. The phosphorescent dopant material to be applied to the organic electroluminescent device of the present invention is not particularly limited, but a complex compound of a metal atom selected from iridium (Ir), osmium (Os), copper (Cu) and platinum (Pt) And more preferably an ortho-metallated complex compound of a metal atom selected from iridium (Ir), osmium (Os), copper (Cu) and platinum (Pt), and still more preferably an orthometallated iridium complex compound.

As the dopant contained in the organic electroluminescent device of the present invention, compounds represented by the following formulas (101) to (103) may be used.

(101)      (103)

In the above formulas (101) to (103)

L is selected from the following structures;

R ₁₀₀ is hydrogen, deuterium, substituted or unsubstituted (C 1 -C 30) alkyl, or substituted or unsubstituted (C 3 -C 30) cycloalkyl;

R ₁₀₁ to R ₁₀₉ and R ₁₁₁ to R ₁₂₃ are each independently selected from the group consisting of hydrogen, deuterium, halogen, (C 1 -C 30) alkyl substituted or unsubstituted with halogen, substituted or unsubstituted (C 3 -C 30) Unsubstituted (C6-C30) aryl, cyano, or substituted or unsubstituted (C1-C30) alkoxy; R ₁₀₆ to R ₁₀₉ may form a fused ring in which adjacent substituents are connected to each other to form a substituted or unsubstituted fused ring, for example, fluorene substituted or unsubstituted with alkyl, dibenzothiophene substituted or unsubstituted with alkyl, Or dibenzofuran which is substituted or unsubstituted with alkyl is possible; R ₁₂₀ to R ₁₂₃ may form a fused ring in which adjacent substituents are connected to each other to form a substituted or unsubstituted fused ring, for example, quinoline substituted or unsubstituted with alkyl or aryl;

R ₁₂₄ to R ₁₂₇ are each independently hydrogen, deuterium, halogen, substituted or unsubstituted (C 1 -C 30) alkyl, or substituted or unsubstituted (C 6 -C 30) aryl; R ₁₂₄ to R ₁₂₇ may form a fused ring in which adjacent substituents are connected to each other to form a substituted or unsubstituted fused ring, for example, fluorene substituted or unsubstituted with alkyl, dibenzothiophene substituted or unsubstituted with alkyl, Or dibenzofuran which is substituted or unsubstituted with alkyl is possible;

R ₂₀₁ to R ₂₁₁ each independently represents hydrogen, deuterium, halogen, (C 1 -C 30) alkyl substituted or unsubstituted with halogen, substituted or unsubstituted (C 3 -C 30) cycloalkyl, or substituted or unsubstituted -30) aryl, and R < ₂₀₈ &_gt; to R < ₂₁₁ &_gt; may form a fused ring in which adjacent substituents are connected to each other to form a substituted or unsubstituted fused ring. For example, fluorine, substituted or unsubstituted alkyl, Dibenzothiophene, or dibenzofuran substituted or unsubstituted with alkyl is possible;

f and g are each independently an integer of 1 to 3; When f or g is an integer of 2 or more, each R ₁₀₀ may be the same or different from each other;

n is an integer of 1 to 3;

Specific examples of the dopant compound are as follows.

The present invention can provide a composition for manufacturing an organic electroluminescent device in a further aspect. The composition may include a compound of the present invention as a host material or a hole transporting layer material.

Further, the organic electroluminescent device of the present invention includes a first electrode; A second electrode; And at least one organic material layer interposed between the first electrode and the second electrode, wherein the organic material layer includes a light emitting layer, and the light emitting layer may include the composition for an organic electroluminescent device of the present invention.

The organic electroluminescent device of the present invention includes the organic electroluminescent compound of Formula 1, and at the same time, may include at least one compound selected from the group consisting of an arylamine-based compound and a styrylarylamine-based compound.

In addition, in the organic electroluminescent device of the present application, in addition to the organic electroluminescent compound of Formula 1, an organic electroluminescent compound of Group 1, 2, 4, 5 period transition metal, lanthanide series and d- And the organic material layer may further include a light emitting layer and a charge generating layer.

In addition, the organic electroluminescent device of the present invention may emit white light by further including at least one light emitting layer containing a blue, red or green light emitting compound known in the art, in addition to the compound of the present invention. Further, if necessary, it may further include a yellow or orange light emitting layer.

In the organic electroluminescent device of the present invention, one layer selected from a chalcogenide layer, a metal halide layer and a metal oxide layer (hereinafter referred to as " surface layer ") is formed on the inner surface of at least one of the pair of electrodes, Or more. Concretely, it is preferable to dispose a halogenated metal layer or a metal oxide layer on the surface of the anode on the side of the light emitting medium layer and on the surface of the cathode on the side of the light emitting medium layer, with a chalcogenide (including oxide) layer of a metal of silicon and aluminum Do. Thus, stabilization of the drive can be obtained. Preferable examples of the chalcogenide include SiO _x (1? _X ? 2), AlO _x (1? _X ? 1.5), SiON and SiAlON. Preferred examples of the halogenated metal include LiF, MgF ₂ , CaF ₂ , Rare-earth metals, etc. Preferred examples of the metal oxides include Cs ₂ O, Li ₂ O, MgO, SrO, BaO, CaO and the like.

Further, in the organic electroluminescent device of the present invention, a mixed region of the electron transfer compound and the reducing dopant, or a mixed region of the hole transport compound and the oxidative dopant, may be disposed on at least one surface of the pair of electrodes thus manufactured desirable. In this way, since the electron transfer compound is reduced to an anion, it becomes easy to inject and transfer electrons from the mixed region to the light emitting medium. Further, since the hole transport compound is oxidized and becomes a cation, it becomes easy to inject and transport holes from the mixed region into the light emitting medium. Preferred oxidizing dopants include various Lewis acids and acceptor compounds, and preferred reducing dopants include alkali metals, alkali metal compounds, alkaline earth metals, rare earth metals, and mixtures thereof. Also, a white organic electroluminescent device having two or more light emitting layers can be manufactured using a reducing dopant layer as a charge generating layer.

The formation of each layer of the organic electroluminescent device of the present invention may be performed by a dry film forming method such as vacuum deposition, sputtering, plasma or ion plating, or by a method such as ink jet printing, nozzle printing, slot coating, , Spin coating, dip coating, and flow coating may be used.

In the case of the wet film formation method, a thin film is formed by dissolving or dispersing a material forming each layer in an appropriate solvent such as ethanol, chloroform, tetrahydrofuran, dioxane, etc., And it may be any thing that does not have a problem in the tabernacle.

Hereinafter, the method for preparing an organic electroluminescent compound according to the present invention and physical properties thereof are described in order to understand the present invention in detail. However, the present invention is not limited to the following examples.

[ Example  1] Preparation of Compound C-1

1) Synthesis of Compound 1-1

The reaction vessel was charged with Compound A (39 g, 132 mmol), 1-bromo-2-nitrobenzene (24 g, 120 mmol), tetrakis (triphenylphosphine) palladium (7 g, 6.0 mmol) (41 g, 300 mmol), toluene (600 mL), and ethanol (140 mL) were added, and thereto was added 140 mL of distilled water, followed by stirring at 120 ° C for 5 hours. After completion of the reaction, toluene and ethanol were removed by a rotary evaporator, and the mixture was extracted with methylene chloride and distilled water. The organic layer was dried with magnesium sulfate. The solvent was removed using a rotary evaporator and then purified by column chromatography to obtain Compound 1-1 (34.4 g, yield: 91%).

2) Synthesis of Compound 1-2

Compound ( 1-1) (34.4 g, 119 mmol) and 500 mL of tetrahydrofuran were added to the reaction vessel and stirred at room temperature. N-bromosuccinimide (NBS) (23.3 g, 131 mmol) was dissolved in 300 mL of tetrahydrofuran Lt; / RTI > After stirring at room temperature for 6 hours, the reaction mixture was extracted with methylene chloride and distilled water, and the organic layer was dried with magnesium sulfate. The solvent was removed by a rotary evaporator and then purified by column chromatography to obtain Compound 1-2 (41 g, yield: 94%).

3) Synthesis of Compound 1-3

To the reaction vessel was added compound 1-2 (40 g, 109 mmol), bis (pinacolato) diboron (36 g, 142 mmol), dichloro (triphenylphosphine) palladium (3.8 g, 5.5 mmol), potassium acetate 27 g, 273 mmol) and 1,4-dioxane (700 mL), and the mixture was stirred at 160 ° C for 6 hours. After the reaction was completed, the mixture was cooled to room temperature, and the solid was removed through a Celite filter. The solvent was removed by a rotary evaporator, and the residue was purified by column chromatography to obtain Compound 1-3 (36 g, yield: 80%).

4) Synthesis of Compound 1-4

A reaction vessel Compound 1-3 (45 g, 109 mmol) , 1- bromo-2-nitro-benzene (26.4 g, 130.8 mmol), tetrakis (triphenylphosphine) palladium (5.5 g, 6.3 mmol), Sodium carbonate (18.3 g, 218 mmol) and tetrahydrofuran (1000 mL) were added, and 436 mL of distilled water was added thereto, followed by stirring at 100 ° C for 4 hours. After completion of the reaction, tetrahydrofuran was removed by a rotary evaporator, and the mixture was extracted with methylene chloride and distilled water. The organic layer was dried with magnesium sulfate. The solvent was removed by a rotary evaporator, and the residue was purified by column chromatography to obtain Compound 1-4 (34 g, yield: 76%).

5) Synthesis of Compound 1-5

To the reaction vessel was added compound 1-4 (10 g, 24.4 mmol), biphenyltriazine chloride (7.84 g, 29.3 mmol), potassium carbonate (10.1 g, 73.2 mmol) and 4- dimethylaminopyridine (2.98 g, 24.4 mmol) , And 244 mL of dimethylformamide were placed, and the mixture was stirred at 100 ° C for 5 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, and then 200 mL of methanol and 400 mL of distilled water were added to the reaction solution to terminate the reaction, and a solid compound was obtained through a filter. The obtained solid compound was dried and then purified by column chromatography to obtain Compound 1-5 (11 g, yield: 69%).

6) Synthesis of Compound 1-6

Compound 1-5 (9.5 g, 14.8 mmol), 70 mL of triethylphosphite and 100 mL of 1,2-dichlorobenzene were placed in a reaction vessel and stirred at 200 ° C for 5 hours. After the reaction was completed, the solvent was distilled off under reduced pressure, and the organic layer was washed with distilled water and extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, and the solvent was removed using a rotary evaporator. This was then recrystallized from ethyl acetate and methanol to obtain Compound 1-6 (5.2 g, yield: 61%).

7) Synthesis of Compound C-1

A reaction vessel Compound 1-6 (14 g, 24.3 mmol) , 1- bromo-2-iodo-benzene (7 g, 29.2 mmol), copper (1.54 g, 24.3 mmol), potassium carbonate (13.4g, 97.2 mmol ) And 300 mL of 1,2-dichlorobenzene were placed, and the mixture was stirred at 200 占 폚 for 8 hours. When the reaction was completed, the solvent was distilled off under reduced pressure, and the residue was purified by column chromatography. Thereafter, the compound C-1 (4.3 g, yield: 27%) was obtained by recrystallization from toluene.

Hereinafter, the luminescent characteristics of the organic electroluminescent device including the compound of the present invention will be described in order to understand the present invention in detail. However, the present invention is not limited to the following examples.

 [device Manufacturing example  RTI ID = 0.0 > 1-1] < / RTI > OLED  Device Manufacturing

OLED devices were prepared using the organic electroluminescent compound of the present invention. First, a transparent electrode ITO thin film (10? /?) On a glass substrate for OLED (manufactured by Geomatex) was subjected to ultrasonic cleaning using acetone, ethanol and distilled water sequentially, and then stored in isopropanol before use. Next, the ITO substrate was mounted on the substrate holder of the vacuum deposition apparatus, the compound HI-1 was placed in the cell in the vacuum deposition apparatus, the chamber was evacuated until the degree of vacuum reached 10 ^-6 torr, And evaporated to deposit a first hole injection layer having a thickness of 80 nm on the ITO substrate. Then, a compound HI-2 was added to another cell in a vacuum deposition apparatus, and a current was applied to the cell to evaporate the second hole injection layer to deposit a second hole injection layer having a thickness of 5 nm on the first hole injection layer. Compound HT-1 was then added to another cell in the vacuum evaporation apparatus, and a current was applied to the cell to evaporate the first hole transport layer to deposit a first hole transport layer having a thickness of 10 nm on the second hole injection layer. Compound HT-2 was then added to another cell in the vacuum vapor deposition apparatus and a second hole transporting layer having a thickness of 30 nm was deposited on the first hole transporting layer by applying current to the cell. A hole injecting layer and a hole transporting layer were formed, and then a light emitting layer was deposited thereon as follows. Compound C-1 as a host is placed in one cell in a vacuum deposition apparatus, Compound D-74 is added as a dopant in another cell, and at the same time, the dopant material is vaporized at different rates to obtain a total amount of host and dopant Was doped in an amount of 10 wt% to deposit a light emitting layer with a thickness of 40 nm on the second hole transporting layer. Then, to another cell in two places of the compound ET-1 and Compound EI -1 respectively 4: 6 was deposited by evaporation at a rate of the electron transport layer of 35 nm thickness on the light emitting layer. Subsequently, a compound EI- 1 was deposited on the electron transport layer to a thickness of 2 nm as an electron injection layer, and then an Al cathode was deposited on the electron injection layer to a thickness of 80 nm using another vacuum deposition apparatus to manufacture an OLED device Respectively. Each compound was purified by vacuum sublimation under 10 ^-6 torr.

[ Comparative Example  1-1] Using a conventional light emitting material as a host OLED  Device Manufacturing

OLED devices were manufactured in the same manner as in the Device Production Example 1-1, except that the following compound CBP was used as a host.

To the at least a 10 mA / cm ² based on the drive voltage of the organic EL device prepared as the luminous efficiency, power efficiency and CIE color coordinates are shown in Table 1 below.

[Table 1]

[device Manufacturing example  RTI ID = 0.0 > 2-1] < / RTI > OLED  Device Manufacturing

An OLED device was prepared in the same manner as in the Device Production Example 1-1 except that the compound D-1 was used as a dopant.

[ Comparative Example  2-1] Using a conventional light emitting material as a host OLED  Device Manufacturing

A luminescent layer of 40 nm in thickness was deposited on the second hole transport layer using the following compound CBP as the host material and compound D-1 as the dopant, and the following compound Balq was deposited as a hole blocking layer to a thickness of 10 nm after then, to another cell in two places of the compound ET-1 and compound EI -1 4: the same procedure it was the evaporated to 6 the speed of depositing the electron transport layer of 25 nm of thickness on the light-emitting layer other than the device produced in example 1-1 To prepare an OLED device.

The driving voltage, the luminous efficiency, the power efficiency, and the CIE color coordinates of the organic electroluminescent device manufactured as described above with reference to the luminance of 1,000 nits are shown in Table 2 below.

[Table 2]

The organic electroluminescent device comprising the organic electroluminescent compound of the present invention has lower driving voltage, higher power efficiency and luminescent efficiency than the organic electroluminescent device comprising the conventional organic electroluminescent compound And the like.

Claims (8)

An organic electroluminescent compound represented by the following formula (1).
[Chemical Formula 1]

In Formula 1,
Ring Y is substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (3-30 membered) heteroaryl;
X is O, S or NR < _{5 &} gt ;;
R ₁ to R ₄ are each independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C 1 -C 30) alkyl, substituted or unsubstituted (C 6 -C 30) (C1-C30) alkylsilyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi (C6-C30) arylsilyl, substituted or unsubstituted tri Substituted or unsubstituted mono- or di- (C1-C30) alkylamino, substituted or unsubstituted mono- or di- (C6-C30) arylamino, C30) arylamino, or a substituted or unsubstituted (C3-C30) monocyclic or polycyclic alicyclic group, aromatic group, or a combination thereof, which is connected to an adjacent substituent, Hyangjok, or a carbon atom of a ring of a combination thereof is optionally replaced by one or more hetero atoms selected from nitrogen, oxygen and sulfur;
R ₅ is selected from the group consisting of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C 1 -C 30) alkyl, substituted or unsubstituted (C 6 -C 30) aryl, substituted or unsubstituted (3-30 membered) (C1-C30) alkoxy, substituted or unsubstituted tri (C1-C30) alkylsilyl, substituted or unsubstituted di (C1-C30) (C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi (C6-C30) arylsilyl, substituted or unsubstituted tri (C6-C30) arylsilyl, substituted or unsubstituted mono- Or di- (C1-C30) alkylamino, substituted or unsubstituted mono- or di- (C6-C30) arylamino, or substituted or unsubstituted (C1-C30) alkyl (C6-C30) arylamino;
Wherein said heteroaryl comprises one or more heteroatoms selected from B, N, O, S, Si and P;
a and b are each independently an integer of 1 to 4, c and d are each independently an integer of 1 or 2, and when a to d are each an integer of 2 or more, each of R ₁ to R ₄ is the same or different . 3. The compound of claim 1, wherein Ring Y and R ₁ to R ₅ are alkyl substituted, substituted aryl, substituted heteroaryl, substituted cycloalkyl, substituted alkoxy, substituted trialkylsilyl, substituted dialkylarylsilyl, Substituted mono-or dialkylamino, substituted alkyldiarylsilyl, substituted triarylsilyl, substituted mono- or di-alkylamino, substituted mono- or di-arylamino, substituted alkylarylamino, and substituted mono- or poly- Aromatic, or combination thereof, is independently selected from the group consisting of deuterium; halogen; Cyano; Carboxyl; Nitro; Hydroxy; (C1-C30) alkyl; Halo (C1-C30) alkyl; (C2-C30) alkenyl; (C2-C30) alkynyl; (C1-C30) alkoxy; (C1-C30) alkylthio; (C3-C30) cycloalkyl; (C3-C30) cycloalkenyl; (3-7 membered) heterocycloalkyl; (C6-C30) aryloxy; (C6-C30) arylthio; (3-30 membered) heteroaryl which is unsubstituted or substituted by (C1-C30) alkyl or (C6-C30) aryl; (C6-C30) aryl unsubstituted or substituted with (3-30) heteroaryl; Tri (C1-C30) alkylsilyl; Tri (C6-C30) arylsilyl; Di (C1-C30) alkyl (C6-C30) arylsilyl; (C1-C30) alkyldi (C6-C30) arylsilyl; Amino; Mono-or di- (C1-C30) alkylamino; Mono-or di- (C6-C30) arylamino; (C1-C30) alkyl (C6-C30) arylamino; (C1-C30) alkylcarbonyl; (C1-C30) alkoxycarbonyl; (C6-C30) arylcarbonyl; Di (C6-C30) arylboronyl; Di (C1-C30) alkylboronyl; (C1-C30) alkyl (C6-C30) arylboronyl; (C6-C30) aryl (C1-C30) alkyl; And (C1-C30) alkyl (C6-C30) aryl. The method according to claim 1,
The ring Y is a substituted or unsubstituted benzene, a substituted or unsubstituted pyridine, a substituted or unsubstituted pyrimidine, an unsubstituted pyrazine, a substituted or unsubstituted thiophene, or a substituted or unsubstituted furan, compound. The method according to claim 1,
Ring Y is substituted or unsubstituted (C6-C25) aryl, or substituted or unsubstituted (5-25 membered) heteroaryl;
R ₁ to R ₄ are each independently hydrogen, substituted or unsubstituted (C 6 -C 25) aryl, or substituted or unsubstituted (5-25 membered) heteroaryl;
R < ₅ > is substituted or unsubstituted (C6-C25) aryl, or substituted or unsubstituted (5-25 membered) heteroaryl;
a to d each independently represent an integer of 1; The method according to claim 1,
Ring Y is substituted or unsubstituted (C6-C18) aryl, or substituted or unsubstituted (5-18 membered) heteroaryl;
R ₁ to R ₄ are each independently hydrogen or substituted or unsubstituted (5-18 membered) heteroaryl;
R ₅ is substituted or unsubstituted (C6-C18) aryl, or substituted or unsubstituted (5-18 membered) heteroaryl;
a to d each independently represent an integer of 1; The organic electroluminescent compound according to claim 1, wherein the compound represented by the formula (1) is selected from the following.

A host material comprising the organic electroluminescent compound according to claim 1. An organic electroluminescent device comprising the organic electroluminescent compound according to claim 1.