JP6525382B2 - Novel organic electroluminescent compound and organic electroluminescent device comprising the same - Google Patents

Description

  The present disclosure relates to novel organic electroluminescent compounds, and organic electroluminescent devices comprising the same.

  Electroluminescent (EL) devices are advantageous self-emitting devices in that they provide a wider viewing angle, better contrast ratio, and faster response time. Organic EL devices were first developed by Eastman Kodak by forming a light emitting layer using a complex of small aromatic diamine molecules and aluminum as a material [Appl. Phys. Lett. 51, 913, 1987].

  Organic EL devices convert electrical energy into light when electricity is applied to the organic light emitting material (s). In general, an organic EL device has a structure including an anode, a cathode, and an organic layer disposed between the anode and the cathode. The organic layer of the organic EL device includes a hole injection layer, a hole transport layer, a light emitting layer (including a host material and a dopant material), an electron transport layer, an electron injection layer and the like. Depending on the function, materials for forming the organic layer can be classified into a hole injecting material, a hole transporting material, a light emitting material, an electron transporting material, an electron injecting material and the like. When a voltage is applied to the organic EL device, holes and electrons are injected into the light emitting layer from the anode and the cathode, respectively. High energy excitons are formed by recombination between holes and electrons, and the energy brings the organic light emitting compound into the excited state, which causes relaxation of the energy level to the ground state by attenuation of the excited state. This is accompanied by light emission.

  The most important factor determining the luminous efficiency in the organic EL device is the luminous material. The light emitting material should have high quantum efficiency, high electron mobility, and high hole mobility. Furthermore, the light emitting layer formed by the light emitting material needs to be uniform and stable. Depending on the color to be visualized by luminescence, the luminescent material may be classified as blue, green or red luminescent material, and additionally may comprise yellow or orange luminescent material. Depending on the excited state, luminescent materials can be classified as fluorescent materials (singlet state) and phosphorescent materials (triplet state). Fluorescent materials are widely used in organic EL devices. However, since the phosphorescent material can enhance the luminous efficiency by four times and can reduce the power consumption and prolong the life as compared with the fluorescent material, the development of the phosphorescent light emitting material has been widely studied It is done.

The iridium (III) complex can be prepared by using bis (2- (2'-benzothienyl) -pyridinato-N, C-3 ') iridium (acetylacetonate) ((acac) Ir (btp) ₂ ), tris (2- (2) -benzothienyl) Phenylpyridine) iridium (Ir (ppy) ₃ ) and bis (4,6-difluorophenylpyridinato-N, C2) picolinate iridium (Firpic) are included as red, green and blue light emitting materials respectively , Widely known as phosphorescent materials.

  The light emitting material can be prepared by combining the host material with the dopant to improve color purity, luminous efficiency, and stability. The host material has a significant impact on the efficiency and performance of the EL device when using a host material / dopant system as the light emitting material, so their choice is important. At present, 4,4'-N, N'-dicarbazole-biphenyl (CBP) is the most widely known host material for phosphorescent materials. Recently, Pioneer (Japan) et al. Has been known to host vasocuproin (BCP) and aluminum (III) bis (2-methyl-8-quinolinate) (4-phenylphenolate) (BAlq) etc., which were known as hole blocking materials. We developed a high-performance organic EL device to be used as a material.

  Although these phosphorescent host materials provide good emission characteristics, they have the following disadvantages: (1) due to their low glass transition temperature and low thermal stability, even vacuum and high temperature Their degradation can occur during the deposition process. (2) The power efficiency of the organic EL device is obtained by [(π / voltage) × current efficiency], and this power efficiency is inversely proportional to the voltage. Organic EL devices containing phosphorescent host materials provide higher current efficiencies (cd / A) than those containing fluorescent materials, but require very high drive voltages. Therefore, there is no advantage in terms of power efficiency (lm / W). (3) Furthermore, the operating life of the organic EL device is short, and the luminous efficiency still needs to be improved.

  On the other hand, copper phthalocyanine (CuPc), 4,4'-bis [N- (1-naphthyl) -N-phenylamino] biphenyl (NPB), N, N'-diphenyl-N, N'-bis (3) -Methylphenyl)-(1,1′-biphenyl) -4,4′-diamine (TPD), 4,4 ′, 4 ′ ′-tris (3-methylphenylphenylamino) triphenylamine (MTDATA), etc. It has been used as a hole injection and transport material for organic EL devices However, organic EL devices using these materials have problems in terms of quantum efficiency and lifetime, which means that the organic EL devices have high current Attributable to the thermal stress generated between the anode and the hole injection layer when driven by the thermal stress, which significantly reduces the lifetime of the device. The organic material to be use in order to have a very high hole mobility, the hole - there is a possibility that the balance of the electronic charge is lost, quantum efficiency (cd / A) may be reduced.

  Holes and electrons need to recombine in the light emitting layer in order to prevent the decrease in quantum efficiency and enhance the light emission efficiency. For such improvement of the light emission properties of organic EL devices, it is important to develop hole transport materials and electron transport materials as well as host materials and dopant materials. Therefore, there is a growing interest in organic compounds that efficiently transport holes and electrons from the electrode to the light emitting layer.

  Korean Patent Application Publication Nos. 10-2012-0014913 and 10-2012-0047706 are, respectively, a fluorene derivative as a hole transport compound and a fused heterocycle as a hole injection and transport compound or an electron injection and transport compound. Disclosed are Formula Derivatives. However, it is necessary to develop organic compounds with better current and power efficiency than those of the above mentioned references.

Disclosure of the Invention The object of the present disclosure is to include an organic electroluminescent compound having good hole transport ability and the organic electroluminescent compound of the present disclosure in a hole transport layer, and to improve the current and power efficiency and the lifetime. It is to provide an organic electroluminescent device.

  The present inventors have discovered that the above-mentioned object can be achieved by an organic electroluminescent compound represented by the following formula 1:

During the ceremony
L ₁ represents a single bond, substituted or unsubstituted (C 6 -C 30) arylene, or substituted or unsubstituted (5 to 30 members) heteroarylene,
L ₂ represents a single bond, substituted or unsubstituted (C 6 -C 30) arylene, or substituted or unsubstituted (5 to 30 members) heteroarylene,
Ar ₁ and Ar ₂ each independently represent substituted or unsubstituted (C 6 -C 30) aryl or substituted or unsubstituted (5 to 30 members) heteroaryl,
X is, -O -, - S -, - C (R 1) (R 2) -, or -N _{(R 3)} - represents,
R _{1 to} R ₃ each independently represent hydrogen, deuterium, halogen, cyano, carboxy, nitro, hydroxy, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, Substituted or unsubstituted (C3-C30) cycloalkenyl, substituted or unsubstituted (3-7 membered) heterocycloalkyl, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (5-30 membered) heteroaryl Or R ₁ and R ₂ may be linked to each other to form a (3 to 30 membered) monocyclic or polycyclic, alicyclic or aromatic ring, the carbon thereof The atom (s) may be replaced with at least one heteroatom selected from nitrogen, oxygen and sulfur,
R ₄ to R ₇ are each independently hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (5-30 membered ) Heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (3 to 7-membered) heterocycloalkyl, substituted or unsubstituted (C6-C30) aryl (C1-C30) alkyl, -N (-) R ₁₀ ) (R ₁₁ ), —Si (R ₁₂ ) (R ₁₃ ) (R ₁₄ ), —S (R ₁₅ ), —O (R ₁₆ ), cyano, nitro or hydroxyl, or adjacent The carbon atom (s) may be linked to a substituent (s) to form a (3-30 membered) monocyclic or polycyclic, alicyclic or aromatic ring, and the carbon atom (s) may be nitrogen Oxygen, and it may be replaced with at least one heteroatom selected from sulfur,
R _{10 to} R ₁₆ each independently represent hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (5 to 30 members) 3) Heteroaryl, substituted or unsubstituted (3 to 7 members) heterocycloalkyl, or substituted or unsubstituted (C3-C30) cycloalkyl, or linked to adjacent substituent (s) (3 To 30 members) may form a monocyclic or polycyclic, alicyclic or aromatic ring, and the carbon atom (s) is / are at least one selected from nitrogen, oxygen and sulfur May be replaced with a heteroatom,
Heteroaryl (ene) and heterocycloalkyl each independently contain at least one heteroatom selected from B, N, O, S, P (= O), Si, and P,
Each of a and b independently represents an integer of 1 to 4, and when a or b is an integer of 2 or more, each of R ₅ or each of R ₆ may be the same or different.
c represents an integer of 1 or 2, and when c is 2, each of R ₇ may be the same or different.

  The organic electroluminescent compounds of the present disclosure have excellent hole transport ability. Thus, by including the organic electroluminescent compound of the present disclosure in the hole transport layer, the organic electroluminescent device exhibits an improved current density and a reduced driving voltage, thereby improving the current and power efficiency and the long lifetime. I will provide a.

  The present disclosure will now be described in detail. However, the following description is intended to explain the present disclosure, and is not meant to limit the scope of the present disclosure in any way.

  The present disclosure provides an organic electroluminescent compound of formula 1 as described above, an organic electroluminescent material comprising the same, and an organic electroluminescent device comprising the material.

  As used herein, “(C 1 -C 30) alkyl (ene)” is a linear or branched alkyl having 1 to 30, preferably 1 to 20, and more preferably 1 to 10 carbon atoms. (Ene), which includes methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl and the like. "(C2-C30) alkenyl" represents linear or branched alkenyl having 2 to 30, preferably 2 to 20, and more preferably 2 to 10 carbon atoms, to which vinyl is attached 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 2-methylbut-2-enyl and the like. "(C2-C30) alkynyl" denotes linear or branched alkynyl having 2 to 30, preferably 2 to 20, and more preferably 2 to 10 carbon atoms, to which ethynyl may be attached. 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methylpent-2-ynyl and the like. “(C 3 -C 30) cycloalkyl” represents a monocyclic or polycyclic hydrocarbon having 3 to 30, preferably 3 to 20, and more preferably 3 to 7 carbon atoms, And cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and the like. “(3-7 membered) heterocycloalkyl” refers to at least one heteroatom selected from B, N, O, S, P (= O), Si, and P, preferably O, S, and N. Indicate cycloalkyl having 3 to 7, preferably 5 to 7 ring skeleton atoms, including tetrahydrofuran, pyrrolidine, thiolane, tetrahydropyran and the like. Furthermore, "(C6-C30) aryl (ene)" is derived from an aromatic hydrocarbon and has 6 to 30, preferably 6 to 20, and more preferably 6 to 15 ring skeleton carbon atoms Monocyclic ring or fused ring is shown, such as phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, chrysenyl, naphthacenyl, fluoranthenyl etc. Is included. “(3 to 30 members) heteroaryl (ene)” is at least one, preferably 1 to 4 selected from the group consisting of B, N, O, S, P (= O), Si and P And an aryl group having 3 to 30, preferably 3 to 20, and more preferably 3 to 15 ring skeleton atoms, each having a monocyclic ring or at least one benzene ring It may be a fused ring fused, may be partially saturated, and may be formed by linking at least one heteroaryl or aryl group to a heteroaryl group by a single bond (s), to which Is furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl Monocyclic ring heteroaryls such as tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and benzofuranyl, benzothiophenyl, isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl, benzimidazolyl, benzothiazolyl, benzo Isothiazolyl, benzoisoxazolyl, benzoxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, sinolinyl, quinazolinyl, quinoxalinyl, carbazolyl, phenoxazinyl, phenanthridinyl, benzodioxolyl, etc. These fused ring heteroaryls are included. Further, "halogen" includes F, Cl, Br and I.

In the present specification, "substituted" in the expression "substituted or unsubstituted" means that a hydrogen atom in a specific functional group is replaced with another atom or group, that is, a substituent. In Formula 1 of the present disclosure, substituted alkyl, substituted cycloalkyl, substituted cycloalkenyl, substituted heterocycloalkyl, substituted in L ₁ , L ₂ , Ar ₁ , Ar ₂ , R _{1 to} R ₇ , and R _{10 to} R ₁₆ The substituents of aryl (ene) and substituted heteroaryl (ene) are each independently deuterium, halogen, cyano, carboxy, 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 members) Heterocycloalkyl, (C6-C30) aryloxy, (C6-C30) arylthio, unsubstituted or (C -C30) aryl substituted (3 to 30 members) heteroaryl, unsubstituted or (3 to 30 members) heteroaryl substituted (C 6 to C 30) aryl, tri (C 1 to C 30) alkyl silyl, 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) alkyl carbonyl, (C1-C30) alkoxy carbonyl, (C6-C30) aryl carbonyl, di ( C 6 -C 30) arylcarbonyl, di (C 1 -C 30) alkylboroni Or at least one selected from the group consisting of (C1-C30) alkyl (C6-C30) arylboronyl, (C6-C30) aryl (C1-C30) alkyl, and (C1-C30) alkyl (C6-C30) aryl It is one.

In Formula 1, L ₁ and L ₂ each independently preferably represent a single bond, substituted or unsubstituted (C 6 -C 20) arylene, or substituted or unsubstituted (5 to 20 membered) heteroarylene, Preferably, it represents a single bond, substituted or unsubstituted (C6-C15) arylene, or substituted or unsubstituted (5 to 15 membered) nitrogen-containing heteroarylene. Specifically, L ₁ and L ₂ are each independently a single bond, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted pyridyl , Substituted or unsubstituted pyrimidinyl, substituted or unsubstituted triazinyl, and substituted or unsubstituted fluorenyl. Substituents of L ₁ and L ₂ may be selected from (C 1 -C 10) alkyl, mono or di (C 6 -C 18) arylamino, and (C 6 -C 18) aryl.

In Formula 1, Ar ₁ and Ar ₂ each independently preferably represent substituted or unsubstituted (C 6 -C 20) aryl, or substituted or unsubstituted (5 to 20 membered) heteroaryl, more specifically , Substituted or unsubstituted (C6-C15) aryl or substituted or unsubstituted (5 to 15 membered) nitrogen-containing heteroaryl. Specifically, Ar ₁ and Ar ₂ are each independently substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted Substituted anthranyl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted benzofluorenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted quinolyl, substituted or unsubstituted It may be selected from unsubstituted isoquinolyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, and substituted or unsubstituted phenanthridinyl. Substituents of Ar ₁ and Ar ₂ may be selected from (C 1 -C 10) alkyl, mono or di (C 6 -C 18) arylamino, and (C 6 -C 18) aryl.

In Formula 1, X represents -O-, -S-, -C (R < ₁ >) (R < ₂ >)-, or -N (R < ₃ >)-. R _{1 to} R ₃ each independently preferably represent substituted or unsubstituted (C 1 -C 20) alkyl or substituted or unsubstituted (C 6 -C 20) aryl, and more preferably substituted or unsubstituted (C 1 -C 6) C10) represents alkyl or substituted or unsubstituted (C6-C15) aryl. Specifically, X may represent -O-, -S-, or -C (R < ₁ >) (R < ₂ >)-.

In Formula 1, R ₄ preferably represents substituted or unsubstituted (C 1 -C 20) alkyl, substituted or unsubstituted (C 6 -C 20) aryl, or substituted or unsubstituted (5 to 20 membered) heteroaryl. Preferably, it represents substituted or unsubstituted (C1-C10) alkyl, substituted or unsubstituted (C6-C15) aryl, or substituted or unsubstituted (5-15 membered) nitrogen-containing heteroaryl. Specifically, R ₄ is substituted or unsubstituted (C 1 -C 10) alkyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthrenyl , Substituted or unsubstituted anthranyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted pyridyl, and substituted or unsubstituted pyrimidinyl. Substituents of R ₄ may be selected from (C 1 -C 10) alkyl, mono or di (C 6 -C 18) arylamino, and (C 6 -C 18) aryl.

In Formula 1, each of R _{5 to} R ₇ is preferably independently hydrogen, substituted or unsubstituted (C 1 -C 20) alkyl, substituted or unsubstituted (C 6 -C 20) aryl, substituted or unsubstituted (5 to 6 20 membered) heteroaryl or -N (R ₁₀ ) (R ₁₁ ), more preferably hydrogen, substituted or unsubstituted (C 1 -C 10) alkyl, substituted or unsubstituted (C 6 -C 15) aryl, substituted or substituted an unsubstituted (5-15 membered) nitrogen-containing heteroaryl or _{-N, (R 10) (R} 11). R _{10 to} R ₁₁ each independently preferably represent substituted or unsubstituted (C 6 -C 20) aryl, more preferably substituted or unsubstituted (C 6 -C 15) aryl.

According to one embodiment of the present disclosure, in Formula 1, L ₁ and L ₂ are each independently a single bond, substituted or unsubstituted (C 6 -C 20) arylene, or substituted or unsubstituted (5 to 20 members) Ar ₁ and Ar ₂ may each independently represent substituted or unsubstituted (C 6 -C 20) aryl or substituted or unsubstituted (5 to 20 membered) heteroaryl, R _{1 to} R ₃ Each independently can represent substituted or unsubstituted (C 1 -C 20) alkyl or substituted or unsubstituted (C 6 -C 20) aryl, and R ₄ is substituted or unsubstituted (C 1 -C 20) alkyl, substituted or unsubstituted substituted (C6-C20) aryl or substituted or unsubstituted (5-20 membered) can represent _heteroaryl,, R 5 to R ₇ are each independently, Represents hydrogen, substituted or unsubstituted (C1-C20) alkyl, substituted or unsubstituted (C6-C20) aryl, substituted or unsubstituted (5-20 membered) heteroaryl or _-N, (R 10) a _{(R 11)} R _{10 to} R ₁₁ may independently represent substituted or unsubstituted (C 6 -C 20) aryl.

According to another embodiment of the present disclosure, in Formula 1, L ₁ and L ₂ are each independently a single bond, substituted or unsubstituted (C 6 -C 15) arylene, or substituted or unsubstituted (5 to 15 membered) ) Ar ₁ and Ar ₂ may each independently represent substituted or unsubstituted (C 6 -C 15) aryl or substituted or unsubstituted (5 to 15 membered) nitrogen containing heteroaryl, R _{1 to} R ₃ may each independently represent substituted or unsubstituted (C 1 -C 10) alkyl or substituted or unsubstituted (C 6 -C 15) aryl, and R ₄ may be substituted or unsubstituted (C 1 -C 10) R ₅ -R may represent alkyl, substituted or unsubstituted (C 6 -C 15) aryl, or substituted or unsubstituted (5 to 15 membered) nitrogen containing heteroaryl, ₇ are each independently hydrogen, substituted or unsubstituted (C1-C10) alkyl, substituted or unsubstituted (C6-C15) aryl, substituted or unsubstituted (5-15 membered) nitrogen-containing heteroaryl, or -N (R ₁₀ ) (R ₁₁ ) may be represented, and R _{10 to} R ₁₁ may each independently represent a substituted or unsubstituted (C6-C15) aryl.

According to another embodiment of the present disclosure, in Formula 1, X may represent —O—, —S—, or —C (R ₁ ) (R ₂ ) —, and R ₄ may be substituted or unsubstituted ( C6-C20) aryl or substituted or unsubstituted (5-20 membered) heteroaryl may be represented.

According to another embodiment of the present disclosure, in Formula 1, L ₁ and L ₂ may each independently represent a single bond or (C 6 -C 20) arylene, and X is —O—, —S—, Or -C (R < ₁ >) (R < ₂ >)-, and R < ₄ > may represent substituted or unsubstituted (C6-C20) aryl.

  The compounds of formula 1 may be selected from, but not limited to:

  The organic electroluminescent compounds of the present disclosure can be prepared by synthetic methods known to those skilled in the art. For example, it can be prepared according to the following reaction scheme 1:

In the above reaction scheme 1, X, L _1, L ₂ , Ar ₁ , Ar ₂ , R _{4 to} R ₇ , a, b and c are as defined in the above formula 1, and Hal is halogen Represents

  According to another aspect of the present disclosure, an organic electroluminescent material comprising an organic electroluminescent compound of Formula 1 and an organic electroluminescent device comprising the material are provided. This material may be comprised of the organic electroluminescent compounds of the present disclosure. Otherwise, the material may further include conventional compound (s) contained within the organic electroluminescent material in addition to the compounds of the present disclosure. The organic electroluminescent device of the present disclosure may comprise a first electrode, a second electrode, and at least one organic layer disposed between the first electrode and the second electrode. The organic layer may comprise at least one organic electroluminescent compound of Formula 1.

  One of the first and second electrodes may be an anode and the other may be a cathode. The organic layer may include a light emitting layer, and may further include at least one layer selected from a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, an intermediate layer, and a hole blocking layer. The organic electroluminescent compounds of Formula 1 of the present disclosure can be included in the hole transport layer.

  When used in a hole transport layer, the organic electroluminescent compounds of the present disclosure may be included therein as a hole transport material. When used in a light emitting layer, the organic electroluminescent compounds of the present disclosure may be included therein as a host material.

  An organic electroluminescent device comprising an organic electroluminescent compound of the present disclosure may further comprise at least one host compound other than the organic electroluminescent compound of the present disclosure. Furthermore, the organic electroluminescent device may further comprise at least one dopant.

  The organic electroluminescent compound of the present disclosure may be included in the light emitting layer as a host material (first host material), and another compound may be included as a second host material. The weight ratio of the first host material to the second host material is in the range of 1:99 to 99: 1.

  The second host material can be derived from any of the known phosphorescent host materials. A material selected from the group consisting of compounds of the following formulas 6 to 8 is preferable as the second host material from the viewpoint of luminous efficiency.

  Where Cz represents the following structure:

R _{21 to} R ₂₄ are each independently hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3 to 30 members) ) heteroaryl, or _R 25 _R 26 _R 27 Si- and _represents, R 25 _{to R 27} are each independently a substituted or unsubstituted (C1-C30) alkyl, or substituted or unsubstituted (C6-C30) aryl L ₄ represents a single bond, substituted or unsubstituted (C 6 -C 30) arylene, or substituted or unsubstituted (5 to 30 membered) heteroarylene, and M represents substituted or unsubstituted (C 6 -C 30) aryl or a substituted or unsubstituted (5-30 membered) heteroaryl, _{Y 1} and _{Y 2} are each independently, -O -, - S -, - N ( ₃₁₎ -, or _{-C (R 32) (R 33} ) - represents a proviso, _{Y 1} and _{Y 2,} with the proviso that there is no _{simultaneous,} R 31 _{to R 33} are each independently a substituted Or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (5 to 30 member) heteroaryl, and R ₃₂ and R ₃₃ may be under the same or different And h and i each independently represent an integer of 1 to 3; j, k, o, and p each independently represent an integer of 0 to 4; h, i, j, k And o or p is an integer of 2 or more, each of (Cz-L ₄ ), each of (Cz), each of R ₂₁ , each of R ₂₂ , each of R ₂₃ , or each of R ₂₄ is , Same or different There.

  Specifically, the second host material includes:

  (Wherein, TPS represents triphenylsilyl).

  The dopant of the organic electroluminescent device of the present disclosure is preferably at least one phosphorescent dopant. The phosphorescent dopants of the organic electroluminescent device of the present disclosure are preferably, but not limited to, metallized complex compounds of iridium (Ir), osmium (Os), copper (Cu), or platinum (Pt) It may be selected from ortho-metalated complex compounds of iridium (Ir), osmium (Os), copper (Cu), or platinum (Pt), more preferably ortho-metalated. It may be an iridium complex compound.

  The phosphorescent dopant may preferably be selected from the group consisting of the compounds represented by the following formulas 9-11.

  Where L is selected from the following structure:

R ₁₀₀ represents hydrogen or substituted or unsubstituted (C 1 -C 30) alkyl, and R _{101 to} R ₁₀₉ and R _{111 to} R ₁₂₃ each independently represent hydrogen, deuterium, halogen, unsubstituted or substituted by halogen Or substituted (C1-C30) alkyl, cyano, substituted or unsubstituted (C1-C30) alkoxy, or substituted or unsubstituted (C3-C30) cycloalkyl, or R _{120 to} R ₁₂₃ are adjacent substituents And R _{24 to} R ₁₂₇ each independently may be hydrogen, deuterium, halogen, substituted or unsubstituted (C 1 -C 30). When R represents an alkyl, or substituted or unsubstituted (C6-C30) aryl, and R _{124 to} R ₁₂₇ are aryl, they And ligated with the adjacent substituents (s), fused ring, for example, fluorene, benzofuran or benzothiophene may be _formed, R 201 _{to R 211,} are each independently hydrogen, deuterium, halogen, unsubstituted or substituted by halogen (C1-C30) alkyl, or substituted or unsubstituted (C6-C30) or aryl, or _R 208 _{to R 211,} is connected to the adjacent substituents (s) To form a substituted or unsubstituted (3 to 30 membered) monocyclic or polycyclic, alicyclic or aromatic or heteroaromatic ring, for example, fluorene, dibenzothiophene or dibenzofuran Well, o and p each independently represent an integer of 1 to 3, and when o or p is an integer of 2 or more, each of R ₁₀₀ is the same? Or q may be different, and q represents an integer of 1 to 3.

  Specifically, the phosphorescent dopant material comprises:

  According to a further aspect of the present disclosure, a mixture or composition for making an organic electroluminescent device is provided. The mixture or composition comprises a compound of the present disclosure. The mixture or composition can be a mixture or composition for making a light emitting layer or a hole transport layer of an organic electroluminescent device. The mixture or composition may further include, in addition to the compounds of the present disclosure, conventional compound (s) contained in organic electroluminescent devices.

  The organic electroluminescent device of the present disclosure may comprise a first electrode, a second electrode, and at least one organic layer disposed between the first electrode and the second electrode. The organic layer can include a light emitting layer, which can include a mixture or composition for preparing an organic electroluminescent device of the present disclosure.

  The organic electroluminescent device of the present disclosure comprises a compound of Formula 1 in the organic layer. The organic electroluminescent device of the present disclosure may further include at least one compound selected from the group consisting of arylamine compounds and styrylarylamine compounds.

  In the organic electroluminescent device of the present disclosure, the organic layer is a metal of Group 1 of the periodic table, a metal of Group 2, a transition metal of Period 4, a transition metal of Period 5, in addition to the compound of Formula 1. It may further include at least one metal selected from the group consisting of lanthanides and organometallics of d orbital transition elements, or at least one complex compound containing the metal.

  In addition, the organic electroluminescent device of the present disclosure includes at least one light emitting layer including a blue electroluminescent compound, a red electroluminescent compound, or a green electroluminescent compound known in the art in addition to the compound of the present disclosure. By further including, white light can be emitted. If necessary, it may further comprise an orange light emitting layer or a yellow light emitting layer.

In the organic electroluminescent device of the present disclosure, at least one layer (hereinafter, “surface layer”) selected from a chalcogenide layer, a metal halide layer, and a metal oxide layer is one or both of electrode (s) It may be installed on the inner surface (s). Specifically, a chalcogenide (including oxide) layer of silicon or aluminum is preferably disposed on the anode surface of the electroluminescent medium layer, and the metal halide layer and the metal oxide layer are preferably electroluminescent medium It is placed on the cathode surface of the layer. Such surface layers provide operational stability to the organic electroluminescent device. Preferably, the chalcogenide includes SiO _x (1 ≦ x ≦ 2), AlO _x (1 ≦ x ≦ 1.5), SiON, SiAlON, etc., and the metal halide layer is LiF, MgF ₂ , CaF ₂ , rare earth Metal oxides and the like are included, and metal oxides include Cs ₂ O, Li ₂ O, MgO, SrO, BaO, CaO and the like.

  In the organic electroluminescent device of the present disclosure, a mixed region of an electron transport compound and a reducing dopant, or a mixed region of a hole transport compound and an oxidizing dopant may be disposed on at least one surface of a pair of electrodes. . In this case, the electron transport compound is reduced to an anion, which makes it easier to inject and transport electrons from the mixed region into the electroluminescent medium. In addition, the hole transport compound is oxidized to a cation, which makes it easier to inject and transport holes from the mixed region into the electroluminescent medium. Preferably, the oxidizing dopants include various Lewis acids and acceptor compounds, and the reducing dopants include alkali metals, alkali metal compounds, alkaline earth metals, rare earth metals, and mixtures thereof. The reducing dopant layer can be used as a charge generation layer to fabricate an electroluminescent device having two or more light emitting layers and emitting white light.

  In order to form each layer of the organic electroluminescent device of the present disclosure, dry film formation methods such as vacuum evaporation, sputtering, plasma and ion plating, or inkjet printing, nozzle printing, slot coating, spin coating, dip coating, And wet film formation methods such as flow coating methods may be used.

  When a wet film formation method is used, a thin layer can be formed by dissolving or diffusing the material forming each layer in any suitable solvent such as ethanol, chloroform, tetrahydrofuran, dioxane and the like. The solvent may be any solvent in which materials forming each layer can be dissolved or diffused, and has no problem in film forming ability.

  The compounds of the present disclosure, methods of preparing the compounds, and luminescent properties of the devices will now be described in detail with reference to the following examples.

  Example 1: Preparation of compound C-3

Preparation of Compound 1-1 31 g (130 mmol) of 1,2-dibromobenzene, 25 g (120 mmol) of 4-dibenzofuranboronic acid, 4.1 g (3.54 mmol) of tetrakis (triphenylphosphine) palladium [Pd (PPh ₃ ) ₄ ] After introducing 31 g (295 mmol) of sodium carbonate, 600 mL of toluene, and 150 mL of ethanol into the reaction vessel, 150 mL of distilled water was added thereto. The mixture was stirred at 120 ° C. for 6 hours. After the reaction was complete, the mixture was washed with distilled water and extracted with ethyl acetate. The extracted organic layer was dried over magnesium sulfate and the solvent was removed therefrom by rotary evaporation. The product was purified by column chromatography to give compound 1-1 (22 g, 59%).

Preparation of Compounds 1-2 and 1-3 After introducing 22 g (69 mmol) of Compound 1-1 and 250 mL of tetrahydrofuran into a reaction vessel, the mixture is cooled to −78 ° C. under a nitrogen atmosphere, and then 33 mL of n-butyl lithium (2.5 M, 83 mmol) was slowly dropped into it. The mixture was stirred at -78 ° C for 2 hours and then 4-bromobenzophenone dissolved in 250 mL of tetrahydrofuran was slowly added dropwise thereto. After the addition, the mixture was slowly warmed to room temperature and then further stirred for 30 minutes. After adding ammonium chloride aqueous solution to the reaction mixture to complete the reaction, the mixture was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate and then the solvent was removed by rotary evaporation to give compound 1-2. After adding 700 mL of acetic acid and 0.5 mL of HCl to the obtained compound 1-2, the mixture was stirred at 120 ° C. overnight. After removing the solvent by rotary evaporation, the product was purified by column chromatography to give compound 1-3 (22 g, 65%).

  Preparation of compound C-3

8 g (16.41 mmol) of the compound 1-3, 4- (naphthalen-2-yl) -N-phenylaniline 4.8 g (16.41 mmol), palladium (II) acetate [Pd (OAc ₂ )] 0.15 g (0.66 mmol), 0.8 mL (50%, 1.64 mmol) of tri-t-butylphosphine [P (tBu) ₃ ], 2.4 g (24.62 mmol) of sodium tert-butoxide (NaOtBu), and o- After introducing 80 mL of xylene into the reaction vessel, the mixture was refluxed for 2 hours. The reaction mixture was cooled to room temperature and filtered. The resulting solid was washed with methylene chloride (MC). The filtrate was distilled under reduced pressure and purified by column chromatography to give compound C-3 (5.9 g, 51%).

Example 2 Preparation of Compound C-1 6 g (12.31 mmol) of Compound 1-3, 4 g (12.31 mmol) of di ([1,1′-biphenyl] -4-yl) amine, palladium (II) acetate 0.11 g (0.50 mmol), 0.5 mL (50%, 1.00 mmol) of tri-t-butylphosphine, 1.8 g (18.47 mmol) of sodium tert-butoxide, and 62 mL of o-xylene are introduced into a reaction vessel After the mixture was allowed to reflux for 2 hours. The reaction mixture was cooled to room temperature and filtered. The resulting solid was washed with methylene chloride (MC). The filtrate was distilled under reduced pressure and purified by column chromatography to give the compound (1.7 g, 19%).

Example 3 Preparation of Compound C-25 7 g (14.36 mmol) of compound 1-3, 4-([1,1′-biphenyl] -4-yl (phenyl) amino) boronic acid 6.3 g (17. 23 mmol), 0.5 g (0.43 mmol) of tetrakis (triphenylphosphine) palladium, 3.8 g (35.90 mmol) of sodium carbonate, 72 mL of toluene, and 18 mL of ethanol are introduced into a reaction vessel, followed by 18 mL of distilled water Added. The mixture was stirred at 120 ° C. for 6 hours. After the reaction was complete, the mixture was washed with distilled water and extracted with ethyl acetate. The extracted organic layer was dried over magnesium sulfate. After removing the solvent by rotary evaporation, the product was purified by column chromatography to give compound C-25 (25.2 g, 50%).

  Example 4: Preparation of compound C-38

Preparation of Compound 2-1 30 g (132 mmol) of dibenzo [b, d] thiophen-4-ylboronic acid, 74 g (263 mmol) of 1-bromo-2-iodobenzene, 7.6 g (6.5 mmol) of tetrakis (triphenylphosphine) palladium After introducing 36.3 g (263 mmol) of potassium carbonate, 900 mL of toluene, and 130 mL of ethanol into the reaction vessel, the mixture was stirred at 120 ° C. for 12 hours. After cooling the reaction mixture to room temperature, the cooled mixture was diluted with ethyl acetate, washed with distilled water and then dried over anhydrous magnesium sulfate. After removing the solvent by rotary evaporation, the product was purified by column chromatography to give compound 2-1 (29 g, 56%).

Preparation of Compound 2-2 After dissolving 29.2 g (86.1 mmol) of Compound 2-1 in 500 mL of tetrahydrofuran, 51.6 mL (2.5 M in hexane) of n-butyllithium was slowly added at -78 ° C. And added there. After 1 hour, 22.4 g (103 mmol) of (4-chlorophenyl) (phenyl) methanone dissolved in 100 mL of tetrahydrofuran were slowly added to the mixture. The mixture was allowed to warm to room temperature and then stirred for 12 hours. After the reaction was complete, the mixture was washed with distilled water, extracted with ethyl acetate and then dried over magnesium sulfate. After removing the solvent by rotary evaporation, the product was purified by column chromatography to give compound 2-2 (28 g, 68%).

Preparation of Compound 2-3 After 28 g (58.7 mmol) of Compound 2-2, 0.24 mL (2.93 mmol) of hydrochloric acid and 600 mL of acetic acid were introduced into a reaction vessel, the mixture was stirred at 130 ° C. for 12 hours. After the reaction was complete, the mixture was extracted with methylene chloride and then dried over magnesium sulfate. After removing the solvent by rotary evaporation, the product was purified by column chromatography to give compound 2-3 (13 g, 48%).

  Preparation of Compound C-38

7 g (15.2 mmol) of the compound 2-3, 4- (naphthalen-2-yl) -N-phenylaniline 4.9 g (16.8 mmol), tris (dibenzylidene benzene) dipalladium (0) 0.7 g (7.6 mmol) of [Pd ₂ (dba) ₃ ], 0.75 g (18.3 mmol) of S-Phos (2-dicyclohexylphosphino-2 ′, 6′-dimethoxybiphenyl), sodium tert-butoxide 3 After introducing .66 g (38.1 mmol) and 100 mL of o-xylene into the reaction vessel, the mixture was stirred at 180 ° C. for 1 hour and then cooled to room temperature. The cooled mixture was diluted with ethyl acetate, washed several times with water and then dried over anhydrous magnesium sulfate. After removing the solvent by rotary evaporation, the product was purified by column chromatography to give compound C-38 (1.8 g, 16%).

Example 5 Preparation of Compound C-36 6 g (13.1 mmol) of compound 2-3, di ([1,1′-biphenyl] -4-yl) amine 4.62 g (14.4 mmol), tris (di) (Benzyl lindane acetone) 0.6 g (0.65 mmol) of dipalladium (0), 0.64 g (1.57 mmol) of S-Phos, 3.14 g (32.7 mmol) of sodium tert-butoxide, and 90 mL of o-xylene The mixture was stirred at 180.degree. C. for 1 hour and then cooled to room temperature. The cooled mixture was diluted with ethyl acetate, washed with distilled water and then dried over anhydrous magnesium sulfate. After removing the solvent by rotary evaporation, the product was purified by column chromatography to give compound C-36 (3.0 g, 31%).

Example 6: Preparation of compound C-11 7.3 g (15.07 mmol) of compound 1-3, 9,9-Dimethyl-N-phenyl-9H-fluoren-2-amine 4.3 g (15.07 mmol), 0.13 g (0.60 mmol) of palladium (II) acetate, 0.7 mL (50%, 1.51 mmol) of tri-t-butylphosphine, 2.2 g (22.61 mmol) of sodium tert-butoxide, and 75 mL of o-xylene Was introduced into the reaction vessel and the mixture was then refluxed for 2 hours. The reaction mixture was cooled to room temperature and filtered. The resulting solid was washed with methylene chloride. The filtrate was distilled under reduced pressure and then purified by column chromatography to give compound C-11 (4 g, 38%).

  Example 7: Preparation of compound C-98

Preparation of Compound 3-3 After introducing Compound 1-1 (10 g, 30.9 mmol) and 125 mL of tetrahydrofuran into a reaction vessel, the mixture is cooled to −78 ° C. under a nitrogen atmosphere, and then 13 mL of n-butyl lithium (2 .5 M, 34.0 mmol) was slowly dropped into it. The mixture was stirred at -78 ° C for 1 hour, and 3-bromobenzophenone (8.4 g, 32.4 mmol) dissolved in 40 mL of tetrahydrofuran was slowly added dropwise thereto. After addition, the mixture was slowly warmed to room temperature and then further stirred for 16 hours. After adding ammonium chloride aqueous solution to the reaction mixture to complete the reaction, the mixture was extracted with ethyl acetate. The extracted organic layer was dried over magnesium sulfate and then the solvent was removed therefrom by rotary evaporation to give compound 3-2. After adding 200 mL of acetic acid and 0.3 mL of HCl to the obtained compound 3-2, the mixture was stirred at 120 ° C. overnight. After removing the solvent by rotary evaporation, the product was purified by column chromatography to give compound 3-3 (12 g, 80%).

Preparation of Compound C-98 Compound 1-3 (5.5 g, 11.2 mmol), bisbiphenylamine (3.6 g, 11.2 mmol), palladium acetate (0.1 g, 0.45 mmol), S-Phos (0) After introducing .4 g, 1.12 mmol), sodium tert-butoxide (2.7 g, 28.2 mmol), and 60 mL of toluene into the reaction vessel, the mixture was refluxed for 1 hour. After the reaction was complete, the mixture was washed with distilled water and then extracted with methylene chloride (MC). The extracted organic layer was dried over magnesium sulfate. After removing the solvent by rotary evaporation, the product was purified by column chromatography to give compound C-98 (7 g, 86%).

  Physical properties of the compounds prepared in Examples 1-7 are shown in Table 1 below.

Device Example 1 OLED Using the Compound of the Present Disclosure
OLEDs were prepared as follows using the compounds of the present disclosure. Transparent electrode indium tin oxide (ITO) thin film (10 Ω / sq) (Geomatec) on glass substrate for organic light emitting diode (OLED) was subjected to ultrasonic cleaning with acetone and isopropanol and then stored in isopropanol . The ITO substrate was then placed on the substrate holder of the vacuum deposition apparatus. ^{N 1, N 1 '- (} [1,1'- biphenyl] -4,4'-diyl) bis ^{(N 1} - ^{(naphthalen-1-yl)} -N ^{4, N} 4 - diphenyl-1,4 The diamine) was introduced into the cell of the vacuum deposition apparatus and then the pressure in the chamber of the apparatus was controlled to 10 ^-6 Torr. A current was then applied to the cell to evaporate the above introduced material, thereby forming a hole injection layer having a thickness of 60 nm on the ITO substrate. Compound C-25 is then introduced into another cell of the vacuum deposition apparatus and evaporated by applying a current to the cell, whereby a hole transport layer having a thickness of 20 nm on the hole injection layer is obtained. It formed. Thereafter, Compound H-1 was introduced as a host material into one cell of a vacuum deposition apparatus, and Compound D-1 was introduced as a dopant into another cell. As a result of evaporating the two materials at different rates, the dopant is deposited at a doping amount of 15% by weight based on the host and dopant free weight to form a light emitting layer having a thickness of 30 nm on the hole transport layer The

2- (4- (9,10-di (naphthalen-2-yl) anthracene-2-yl) phenyl) -1-phenyl-1H-benzo [d] imidazole is then introduced into one cell, quinoline Lithium acid was introduced into another cell. As a result of evaporating the two materials at the same rate, they were each deposited with a doping amount of 50% by weight to form an electron transport layer having a thickness of 30 nm on the light emitting layer. After depositing lithium quinolinate as an electron injection layer having a thickness of 2 nm on the electron transport layer, an Al cathode having a thickness of 150 nm was then deposited on the electron injection layer by another vacuum deposition apparatus . Thus, the OLED was manufactured. All materials used to make the OLEDs were purified by vacuum sublimation at 10 ^-6 torr. The manufactured OLED showed green emission with a luminance of 1,300 cd / m ² and a current density of 2.7 mA / cm ² .

Device Example 2 OLED Using the Compound of the Present Disclosure
An OLED was prepared in the same manner as in Device Example 1 except that Compound C-1 was used to form a hole transport layer having a thickness of 20 nm, and Compound H-2 was used as a host material to Compound D- After introducing 78 into the two cells of the vacuum deposition system as dopants, respectively, the two materials were evaporated at different rates so that the dopants were deposited at a 3 wt% doping amount based on the host and dopant shipping costs. Thus, a light emitting layer having a thickness of 30 nm was formed on the hole transport layer. The manufactured OLED showed red light emission having a luminance of 1,500 cd / m ² and a current density of 10.2 mA / cm ² .

Device Example 3 OLED Using the Compound of the Present Disclosure
Device example 1 except that compound C-3 was used to form the hole transport layer and compound H-3 and compound D-3 shown in the table below were used as host material and dopant respectively The OLED was manufactured in the same manner as in The manufactured OLED showed blue emission with a luminance of 900 cd / m ² and a current density of 17.3 mA / cm ² .

Device Example 4 OLED Using the Compound of the Present Disclosure
An OLED was prepared in the same manner as in Device Example 1, except that Compound C-36 was used to form a hole transport film having a thickness of 20 nm. The produced OLED showed green emission with a brightness of 800 cd / m ² and a current density of 1.7 mA / cm ² .

Device Example 5 OLED Using the Compound of the Present Disclosure
An OLED was prepared in the same manner as in Device Example 1, except that Compound C-98 was used to form a hole transport film having a thickness of 20 nm. The manufactured OLED showed green emission with a luminance of 1,100 cd / m ² and a current density of 2.3 mA / cm ² .

Device Example 6 OLED Using the Compound of the Present Disclosure
An OLED was prepared in the same manner as in Device Example 2, except that Compound C-11 was used to form a hole transport layer having a thickness of 20 nm. The manufactured OLED showed red light emission with a luminance of 1,000 cd / m ² and a current density of 6.3 mA / cm ² .

[Device Comparative Example 1] OLED using conventional compound
Using N, N'-di (4-biphenyl) -N, N'-di (4-biphenyl) -4,4'-diaminobiphenyl to form a hole transport layer having a thickness of 20 nm An OLED was manufactured in the same manner as Device Example 1 except for the following. The manufactured OLED showed green emission with a luminance of 10,000 cd / m ² and a current density of 26.5 mA / cm ² .

[Device Comparative Example 2] OLED using conventional compound
Using N, N'-di (4-biphenyl) -N, N'-di (4-biphenyl) -4,4'-diaminobiphenyl to form a hole transport layer having a thickness of 20 nm An OLED was manufactured in the same manner as in Device Example 3, except for: The manufactured OLED showed blue emission with a luminance of 4,000 cd / m ² and a current density of 108.1 mA / cm ² .

[Device Comparative Example 3] OLED using conventional compound
Using N, N'-di (4-biphenyl) -N, N'-di (4-biphenyl) -4,4'-diaminobiphenyl to form a hole transport layer having a thickness of 20 nm An OLED was manufactured in the same manner as Device Example 2 except for the following. The produced OLED showed red light emission with a brightness of 8,000 cd / m ² and a current density of 102.6 mA / cm ² .

[Device Comparative Example 4] OLED using conventional compound
Using N, N-di ([1,1′-biphenyl] -4-yl) -7,7-dimethyl-7H-fluoreno [4,3-b] benzofuran-9-amine (HT-1) An OLED was fabricated in the same manner as Device Example 1, except that a hole transport layer having a thickness of 20 nm was formed. The produced OLED showed green emission with a brightness of 7,000 cd / m ² and a current density of 17.2 mA / cm ² .

  As confirmed by the device examples, the organic electroluminescent compounds of the present disclosure have better luminescent characteristics than conventional compounds. The organic electroluminescent device of the present disclosure exhibits excellent luminous efficiency, particularly current efficiency and power efficiency, and lifetime by using the organic electroluminescent compound of the present disclosure.

Claims (6)

Organic electroluminescent compounds represented by the following formula I,

During the ceremony
L ₁ represents a single bond, substituted or unsubstituted (C 6 -C 30) arylene, or substituted or unsubstituted (5 to 30 members) heteroarylene,
L ₂ represents a single bond, substituted or unsubstituted (C 6 -C 30) arylene, or substituted or unsubstituted (5 to 30 members) heteroarylene,
Ar ₁ and Ar ₂ each independently represent substituted or unsubstituted (C 6 -C 30) aryl or substituted or unsubstituted (5 to 30 members) heteroaryl,
X is, -O -, - S -, - C (R 1) (R 2) -, or -N _{(R 3)} - represents,
R _{1 to} R ₃ each independently represent hydrogen, deuterium, halogen, cyano, carboxy, nitro, hydroxy, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C3-C30) cycloalkyl, Substituted or unsubstituted (C3-C30) cycloalkenyl, substituted or unsubstituted (3-7 membered) heterocycloalkyl, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (5-30 membered) heteroaryl Or R ₁ and R ₂ can be linked to each other and their carbon atom (s) can be replaced by at least one heteroatom selected from nitrogen, oxygen and sulfur (3 to 30 members) And may form a monocyclic or polycyclic, alicyclic or aromatic ring,
R ₄ to R ₇ are each independently hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (5-30 membered ) Heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (3 to 7-membered) heterocycloalkyl, substituted or unsubstituted (C6-C30) aryl (C1-C30) alkyl, -N (-) R ₁₀ ) (R ₁₁ ), —Si (R ₁₂ ) (R ₁₃ ) (R ₁₄ ), —S (R ₁₅ ), —O (R ₁₆ ), cyano, nitro, or hydroxy, or adjacent In conjunction with the substituent (s), the carbon atom (s) may be replaced with at least one heteroatom selected from nitrogen, oxygen and sulfur (3-3 Monocyclic or polycyclic membered), cycloaliphatic, or may form an aromatic ring, however, connected to form the ring, or between R ₄ in R ₄ and L ₁ Not formed between L ₂ ,
R _{10 to} R ₁₆ each independently represent hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (5 to 30 members) 3) Heteroaryl, substituted or unsubstituted (3 to 7 members) heterocycloalkyl, or substituted or unsubstituted (C3-C30) cycloalkyl, or linked to adjacent substituent (s) (3 To 30 members) may form a monocyclic or polycyclic, alicyclic or aromatic ring, and the carbon atom (s) is / are at least one selected from nitrogen, oxygen and sulfur May be replaced with a heteroatom,
The heteroaryl (ene) and the heterocycloalkyl each independently contain at least one hetero atom selected from B, N, O, S, P (= O), Si, and P,
Each of a and b independently represents an integer of 1 to 4, and when a or b is an integer of 2 or more, each of R ₅ or each of R ₆ may be the same or different.
c represents an integer of 1 or 2, and when c is 2, each of R ₇ may be the same or different, from the organic electroluminescent compound. L ₁ and L ₂ each independently represent a single bond, substituted or unsubstituted (C 6 -C 20) arylene, or substituted or unsubstituted (5 to 20 membered) heteroarylene, and Ar ₁ and Ar ₂ each represent Independently, it represents substituted or unsubstituted (C6-C20) aryl or substituted or unsubstituted (5- to 20-membered) heteroaryl, and R _{1 to} R ₃ each independently represent substituted or unsubstituted (C 1 -C 20) And R ₄ represents substituted or unsubstituted (C 1 -C 20) alkyl, substituted or unsubstituted (C 6-C 20) aryl, or substituted or unsubstituted (5 to 6) alkyl) or substituted or unsubstituted (C 6 -C 20) aryl. represents 20-membered) _heteroaryl, R 5 to R ₇ are each independently hydrogen, substituted or unsubstituted (C1-C20) alkyl, Substituted or unsubstituted (C6-C20) aryl, substituted or unsubstituted (5-20 membered) heteroaryl or _{-N, (R 10) (R} 11), R 10 ~R 11 are each independently, The organic electroluminescent compound according to claim 1, which represents substituted or unsubstituted (C6-C20) aryl. X represents -O-, -S-, or -C (R ₁ ) (R ₂ )-, and R ₄ is substituted or unsubstituted (C6-C20) aryl or substituted or unsubstituted (5 to 20 members The organic electroluminescent compound according to claim 1, which represents heteroaryl). Said substituted alkyl, said substituted cycloalkyl, said substituted cycloalkenyl, said substituted heterocycloalkyl, said substituted aryl (in L ₁ , L ₂ , Ar ₁ , Ar ₂ , R _{1 to} R ₇ and R _{10 to} R ₁₆ And substituents of the substituted heteroaryl (ene) are each independently deuterium, halogen, cyano, carboxy, 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) hetero Cycloalkyl, (C6-C30) aryloxy, (C6-C30) arylthio, unsubstituted or 6-C30) aryl substituted (3 to 30 members) heteroaryl, unsubstituted or (3 to 30 members) heteroaryl substituted (C 6 to C 30) aryl, tri (C 1 to C 30) 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) alkyl carbonyl, (C1-C30) alkoxycarbonyl, (C6-C30) aryl carbonyl, di- (C6-C30) arylboronyl, di (C1-C30) alkylboroni Or at least one selected from the group consisting of (C1-C30) alkyl (C6-C30) arylboronyl, (C6-C30) aryl (C1-C30) alkyl, and (C1-C30) alkyl (C6-C30) aryl The organic electroluminescent compound according to claim 1, which is one. The compound of formula 1 is

The organic electroluminescent compound according to claim 1 selected from the group consisting of   An organic electroluminescent device comprising the organic electroluminescent compound of claim 1.