Organic electroluminescent compound and organic electroluminescent device comprising same

Abstract

The invention relates to an organic electroluminescent compound and an organic electroluminescent device comprising the same. Provided is an organic electroluminescent compound represented by the following formula 4 or 5: # imgabs0 #

Description

[0001] This invention patent application is a divisional application of the invention patent application with international application number PCT / KR2016 / 008476, international application date August 2, 2016, Chinese national phase application number 201680049101.5, and title “Organic electroluminescent compounds and organic electroluminescent devices comprising the same”. Technical Field

[0002] The present disclosure relates to organic electroluminescent compounds and organic electroluminescent devices comprising the compounds. Background Art

[0003] An electroluminescent (EL) device is a self-luminescent device that has the advantages of providing a wider viewing angle, a higher contrast ratio, and a faster response time. Organic EL devices were originally developed by Eastman Kodak using aromatic diamine small molecules and aluminum complexes as materials for forming a light-emitting layer [Appl. Phys. Lett. 51, 913, 1987].

[0004] When electric energy is applied to an organic light-emitting material, an organic EL device (OLED) converts electric energy into light. In general, an organic EL device has a structure comprising 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, an electron blocking layer, a light-emitting layer (comprising a host material and a doping material), an electron buffer layer, a hole blocking layer, an electron transport layer, an electron injection layer, etc. Depending on its function, the material used to form the organic layer can be classified into a hole injection material, a hole transport material, an electron blocking material, a light-emitting material, an electron buffer material, a hole blocking material, an electron transport material, an electron injection material, etc. 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. Excitons with high energy are formed by the recombination between holes and electrons, and the energy puts the organic light-emitting compound in an excited state, and the decay of the excited state causes the energy level to relax to the ground state and is accompanied by luminescence.

[0005] The most important factor determining the luminous efficiency in an organic EL device is the luminescent material. The luminescent material needs to have high quantum efficiency, high electron mobility and high hole mobility. In addition, the luminescent layer formed by the luminescent material needs to be uniform and stable. Depending on the color visible from the light emission, the luminescent material can be classified as a blue, green or red light emitting material, and may additionally include a yellow or orange light emitting material. In addition, the luminescent material can be classified into a host material and a doping material according to its function. Recently, there is an urgent need to develop an OLED that provides high efficiency and a long service life. Specifically, considering that EL requires medium or large-sized OLED panels, it is necessary to urgently develop materials that show better performance than conventional materials. In order to achieve development, the host material that acts as a solid solvent and can transfer energy should have high purity and appropriate molecular weight for deposition in a vacuum. In addition, the host material should have a high glass transition temperature and a high thermal decomposition temperature to ensure thermal stability; high electrochemical stability to ensure a long service life; easy preparation of amorphous films; and good adhesion to adjacent layer materials. In addition, the host material should not move to the adjacent layer.

[0006] Japanese Patent Application Publication No. 2014-160813 discloses a nitrogen-containing heterocyclic compound formed by condensing a pyrrole ring, an aromatic ring and a 7-membered ring, and an organic electroluminescent element comprising the same. However, the patent application publication does not disclose the compound of the present invention, but discloses a compound in which an aromatic group is fused to the main chain or the fusion position is different from that of the compound of the present invention.

[0007] Based on a study aimed at finding novel compounds that can provide organic electroluminescent devices with superior performance compared to conventional organic light-emitting compounds, the present inventors have found that the present compounds can provide good device performance, including high luminous efficiency and power efficiency. Summary of the invention

[0008] Technical issues

[0009] An object of the present invention is to provide an organic electroluminescent compound which can be effectively used to prepare an organic electroluminescent device having a low driving voltage, good luminescence and power efficiency, and a significantly improved lifetime.

[0010] Problem Solution

[0011] Based on earnest studies conducted to solve the above problems, the present inventors found that the above object can be achieved by an organic electroluminescent compound represented by the following Formula 1 and finally completed the present invention.

[0012]

[0013] In formula 1,

[0014] Each of two adjacent * of a benzene ring of Formula 1 is bonded to each of two * of Formula 2, and

[0015] In equation 1 and equation 2,

[0016] R1 to R5 each independently represent hydrogen, deuterium, halogen, cyano, carboxyl, nitro, hydroxyl, 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, substituted or unsubstituted (3-30 membered) heteroaryl, -NR6R7 or -SiR8R9R 10 , or may be bonded to an adjacent substituent to form a substituted or unsubstituted (C3-C30) monocyclic or polycyclic alicyclic ring or aromatic ring, the carbon atoms of which may be replaced by at least one heteroatom selected from nitrogen, oxygen and sulfur; and

[0017] R6 to R 10 each independently represents hydrogen, deuterium, halogen, cyano, carboxyl, nitro, hydroxyl, 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 (3-30 membered)heteroaryl;

[0018] Ar1 represents a substituted or unsubstituted (C6-C30) aryl group or a substituted or unsubstituted (3- to 30-membered) heteroaryl group;

[0019] a, c, d and e each independently represent an integer from 1 to 4; b represents an integer from 1 to 3; and

[0020] The heteroaryl group contains at least one heteroatom selected from B, N, O, S, Si and P.

[0021] Beneficial effects of the present invention

[0022] The organic electroluminescent compound of the present invention has the following advantages: when used as a host of a light-emitting layer, it can provide an organic electroluminescent device with a low driving voltage and significantly improved luminous efficiency and service life compared to conventional organic light-emitting compounds. Specifically, the organic electroluminescent compound of the present invention can provide an organic electroluminescent device with a low driving voltage and high current and power efficiency. DETAILED DESCRIPTION

[0023] Hereinafter, the present disclosure will be described in detail. However, the following description is intended to explain the present disclosure, rather than to limit the scope of the present disclosure in any way.

[0024] The present disclosure provides an organic electroluminescent compound of Formula 1 above, an organic electroluminescent material including the compound, and an organic electroluminescent device including the material.

[0025] In Formula 1 and Formula 2, R1 to R5 each independently represent hydrogen, deuterium, halogen, cyano, carboxyl, nitro, hydroxyl, 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, substituted or unsubstituted (3-30 membered) heteroaryl, -NR6R7 or -SiR8R9R 10 , or may be bonded to an adjacent substituent to form a substituted or unsubstituted (C3-C30) monocyclic or polycyclic alicyclic ring or aromatic ring, the carbon atoms of which may be replaced by at least one heteroatom selected from nitrogen, oxygen and sulfur; preferably, each independently may represent hydrogen, deuterium, substituted or unsubstituted (C1-C20) alkyl, substituted or unsubstituted (C3-C20) cycloalkyl, substituted or unsubstituted (C3-C20) cycloalkenyl, substituted or unsubstituted (C6-C20) aryl, substituted or unsubstituted (3-20 membered) heteroaryl or -NR6R7, or may be bonded to an adjacent substituent to form a substituted or unsubstituted (C3-C20) monocyclic or polycyclic alicyclic ring or aromatic ring, the carbon atoms of which may be replaced by at least one heteroatom selected from nitrogen, oxygen and sulfur; more preferably, each independently may represent hydrogen, or an unsubstituted (C6-C18) aryl group, or may be bonded to an adjacent substituent to form an unsubstituted (C3-C18) monocyclic or polycyclic aromatic ring; and specifically, each independently may represent hydrogen or an unsubstituted phenyl group, or may be bonded to an adjacent substituent to form an unsubstituted benzene ring.

[0026] In equations 1 and 2, R6 to R 10 Each independently represents hydrogen, deuterium, halogen, cyano, carboxyl, nitro, hydroxyl, 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 (3-30 membered)heteroaryl; preferably, each independently may represent substituted or unsubstituted (C1-C20)alkyl, substituted or unsubstituted (C3-C20)cycloalkyl, substituted or unsubstituted (C3-C20)cycloalkenyl, substituted or unsubstituted (C6-C20)aryl, or substituted or unsubstituted (3-20 membered)heteroaryl.

[0027] In Formula 2, Ar1 represents a substituted or unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted (3-30 membered) heteroaryl group; preferably, a substituted or unsubstituted (C6-C25)aryl group, or a substituted or unsubstituted (3-25 membered) heteroaryl group; more preferably, a substituted or unsubstituted (C6-C25)aryl group, or a substituted or unsubstituted (5-20 membered) heteroaryl group containing nitrogen, oxygen or sulfur; specifically, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted phenylnaphthyl, substituted or unsubstituted naphthylphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted pyridinyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinolyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted The dibenzofuranyl or substituted or unsubstituted dibenzothiophenyl group, wherein the substituent may be at least one selected from the following: (C1-C10) alkyl, phenyl, biphenyl, naphthyl, anthracenyl, terphenyl, phenylnaphthyl, naphthylphenyl, fluorenyl substituted or unsubstituted by (C1-C10) alkyl or (C6-C30) aryl, pyridyl substituted or unsubstituted by (C1-C10) alkyl or (C6-C30) aryl, pyrimidinyl substituted or unsubstituted by (C1-C10) alkyl or (C6-C30) aryl, C1-C10)alkyl or (C6-C30)aryl substituted or unsubstituted triazinyl, (C1-C10)alkyl or (C6-C30)aryl substituted or unsubstituted quinolyl, (C1-C10)alkyl or (C6-C30)aryl substituted or unsubstituted isoquinolyl, (C1-C10)alkyl or (C6-C30)aryl substituted or unsubstituted quinoxalinyl, (C1-C10)alkyl or (C6-C30)aryl substituted or unsubstituted quinazolinyl, and di(C6-C30)arylamino.

[0028] In Formulae 1 and 2, a, c, d and e each independently represent an integer of 1 to 4; b represents an integer of 1 to 3. Preferably, a to e each independently may represent 1 or 2.

[0029] The compounds of formula 1 of the present invention can be represented by the following formulas 3 to 6:

[0030]

[0031] In Formulae 3 to 6, f and g each independently represent an integer of 1 or 2.

[0032] In Formulae 3 to 6, R1 to R5, Ar1, a, b, c, d and e are as defined in Formula 1 above.

[0033] Herein, "(C1-C30) alkyl" refers to a straight or branched alkyl group having 1 to 30, preferably 1 to 20, and more preferably 1 to 10 carbon atoms, and includes methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, etc. "(C2-C30) alkenyl" refers to a straight or branched alkenyl group having 2 to 30, preferably 2 to 20, and more preferably 2 to 10 carbon atoms, and includes vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 2-methylbut-2-enyl, etc. "(C2-C30) alkynyl" refers to a straight or branched alkynyl group having 2 to 30, preferably 2 to 20, and more preferably 2 to 10 carbon atoms, and includes ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methylpent-2-ynyl, etc. Herein, "(C1-C30) alkoxy" refers to a straight or branched alkoxy group having 1 to 30, preferably 1 to 20, and more preferably 1 to 10 carbon atoms, and includes methoxy, ethoxy, propoxy, isopropoxy, 1-ethylpropoxy, etc. Herein, "(C3-C30) cycloalkyl" refers to a monocyclic or polycyclic hydrocarbon having 3 to 30, preferably 3 to 20, and more preferably 3 to 7 ring main chain carbon atoms. Cycloalkyl includes cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc. Herein, "(3 to 7 membered) heterocycloalkyl" refers to a cycloalkyl group having 3 to 7 ring backbone atoms, the ring backbone atoms including at least one heteroatom selected from B, N, O, S, Si and P, preferably O, S and N, and including pyrrolidine, thiolane, tetrahydropyran and the like. Herein, "(C6-C30) (sub)aryl" refers to a monocyclic or condensed ring group derived from an aromatic hydrocarbon having 6 to 30, preferably 6 to 20, more preferably 6 to 15 ring backbone carbon atoms. The aryl group may include an aryl group having a spiro structure. The aryl group includes phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, indenyl, triphenylene, pyrenyl, naphthyl, peryl, chrysene, condensed tetraphenyl, fluoranthenyl and the like.Herein, "(3 to 30 membered) (sub)heteroaryl" refers to an aryl group having 3 to 30, preferably 3 to 20, more preferably 3 to 15 ring main chain atoms, wherein the ring main chain atoms include at least one, preferably 1 to 4 heteroatoms selected from the group consisting of: B, N, O, S, Si and P; may be a monocyclic ring, or a condensed ring condensed with at least one benzene ring; may be partially saturated; may be a group formed by bonding at least one heteroaryl or aryl to a heteroaryl via a single bond; and includes monocyclic heteroaryl groups such as furanyl, phenylthio, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazole, The term "halogen" refers to benzofuranyl, benzothiophenyl, isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl, benzimidazolyl, benzothiazolyl, benzisothiazolyl, benzisoxazolyl, benzoxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, phenoxazinyl, phenanthridinyl, benzodioxolyl, etc. In addition, "halogen" includes F, Cl, Br and I.

[0034] In addition, herein, the term "substituted" in the expression "substituted or unsubstituted" means that a hydrogen atom in a functional group is replaced with another atom or group (ie, a substituent). 10In Ar1, the substituents of the substituted (C1-C30) alkyl, substituted (C3-C30) cycloalkyl, substituted (C3-C30) cycloalkenyl, substituted (3-7 membered) heterocycloalkyl, substituted (C6-C30) aryl, substituted (3-30 membered) heteroaryl, and substituted (C3-C30) monocyclic or polycyclic alicyclic ring or aromatic ring are each independently at least one selected from the group consisting of deuterium, halogen, cyano, carboxyl, nitro, hydroxyl, (C1-C30) alkyl, halo (C1-C30) alkyl, (C2-C30) alkenyl, (C2-C30) alkynyl, (C1-C30) alkane oxy, (C1-C30) alkylthio, (C3-C30) cycloalkyl, (C3-C30) cycloalkenyl, (3-7 membered) heterocycloalkyl, (C6-C30) aryloxy, (C6-C30) arylthio, (5-30 membered) heteroaryl substituted or unsubstituted by (C6-C30) aryl, (5-30 membered) heteroaryl substituted or unsubstituted by (C6-C30) aryl, 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)arylborylcarbonyl, di(C1-C30)alkylborylcarbonyl, (C1-C30)alkyl(C6-C30)arylborylcarbonyl, (C6-C30)aryl(C1-C30)alkyl and (C1-C30)alkyl(C6-C30)aryl; preferably, each independently may be unsubstituted (C6-C20)aryl, substituted (C6-C20)aryl, di(C6-C20)arylamino or di(C1-C20)alkyl(C6-C20)aryl-substituted (5 to 20-membered)heteroaryl; more preferably, each independently may be an unsubstituted (C6-C18)aryl, a (5 to 18-membered)heteroaryl substituted by a (C6-C12)aryl, di(C6-C18)arylamino or di(C1-C10)alkyl(C6-C18)aryl group; and more specifically, each independently may be an unsubstituted phenyl, an unsubstituted biphenyl group, a phenyl-substituted triazinyl group, a phenyl-substituted quinoxalinyl group, a di(C6-C18)arylamino or a dimethylfluorenyl group.

[0035] According to one embodiment of the present invention, in Formula 1 and Formula 2, R1 to R5 may each independently represent hydrogen, deuterium, substituted or unsubstituted (C1-C20) alkyl, substituted or unsubstituted (C3-C20) cycloalkyl, substituted or unsubstituted (C3-C20) cycloalkenyl, substituted or unsubstituted (C6-C20) aryl, substituted or unsubstituted (3-20 membered) heteroaryl or -NR6R7, or may be bonded to an adjacent substituent to form a substituted or unsubstituted (C3-C20) monocyclic or polycyclic alicyclic ring or aromatic ring, the carbon atoms of which may be at least one heteroatom selected from nitrogen, oxygen and sulfur; wherein R6 and R7 each independently may represent a substituted or unsubstituted (C1-C20)alkyl, a substituted or unsubstituted (C3-C20)cycloalkyl, a substituted or unsubstituted (C3-C20)cycloalkenyl, a substituted or unsubstituted (C6-C20)aryl or a substituted or unsubstituted (3-20 membered)heteroaryl; Ar1 ​​may represent a substituted or unsubstituted (C6-C25)aryl, or a substituted or unsubstituted (3-25 membered)heteroaryl; and a to e each independently may be 1 or 2.

[0036] According to another embodiment of the present invention, in Formula 1 and Formula 2, R1 to R4 may each independently represent hydrogen; R5 may represent hydrogen, or an unsubstituted (C6-C18)aryl group, or may be bonded to an adjacent substituent to form an unsubstituted (C3-C18) monocyclic or polycyclic aromatic ring; Ar1 ​​may represent a substituted or unsubstituted (C6-C25)aryl group, or a substituted or unsubstituted (5 to 20 membered) heteroaryl group; a, c, d and e may be 1; and b may be 2.

[0037] More specifically, the organic electroluminescent compounds of Formula 1 disclosed herein include the following, but are not limited thereto:

[0038]

[0039]

[0040]

[0041] In addition, the present disclosure provides an organic electroluminescent material including the organic electroluminescent compound of Formula 1, and an organic electroluminescent device including the material.

[0042] The material may consist only of the organic electroluminescent compound of the present disclosure. In addition, in addition to the compound described in the present disclosure, the material may further contain conventional compounds that have been contained in organic electroluminescent materials.

[0043] The organic electroluminescent device of the present disclosure may include a first electrode, a second electrode, and at least one organic layer disposed between the first and second electrodes. The organic layer may include at least one organic electroluminescent compound of Formula 1.

[0044] One of the first electrode and the second electrode 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 the following: a hole injection layer, a hole transport layer, a hole auxiliary layer, an auxiliary light-emitting layer, an electron transport layer, an electron buffer layer, an electron injection layer, an intermediate layer, a hole blocking layer, and an electron blocking layer, wherein the hole auxiliary layer or the auxiliary light-emitting layer is inserted between the hole transport layer and the light-emitting layer, and adjusts the hole mobility. The hole auxiliary layer or the auxiliary light-emitting layer has the function of providing improved efficiency and service life for the organic electroluminescent device.

[0045] The organic electroluminescent compound of Formula 1 of the present disclosure may be included in the light emitting layer as a host material. Preferably, the light emitting layer may further include at least one dopant, and if necessary, may further include a compound other than the organic electroluminescent compound of Formula 1 of the present disclosure as a second host material.

[0046] According to another aspect of the present disclosure, it provides a material for preparing an organic electroluminescent device. The material may include a first host material and a second host material, wherein the first host material includes the organic electroluminescent compound of the present disclosure. The weight ratio between the first host material and the second host material is in the range of 1:99 to 99:1.

[0047] The second host material may be selected from any known phosphorescent host material. Preferably, the second host material may be selected from the group consisting of phosphorescent host materials of Formulae 7 to 11 below.

[0048] H-(Cz-L4) i -M(7)

[0049] H-(Cz) j -L4-M(8)

[0050]

[0051] in

[0052] Cz has the following structure:

[0053]

[0054] A represents -O- or -S-;

[0055] R 21 to R 24each independently represents hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (5-30 membered) heteroaryl, or -SiR 25 R 26 R 27 ; R 25 to R 27 each independently represents a substituted or unsubstituted (C1-C30) alkyl group or a substituted or unsubstituted (C6-C30) aryl group; L4 represents a single bond, a substituted or unsubstituted (C6-C30) arylene group, or a substituted or unsubstituted (5- to 30-membered) heteroarylene group; M represents a substituted or unsubstituted (C6-C30) aryl group or a substituted or unsubstituted (5- to 30-membered) heteroaryl group; Y1 and Y2 each independently represent -O-, -S-, -N(R 41 )-or-C(R 42 )(R 43 )-, and Y1 and Y2 do not exist at the same time; R 41 to R 43 each independently represents a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted (5- to 30-membered)heteroaryl group, R 42 and R 43 may be the same or different; i and j each independently represent an integer from 1 to 3; k, l, m and n each independently represent an integer from 0 to 4; when i, j, k, l, m or n is an integer of 2 or more, each (Cz-L4), each (Cz), each R 21 , each R 22 , each R 23 or each R 24 Can be the same or different.

[0056] Specifically, the second main material preferably includes the following:

[0057]

[0058]

[0059] [Wherein, TPS represents triphenylsilyl.]

[0060] The dopant contained in the organic electroluminescent device of the present disclosure is preferably at least one phosphorescent dopant. The phosphorescent dopant material used for the organic electroluminescent device of the present disclosure is not limited, but can be preferably selected from metallized complex compounds of iridium (Ir), osmium (Os), copper (Cu) or platinum (Pt), more preferably selected from ortho-metallized complex compounds of iridium (Ir), osmium (Os), copper (Cu) or platinum (Pt), and even more preferably ortho-metallized iridium complex compounds.

[0061] The compounds represented by the following Formulae 101 to 103 may be used as a dopant to be included in the organic electroluminescent device of the present disclosure.

[0062]

[0063] Where L d Select from the following structures:

[0064]

[0065] R 100 represents hydrogen, substituted or unsubstituted (C1-C30)alkyl or substituted or unsubstituted (C3-C30)cycloalkyl;

[0066] R 101 to R 109 and R 111 to R 123 R each independently represents hydrogen, deuterium, halogen, halogen-substituted or unsubstituted (C1-C30)alkyl, cyano, substituted or unsubstituted (C1-C30)alkoxy, substituted or unsubstituted (C6-C30)aryl or substituted or unsubstituted (C3-C30)cycloalkyl; 106 to R 109 Each independently may be bonded to an adjacent substituent to form a substituted or unsubstituted condensed ring, such as alkyl-substituted or unsubstituted fluorene, alkyl-substituted or unsubstituted dibenzothiophene, or alkyl-substituted or unsubstituted dibenzofuran; R 120 to R 123 Each independently may be bonded to an adjacent substituent to form a substituted or unsubstituted fused ring, such as alkyl or aryl substituted or unsubstituted quinoline;

[0067] R 124 to R 127 Each independently represents hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl or substituted or unsubstituted (C6-C30) aryl; R 124 to R 127Each independently may be bonded to an adjacent substituent to form a substituted or unsubstituted fused ring, such as an alkyl-substituted or unsubstituted fluorene, an alkyl-substituted or unsubstituted dibenzothiophene, or an alkyl-substituted or unsubstituted dibenzofuran;

[0068] R 201 to R 211 Each independently represents hydrogen, deuterium, halogen, halogen-substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C3-C30)cycloalkyl or substituted or unsubstituted (C6-C30)aryl; R 201 to R 211 Each independently may be bonded to an adjacent substituent to form a substituted or unsubstituted fused ring, such as an alkyl-substituted or unsubstituted fluorene, an alkyl-substituted or unsubstituted dibenzothiophene, or an alkyl-substituted or unsubstituted dibenzofuran;

[0069] r and s each independently represent an integer from 1 to 3; when r or s is an integer of 2 or more, each R 100 may be the same or different; and

[0070] t represents an integer from 1 to 3.

[0071] Specifically, phosphorescent dopants include the following:

[0072]

[0073]

[0074]

[0075]

[0076]

[0077] The organic electroluminescent device of the present disclosure includes the organic electroluminescent compound of Formula 1, and may further include at least one compound selected from the group consisting of arylamine-based compounds and styrylarylamine-based compounds.

[0078] In the organic electroluminescent device of the present disclosure, in addition to the compound of Formula 1, the organic layer may further include at least one metal selected from the group consisting of: metals of Group 1, Group 2, transition metals of Period 4, transition metals of Period 5, lanthanide elements, and organometallics of d-transition elements of the periodic table, or at least one complex compound containing the metal. The organic layer may further include a light-emitting layer and a charge generating layer.

[0079] In addition, the organic electroluminescent device of the present disclosure can emit white light by further comprising at least one light-emitting layer, wherein the light-emitting layer further comprises a blue light-emitting compound, a red light-emitting compound or a green light-emitting compound known in the art in addition to the compound of the present disclosure. Optionally, the light-emitting layer may further comprise an orange light-emitting layer or a yellow light-emitting layer.

[0080] In the organic electroluminescent device of the present disclosure, preferably, at least one layer (hereinafter referred to as "surface layer") may be placed on the inner surface of one or both electrodes, the layer being selected from a chalcogenide layer, a metal halide layer, and a metal oxide layer. Specifically, a chalcogenide (including oxide) layer of silicon or aluminum is preferably placed on the anode surface of the electroluminescent medium layer, and a metal halide layer or a metal oxide is preferably placed on the cathode surface of the electroluminescent medium layer. Such a surface layer provides operational stability for the organic electroluminescent device. Preferably, the chalcogenide comprises SiO X (1≤X≤2), AlO X (1≤X≤1.5), SiON, SiAlON, etc.; metal halides include LiF, MgF2, CaF2, rare earth metal fluorides, etc.; and metal oxides include Cs2O, Li2O, MgO, SrO, BaO, CaO, etc.

[0081] In the organic electroluminescent device of the present disclosure, a mixed region of an electron transport compound and a reductive dopant or a mixed region of a hole transport compound and an oxidative dopant can be placed on at least one surface of a pair of electrodes. In this case, the electron transport compound is reduced to anions, so it becomes easier to inject electrons and transfer them from the mixed region to the electroluminescent medium. In addition, the hole transport compound is oxidized to cations, so it becomes easier to inject holes and transfer them from the mixed region to the electroluminescent medium. Preferably, the oxidative dopant includes various Lewis acids and acceptor compounds; and the reductive dopant includes alkali metals, alkali metal compounds, alkaline earth metals, rare earth metals and mixtures thereof. The reductive dopant layer can be used as a charge generation layer to prepare an electroluminescent device having two or more light-emitting layers and emitting white light.

[0082] To form each layer of the organic electroluminescent device of the present disclosure, a dry film-forming method such as vacuum evaporation, sputtering, plasma, and ion plating methods; or a wet film-forming method such as spin coating, dip coating, and flow coating methods may be used.

[0083] When a wet film forming method is used, a thin film can be formed by dissolving or diffusing the material forming each layer in any suitable solvent such as ethanol, chloroform, tetrahydrofuran, dioxane, etc. The solvent may be any solvent in which the material forming each layer can be dissolved or diffused and in which there is no problem of film forming ability.

[0084] Hereinafter, the organic electroluminescent compound of the present invention, the preparation method of the compound, and the light emitting characteristics of an organic electroluminescent device including the compound will be explained in detail with reference to the following examples.

[0085] [Example 1] Preparation of Compound C-13

[0086]

[0087] 1) Preparation of compound 1-1

[0088] After compound A (22g, 74.88mmol), 4-bromo-3-chloroaniline (13g, 62.40mmol), tetrakis(triphenylphosphine)palladium (2.2g, 1.87mmol), sodium carbonate (17g, 156.00mmol), toluene (310mL), EtOH (80mL) and distilled water (80mL) were introduced into the reaction vessel, the mixture was stirred at 120°C for 6 hours. After the reaction was completed, the mixture was washed with distilled water and extracted with ethyl acetate. The obtained organic layer was dried with magnesium sulfate, and the solvent was removed therefrom by a rotary evaporator. The product was purified by column chromatography to obtain compound 1-1 (14g, yield: 61%).

[0089] 2) Preparation of compound 1-2

[0090] After compound 1-1 (14 g, 37.95 mmol) was introduced into a reaction vessel containing acetonitrile (380 mL), p-toluenesulfonic acid monohydrate (22 g, 113.86 mmol) was added at 0°C. After 10 minutes, sodium nitrite (5 g, 75.90 mmol) and potassium iodide (16 g, 94.88 mmol) were dissolved in distilled water (280 mL), and this solution was then slowly added dropwise to the mixture. After the dropwise addition was completed, the mixture was slowly warmed to room temperature and then stirred for another 4 hours. After the reaction was completed, sodium thiosulfate was added thereto to stop the reaction. The mixture was then extracted with ethyl acetate. The resulting organic layer was dried with magnesium sulfate, and the solvent was removed therefrom by a rotary evaporator. The product was purified by column chromatography to obtain compound 1-2 (9.6 g, yield: 53%).

[0091] 3) Preparation of Compound 1-3

[0092] After compound 1-2 (8.5 g, 17.72 mmol), 2-nitrophenylboric acid (4.4 g, 26.85 mmol), tetrakis (triphenylphosphine) palladium (0.6 g, 0.53 mmol), sodium carbonate (4.7 g, 44.30 mmol), tetrahydrofuran (90 mL) and distilled water (22 mL) were introduced into the reaction vessel, the mixture was stirred at 80 ° C for 4 hours. After the reaction was completed, the mixture was washed with distilled water and extracted with ethyl acetate. The obtained organic layer was dried with magnesium sulfate, and the solvent was removed therefrom by a rotary evaporator. The product was purified by column chromatography to obtain compound 1-3 (7.5 g, yield: 89%).

[0093] 4) Preparation of Compound 1-4

[0094] After compound 1-3 (7g, 14.74mmol), palladium acetate (II) (0.4g, 1.47mmol), tricyclohexylphosphine fluoroborate (1.1g, 2.94mmol), cesium carbonate (15g, 44.22mmol) and o-xylene (74mL) were introduced into the reaction vessel, the mixture was stirred under reflux for 4 hours. After the reaction was completed, the mixture was washed with distilled water and extracted with ethyl acetate. The obtained organic layer was dried with magnesium sulfate, and the solvent was removed therefrom by a rotary evaporator. The product was purified by column chromatography to obtain compound 1-4 (6.3g, yield: 91%).

[0095] 5) Preparation of Compound 1-5

[0096] After compound 1-4 (6.3 g, 14.37 mmol), triphenylphosphine (11.3 g, 43.10 mmol) and 1,2-dichlorobenzene (72 mL) were introduced into the reaction vessel, the mixture was stirred at 200 ° C for 8 hours. After completing the reaction, the mixture was distilled under reduced pressure to remove the solvent. The mixture was then washed with distilled water and extracted with ethyl acetate. The resulting organic layer was dried with magnesium sulfate, and the solvent was removed therefrom by a rotary evaporator. The product was purified by column chromatography to obtain compound 1-5 (1.2 g, yield: 21%).

[0097] 6) Preparation of Compound C-13

[0098] After dissolving compound 1-5 (1.2g, 2.95mmol) in the reaction vessel containing dimethyl formaldehyde (15mL), sodium hydride (0.2g, 4.43mmol) is slowly added dropwise in the mixture at 0 ℃.After stirring the mixture for 30 minutes, 2-chloro-4-phenylquinazoline (0.9g, 3.54mmol) is dropwise added thereto.After completing the dropwise addition, the mixture is warmed up to room temperature, and stirred for another 7 hours.After completing the reaction, methanol is added thereto to stop the reaction.Then the mixture is extracted with ethyl acetate. With the gained organic layer dried over magnesium sulfate, and by rotary evaporator, solvent is removed therefrom.

[0099] The product was purified by column chromatography to obtain compound C-13 (0.8 g, yield: 44%).

[0100]

[0101] [Example 2] Preparation of Compound C-6

[0102]

[0103] 1) Preparation of compound C-6

[0104] After compound B (2.5g, 6.15mmol), 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine (2.9g, 7.38mmol), palladium acetate (II) (0.07g, 0.31mmol), 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (0.3g, 0.62mmol), sodium tert-butoxide (1.5g, 15.38mmol) and o-xylene (31mL) were introduced into the reaction vessel, the mixture was stirred under reflux for 10 hours. After the reaction was completed, the mixture was washed with distilled water and extracted with ethyl acetate. The obtained organic layer was dried with magnesium sulfate, and the solvent was removed therefrom by a rotary evaporator. The product was purified by column chromatography to obtain compound C-6 (0.8g, yield: 18%).

[0105] MW UV PL MP C-6 713.84 406nm 453nm 356℃

[0106] [Example 3] Preparation of Compound C-48

[0107]

[0108] 1) Preparation of compound C-48

[0109] After compound B (2g, 4.90mmol), 3-bromo-1-1'-biphenyl (1.7g, 7.30mmol), CuI (0.5g, 15.04mmol), diaminocyclohexane (1.2mL, 9.80mmol), cesium carbonate (3.2g, 9.80mmol) and o-xylene (25mL) were introduced into the reaction vessel, the mixture was stirred for 7 hours under reflux. After the reaction was completed, the mixture was washed with distilled water and extracted with ethyl acetate. The organic layer obtained was dried over magnesium sulfate, and the solvent was removed therefrom by a rotary evaporator. The product was purified by column chromatography to obtain compound C-48 (1.2g, yield: 89%).

[0110] MW UV PL MP C-48 558.67 386nm 457nm 221℃

[0111] [Example 4] Preparation of Compound C-49

[0112]

[0113] 1) Preparation of compound 4-1

[0114] After compound C (30g, 136.36mmol), phenylboronic acid (20g, 163.64mmol), tetrakis (triphenylphosphine) palladium (4.7g, 4.09mmol), potassium carbonate (47.1g, 340.90mmol), toluene (680mL), EtOH (170mL) and distilled water (170mL) were introduced into the reaction vessel, the mixture was stirred for 4 hours at 120°C. After the reaction was completed, the mixture was washed with distilled water and extracted with ethyl acetate. The obtained organic layer was dried with magnesium sulfate, and the solvent was removed therefrom by a rotary evaporator. The product was purified by column chromatography to obtain compound compound 4-1 (28g, yield: 96%).

[0115] 2) Preparation of compound 4-2

[0116] After dissolving compound 4-1 (28 g, 128.91 mmol) and 1-bromo-9H-carbazole (24 g, 97.52 mmol) in dimethyl formaldehyde (600 mL) in a reaction vessel, sodium hydride (6 g, 146.28 mmol, 60% in mineral oil) was added to the mixture at 0°C. The mixture was stirred at room temperature for 3 hours. After the reaction was completed, methanol and distilled water were added thereto. The obtained solid was filtered under reduced pressure, and column chromatography was performed to obtain compound 4-2 (19 g, yield: 46%).

[0117] 3) Preparation of compound 4-3

[0118] After compound 4-2 (19 g, 45.20 mmol), 2-chlorophenylboronic acid (8.5 g, 54.24 mmol), tetrakis (triphenylphosphine) palladium (1.6 g, 4.09 mmol), sodium carbonate (12 g, 113.00 mmol), toluene (230 mL), EtOH (56 mL) and distilled water (56 mL) were introduced into the reaction vessel, the mixture was stirred at 120 ° C for 2 hours. After the reaction was completed, the mixture was washed with distilled water and extracted with ethyl acetate. The obtained organic layer was dried with magnesium sulfate, and the solvent was removed therefrom by a rotary evaporator. The product was purified by column chromatography to obtain compound 4-3 (20 g, yield: 93%).

[0119] 4) Preparation of compound 4-4

[0120] After compound 4-3 (20g, 41.90mmol), palladium acetate (II) (1g, 4.19mmol), tricyclohexylphosphine fluoroborate (3.1g, 8.38mmol), cesium carbonate (41g, 125.70mmol) and o-xylene (210mL) were introduced into the reaction vessel, the mixture was stirred for 3 hours under reflux. After the reaction was completed, the mixture was washed with distilled water and extracted with ethyl acetate. The obtained organic layer was dried with magnesium sulfate, and the solvent was removed therefrom by a rotary evaporator. The product was purified by column chromatography to obtain compound 4-4 (14g, yield: 78%).

[0121] 5) Preparation of compound 4-5

[0122] After compound 4-4 (14 g, 32.75 mol), triphenylphosphine (26 g, 98.25 mmol) and 1,2-dichlorobenzene (165 mL) were introduced into the reaction vessel, the mixture was stirred at 200 ° C for 8 hours. After completing the reaction, the mixture was distilled under reduced pressure to remove the solvent, then the mixture was washed with distilled water and extracted with ethyl acetate. The resulting organic layer was dried with magnesium sulfate, and the solvent was removed therefrom by a rotary evaporator. The product was purified by column chromatography to obtain compound 4-5 (10 g, yield: 75%).

[0123] 6) Preparation of Compound C-49

[0124] After compound 4-5 (2 g, 4.90 mmol), 2-chloro-3-phenylquinoxaline (1.8 g, 7.30 mmol), 4-dimethylaminopyridine (0.3 g, 2.45 mmol), potassium carbonate (1.0 g, 7.30 mmol) and dimethylformamide (25 mL) were introduced into a reaction vessel, the mixture was stirred at 150 ° C for 9 hours. After the reaction was completed, methanol was added thereto to stop the reaction. The mixture was then extracted with ethyl acetate. The resulting organic layer was dried over magnesium sulfate, and the solvent was removed therefrom by a rotary evaporator. The product was purified by column chromatography to obtain compound C-49 (0.9 g, yield: 30%).

[0125] MW UV PL MP C-49 610.70 401nm 513nm 231℃

[0126] [Example 5] Preparation of Compound C-50

[0127]

[0128] 1) Preparation of compound 5-1

[0129] After compound D (5.0 g, 10.95 mmol) was dissolved in dimethyl formaldehyde (55 mL) of a reaction vessel, sodium hydride (0.7 g, 16.43 mmol) was slowly added dropwise to the mixture at 0 ° C. After the mixture was stirred for 30 minutes, 2,3-dichloroquinoxaline (3.3 g, 16.43 mmol) was added dropwise thereto. After the dropwise addition was completed, the mixture was warmed to room temperature and stirred for another 4 hours. After the reaction was completed, methanol was added thereto to stop the reaction. The mixture was then extracted with ethyl acetate. The resulting organic layer was dried with magnesium sulfate, and the solvent was removed therefrom by a rotary evaporator. The product was purified by column chromatography to obtain compound 5-1 (5.1 g, yield: 75%).

[0130] 2) Preparation of Compound C-50

[0131] After compound 5-1 (5.1 g, 8.24 mmol), phenylboronic acid (1.2 g, 9.89 mmol), tetrakis (triphenylphosphine) palladium (0.3 g, 0.25 mmol), sodium carbonate (2.2 g, 20.60 mmol), toluene (42 mL), EtOH (10 mL) and distilled water (10 mL) were introduced into the reaction vessel, the mixture was stirred at 120 ° C for 4 hours. After the reaction was completed, the mixture was washed with distilled water and extracted with ethyl acetate. The organic layer was dried over magnesium sulfate and the solvent was removed therefrom by a rotary evaporator. The product was purified by column chromatography to obtain compound C-50 (2.5 g, yield: 46%).

[0132] MW UV PL MP C-50 660.78 406nm 519nm 280℃

[0133] [Example 6] Preparation of Compound C-51

[0134]

[0135] 1) Preparation of compound C-51

[0136] After compound D (3.0g, 6.57mmol) was dissolved in dimethyl formaldehyde (33mL) in the reaction vessel, sodium hydride (0.4g, 9.86mmol) was slowly added dropwise to the mixture at 0°C. After stirring the mixture for 30 minutes, 2-chloro-4-phenylquinazoline (1.9g, 7.89mmol) was added dropwise thereto. After completing the dropwise addition, the mixture was warmed to room temperature and stirred for another 6 hours. After completing the reaction, methanol was added thereto to stop the reaction. The mixture was then extracted with ethyl acetate. The obtained organic layer was dried over magnesium sulfate, and the solvent was removed therefrom by a rotary evaporator. The product was purified by column chromatography to obtain compound C-51 (1.4g, yield: 33%).

[0137] MW UV PL MP C-51 660.78 416nm 527nm 308℃

[0138] [Device Example 1] OLED produced by the organic electroluminescent compound disclosed herein

[0139] OLED was manufactured by using the organic electroluminescent material of the present invention as follows. A transparent electrode indium tin oxide (ITO) film (10Ω / sq) on a glass substrate of an organic electroluminescent device (OLED) (Geomatec) was ultrasonically cleaned using acetone, ethanol, and distilled water in sequence, and then stored in isopropanol. The ITO substrate was then mounted on a substrate holder of a vacuum vapor deposition apparatus. Compound HI-1 was introduced into a chamber of the vacuum vapor deposition apparatus, and the pressure in the chamber of the apparatus was then controlled to 10 -6Toler. Thereafter, a current is applied to the chamber to evaporate compound HI-1, thereby forming a first hole injection layer having a thickness of 80nm on the ITO substrate. Compound HI-2 is then introduced into another chamber of a vacuum vapor deposition apparatus, and evaporated by applying a current to the chamber, thereby forming a second hole injection layer having a thickness of 5nm on the first hole injection layer. Compound HT-1 is introduced into a chamber of a vacuum vapor deposition apparatus, and evaporated by applying a current to the chamber, thereby forming a first hole transport layer having a thickness of 10nm on the second hole injection layer. Then, compound HT-3 is introduced into another chamber of a vacuum vapor deposition apparatus, and evaporated by applying a current to the chamber, thereby forming a second hole transport layer having a thickness of 60nm on the first hole transport layer. After forming the hole injection layer and the hole transport layer, a light-emitting layer is then deposited thereon. Compound C-13 is introduced into a chamber of a vacuum vapor deposition apparatus as a host material, and compound D-71 is introduced into another chamber. Then, the two compounds were evaporated at different rates so that the dopant was deposited at a doping amount of 3 wt % based on the total amount of the host and the dopant to form a 40 nm thick light-emitting layer on the hole transport layer. Then, the compounds ET-1 and EI-1 were introduced into two other chambers of the vacuum vapor deposition equipment, and evaporated at the same rate of 1:1, thereby forming a 30 nm thick electron transport layer on the light-emitting layer. After depositing the compound EI-1 as a 2 nm thick electron injection layer on the electron transport layer, an Al cathode with a thickness of 80 nm was then deposited on the electron injection layer by another vacuum vapor deposition equipment to manufacture an OLED.

[0140]

[0141] The fabricated OLED exhibited red light emission with a luminous efficiency of 24.1 cd / A at a voltage of 4.2 V and a luminous efficiency of 1,000 cd / m 2 brightness.

[0142] [Device Examples 2, 3, 4, 5] OLEDs manufactured using the organic electroluminescent compounds disclosed herein

[0143] An OLED was manufactured in the same manner as in Device Example 1, except that the compounds shown in the following Table 1 were used as a host material of the light-emitting layer.

[0144]

[0145]

[0146]

[0147] [Comparative Device Example] OLED manufactured by conventional organic electroluminescent compounds

[0148] An OLED was manufactured in the same manner as in Device Example, except that Compound B was used as a host material for the light-emitting layer.

[0149]

[0150] Compound B

[0151] The fabricated OLED exhibited red light emission with a luminous efficiency of 3.3 cd / A at a voltage of 8.2 V and a luminous efficiency of 1,000 cd / m 2 brightness.

[0152] As confirmed by the Device Examples and Comparative Device Examples, the organic electroluminescent compound of the present disclosure has better luminous efficiency than conventional compounds and particularly shows excellent current and power efficiency.

Claims

1. An organic electroluminescent compound represented by the following formula 4 or 5: In formula 4 or 5, R1 to R4 each independently represent hydrogen or deuterium; R5 represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, or may be bonded to an adjacent substituent to form a substituted or unsubstituted (C3-C30) monocyclic or polycyclic alicyclic ring or aromatic ring, the carbon atoms of which may be replaced by at least one heteroatom selected from nitrogen, oxygen and sulfur; and Ar1 represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted triazine group, a substituted or unsubstituted quinoxalinyl group, and a substituted or unsubstituted quinazolinyl group; The substituents of the substituted phenyl, substituted triazinyl, substituted quinoxalinyl or substituted quinazolinyl are each independently selected from the group consisting of deuterium, phenyl, biphenyl, terphenyl and naphthyl; a, c, d and e each independently represent an integer of 1 to 4; b represents an integer of 1 to 3; f and g each independently represent an integer of 1 or 2; and The heteroaryl group contains at least one heteroatom selected from B, N, O, S, Si and P.

2. The organic electroluminescent compound according to claim 1, wherein in R5, the substituents of the substituted (C1-C30)alkyl, substituted (C6-C30)aryl, substituted (3-30 membered)heteroaryl and substituted (C3-C30)monocyclic or polycyclic alicyclic ring or aromatic ring are each independently selected from the group consisting of deuterium, halogen, cyano, carboxyl, nitro, hydroxyl, (C1-C30)alkyl, halogen (C1-C30) aryl, substituted (3-30 membered)heteroaryl and substituted (C3-C30)monocyclic or polycyclic alicyclic ring or aromatic ring. -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, (5-30 membered)heteroaryl substituted or unsubstituted by (C6-C30)aryl, (5-30 membered) heteroaryl-substituted or unsubstituted (C6-C30)aryl, 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)arylborylcarbonyl, di(C1-C30)alkylborylcarbonyl, (C1-C30)alkyl(C6-C30)arylborylcarbonyl, (C6-C30)aryl(C1-C30)alkyl and (C1-C30)alkyl(C6-C30)aryl.

3. The organic electroluminescent compound according to claim 1, wherein the compound represented by Formula 4 or 5 is selected from the group consisting of: An organic electroluminescent device comprising the organic electroluminescent compound according to claim 1 .

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