Organic electroluminescent compound and organic electroluminescent device comprising the same

Abstract

The present application relates to an organic electroluminescent compound and an organic electroluminescent device comprising the compound. The present invention relates to an organic electroluminescent compound and an organic electroluminescent device comprising the compound. By using the organic electroluminescent compound of the present invention, an organic electroluminescent device showing excellent luminescence efficiency (e.g., current efficiency) can be provided.

Description

[0001] This application is a divisional application of the invention patent application with international application number PCT / KR2014 / 011968, international application date December 5, 2014, application number 201480063491.2 entering the Chinese national phase, and invention name “Organic electroluminescent compounds and organic electroluminescent devices comprising the same”. Technical Field

[0002] The present invention relates to an organic electroluminescent compound and an organic electroluminescent device comprising the compound. Background Art

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

[0004] The most important factor determining the luminous efficiency in an organic EL device is the luminescent material. To date, fluorescent materials have been widely used as luminescent materials. However, in view of the electroluminescent mechanism, phosphorescent luminescent materials have been widely studied because phosphorescent materials theoretically enhance the luminous efficiency by four (4) times compared to fluorescent materials. Iridium (III) complexes have been widely known as phosphorescent materials, including bis (2- (2'-benzothienyl) -pyridinyl -N, C-3') iridium (acetylacetonate) ((acac) Ir (btp) 2), tris (2-phenylpyridine) iridium (Ir (ppy) 3) and bis (4,6-difluorophenylpyridinyl -N, C2) picolinate iridium (Firpic) as materials emitting red light, green light and blue light, respectively.

[0005] At present, 4,4'-N,N'-dicarbazole-biphenyl (CBP) is the most widely known host material for phosphorescent materials. Recently, Pioneer (Japan) et al. developed a high-efficiency organic EL device using bathocuproine (BCP) and aluminum (III) bis (2-methyl-8-quinolinate) (4-phenylphenolate) (BAlq) as host materials, which are called hole blocking materials.

[0006] Although these materials provide good luminescent characteristics, they have the following disadvantages: (1) Due to their low glass transition temperature and poor thermal stability, they may degrade in a vacuum during a high temperature deposition process, which results in a poor service life. (2) The power efficiency of an organic EL device is given by [(π / voltage)×current efficiency], and the power efficiency is inversely proportional to the voltage. Although an organic EL device containing a phosphorescent host material provides a higher current efficiency (cd / A) than an organic EL device containing a fluorescent material, a significantly high driving voltage is required. Therefore, there is no advantage in terms of power efficiency (lm / W). (3) In addition, the operating life of an organic EL device is short, and there is still a need to improve the luminous efficiency.

[0007] To improve efficiency and stability, an organic EL device may be manufactured with a multilayer structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, etc. In the structure, a compound used for the hole transport layer is essential for enhancing device characteristics such as efficiency of transporting holes to the light emitting layer, light emitting efficiency, and service life.

[0008] In this regard, 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), and the like are used as hole injection and transport materials for organic EL devices. However, organic EL devices using these materials are problematic in terms of quantum efficiency and service life. This is because, when the organic EL device is driven at a high current, thermal stress is generated between the anode and the hole injection layer. The thermal stress significantly shortens the service life of the device. In addition, since the organic material used for the hole injection layer has an extremely high hole mobility, the hole-electron charge balance may be broken and the quantum yield (cd / A) may be reduced.

[0009] Korean Patent Application Publication No. 10-2012-0029446, WO 2013-065589, and WO 2007-119800 disclose amine derivatives having a benzofluorene-based substituent as a compound for an organic EL device. However, the benzofluorene-based substituent of the reference is a benzo[a]fluorene- or benzo[c]fluorene-based substituent. The reference does not specifically disclose an amine derivative having a benzo[b]fluorene-based substituent. Summary of the invention

[0010] Problems to be solved

[0011] An object of the present invention is to provide an organic electroluminescent compound showing luminous efficiency (eg, current efficiency), and an organic electroluminescent device comprising the compound.

[0012] Solution to the problem

[0013] The present inventors have found that the above object can be achieved by an organic electroluminescent compound represented by Formula 1 below.

[0014]

[0015] in

[0016] Ar1 to Ar4 each independently represent a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (5- to 30-membered) heteroaryl group; and Ar1 and Ar2 may be fused to each other to form a ring;

[0017] Ar5 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;

[0018] L1 represents a single bond, a substituted or unsubstituted (C6-C30)arylene group, or a substituted or unsubstituted (5- to 30-membered)heteroarylene group;

[0019] L2 represents a substituted or unsubstituted (C1-C30)alkylene group, a substituted or unsubstituted (C6-C30)arylene group, or a substituted or unsubstituted (5- to 30-membered)heteroarylene group;

[0020] R1 and R2 each independently represent 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 (3-7 membered)heterocycloalkyl, substituted or unsubstituted (C6-C30)aryl(C1-C30)alkyl, -N(R 11 )(R 12 )、-Si(R 13 )(R 14 )(R 15 )、-S(R 16 )、-O(R 17 ), cyano, nitro or hydroxyl; or may be linked to adjacent substituents to form a (3 to 30 membered) 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;

[0021] R 11 to R 17Each independently represents 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 (3-7 membered) heterocycloalkyl, or substituted or unsubstituted (C3-C30) cycloalkyl; or may be linked with adjacent substituents to form a (3-30 membered) 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;

[0022] n and m each independently represent 0 or 1, with the restriction that n and m cannot be 0 at the same time;

[0023] a represents an integer from 1 to 3; wherein a is an integer of 2 or greater, and each R1 may be the same or different;

[0024] b represents an integer from 1 to 6; wherein b is an integer of 2 or greater, and each R2 may be the same or different;

[0025] The (ene)heteroaryl group contains at least one heteroatom selected from B, N, O, S, P(═O), Si and P; and

[0026] The heterocycloalkyl group contains at least one heteroatom selected from O, S and N.

[0027] Advantageous Effects of the Invention

[0028] The organic electroluminescent compound of the present invention can provide an organic electroluminescent device showing excellent luminous efficiency (eg, current efficiency). DETAILED DESCRIPTION

[0029] Hereinafter, the present invention will be described in detail. However, the following description is intended to explain the present invention and is not intended to limit the scope of the present invention in any way.

[0030] The present invention provides an organic electroluminescent compound of the above formula 1, an organic electroluminescent material comprising the organic electroluminescent compound, and an organic electroluminescent device comprising the organic electroluminescent compound.

[0031] Details of the organic electroluminescent compound of Formula 1 are as follows.

[0032] Herein, "alkyl" includes methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, etc. "Alkenyl" includes vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 2-methylbut-2-enyl, etc. "Alkynyl" includes ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methylpent-2-ynyl, etc. "Cycloalkyl" includes cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc. "(3 to 7 membered) heterocycloalkyl" indicates a cycloalkyl group having 3 to 7 ring backbone atoms, which includes at least one heteroatom selected from the following: B, N, O, S, P(=O), Si and P, preferably O, S and N, and includes tetrahydrofuran, pyrrolidine, thiolane, tetrahydropyran, etc. In addition, "(y)aryl" means a single ring or a condensed ring derived from an aromatic hydrocarbon, and includes phenyl, biphenyl, terphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, phenylphenanthryl, anthracenyl, indenyl, triphenylene, pyrene, naphthacene, peryl, chrysene, condensed tetraphenyl, fluoranthenyl, and the like. The “(5- to 30-membered) (sub)heteroaryl” refers to an aryl group having 5 to 30 ring backbone atoms and including at least one, preferably 1 to 4, heteroatoms selected from the group consisting of B, N, O, S, P(═O), 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 connecting at least one heteroaryl or aryl group to a heteroaryl group via a single bond; and includes monocyclic heteroaryl groups such as furanyl, thienyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl , tetrazolyl, furazolyl, pyridyl, bipyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and the like, and condensed ring heteroaryl, such as benzofuranyl, benzothienyl, isobenzofuranyl, dibenzofuranyl, dibenzothienyl, naphthofuranyl, naphthothienyl, benzonaphthofuranyl, benzonaphthothienyl, benzimidazolyl, benzothiazolyl, benzisothiazolyl, benzisoxazolyl, benzoxazolyl, isoindolyl, indolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, phenoxazinyl, phenidinyl, benzodioxolyl, and the like. In addition, "halogen" includes F, Cl, Br and I.

[0033] Herein, the term "substituted" in the expression "substituted or unsubstituted" means that a hydrogen atom in a functional group is replaced by another atom or group, i.e., a substituent. Ar1 to Ar5, L1, L2, R1, R2, and R 11 to R 17The substituents of the substituted (ene) alkyl, substituted (ene) aryl, substituted (ene) heteroaryl, substituted cycloalkyl, substituted heterocycloalkyl and substituted arylalkyl are each independently at least one selected from the group consisting of: deuterium; halogen; unsubstituted or halogen-substituted (C1-C30) alkyl; (C1-C30) alkoxy; (C6-C30) aryl; unsubstituted or (C6-C30) aryl-substituted (3-30 membered) heteroaryl; (C3-C30) cycloalkyl; (3-7 membered) heterocycloalkyl; tri(C1-C30) alkylsilanyl; tri(C6-C30) arylsilanyl; di(C1-C30) alkyl(C6-C30) arylsilanyl; (C1-C30) alkyldi(C6-C30) arylsilanyl; (C2-C30) alkenyl; (C 2-C30)alkynyl; cyano; di(C1-C30)alkylamino; di(C6-C30)arylamino which is unsubstituted or substituted by (C1-C30)alkyl; (C1-C30)alkyl(C6-C30)arylamino; di(C6-C30)arylboryl; di(C1-C30)alkylboryl; (C1-C30)alkyl(C6-C30)arylboryl; (C6-C30)alkyl(C6-C30)arylboryl; )aryl(C1-C30)alkyl; (C1-C30)alkyl(C6-C30)aryl; carboxyl; nitro; and hydroxyl; and are preferably each independently at least one selected from the group consisting of: (C1-C30)alkyl; (C6-C21)aryl; (5 to 21 membered)heteroaryl which is unsubstituted or substituted with (C6-C12)aryl; and di(C6-C21)arylamino.

[0034] According to one aspect of the present invention, the compound of formula 1 is represented by any one of the following formulas 2 to 4, and preferably the following formula 2 or 3:

[0035]

[0036] wherein Ar1 to Ar5, L1, L2, R1, R2, a and b are as defined above in Formula 1.

[0037] In Formulae 1 to 4, Ar1 to Ar4 each independently represent a substituted or unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted (5- to 30-membered) heteroaryl group, and Ar1 and Ar2 may be fused to each other to form a ring. Preferably, Ar1 to Ar4 each independently represent a substituted or unsubstituted (C6-C21)aryl group, or a substituted or unsubstituted (5- to 21-membered) heteroaryl group, and Ar1 and Ar2 may be fused to each other to form a ring; and more preferably, represent a substituted or unsubstituted (C6-C21)aryl group, the substituent of the (C6-C21)aryl group may be at least one selected from the group consisting of: a (C1-C30)alkyl group, an unsubstituted or (C1-C10)alkyl-substituted (C6-C21)aryl group, and an unsubstituted or (C6-C12)aryl-substituted (5- to 21-membered) heteroaryl group, and Ar1 and Ar2 may be fused to each other to form a ring. Specifically, Ar1 to Ar4 may each independently represent a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group or a benzofluorenyl group, and Ar1 and Ar2 may be fused to each other to form a ring. Specifically, the substituents of Ar1 to Ar4 may be at least one selected from the group consisting of: (C1-C4) alkyl, phenyl, naphthyl, fluorenyl, 9,9-dimethyl-9H-fluorenyl, pyridyl, pyrimidyl, quinolyl, isoquinolyl, quinazolyl, quinoxalinyl, 9-phenylcarbazolyl, dibenzothiophenyl and dibenzofuranyl.

[0038] Specifically, the ring formed by Ar1 and Ar2 can be represented by the following formula 5:

[0039]

[0040] wherein R3 and R4 each independently represent hydrogen, (C1-C30)alkyl, (C6-C30)aryl, or (3- to 30-membered) heteroaryl which is unsubstituted or substituted with (C6-C30)aryl; and * represents the site of attachment to L1.

[0041] Specifically, one of R3 and R4 represents hydrogen, and the other may be selected from the group consisting of: (C1-C4) alkyl; phenyl; biphenyl; naphthyl; unsubstituted or substituted carbazolyl with phenyl, biphenyl or naphthyl; unsubstituted or substituted dibenzothienyl with phenyl, biphenyl or naphthyl; and unsubstituted or substituted dibenzofuranyl with phenyl, biphenyl or naphthyl.

[0042] Ar5 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. Preferably, Ar5 represents a substituted or unsubstituted (C1-C20) alkyl group, a substituted or unsubstituted (C6-C21) aryl group, or a substituted or unsubstituted (5- to 21-membered) heteroaryl group. More preferably, Ar5 represents unsubstituted (C1-C10)alkyl; unsubstituted or substituted (C1-C10)alkyl, (C6-C21)aryl, (6- to 21-membered)heteroaryl which is unsubstituted or substituted with (C6-C13)aryl, or (C6-C18)arylamino-substituted (C6-C18)aryl; or (6- to 21-membered)heteroaryl which is unsubstituted or substituted with (C1-C10)alkyl or (C6-C18)aryl and contains a heteroatom selected from N, O and S. Specifically, Ar5 represents (C1-C4) alkyl; phenyl, biphenyl, naphthyl, terphenyl, phenanthryl, anthracenyl or fluorenyl, which is unsubstituted or substituted with (C1-C4) alkyl, phenyl, carbazolyl, diphenylpyrimidinyl, diphenyltriazine, phenylbenzimidazolyl, diphenylamino, (phenyl)(biphenyl)amino, di(biphenyl)amino or (phenyl)(naphthyl)amino; or carbazolyl, benzocarbazolyl, dibenzothiophenyl, benzonaphthothiophenyl, dibenzofuranyl or benzonaphthofuranyl, which is unsubstituted or substituted with phenyl.

[0043] L1 represents a single bond, a substituted or unsubstituted (C6-C30)arylene group, or a substituted or unsubstituted (5- to 30-membered)heteroarylene group. Preferably, L1 represents a single bond, a substituted or unsubstituted (C6-C21)arylene group, or a substituted or unsubstituted (5- to 21-membered)heteroarylene group. More preferably, L1 represents a single bond; an unsubstituted or (C1-C10)alkyl-substituted (C6-C18)arylene group; or an unsubstituted or (C1-C10)alkyl-substituted (5- to 18-membered)heteroarylene group containing nitrogen as a heteroatom. Specifically, L1 represents a single bond, a phenyl group, or a pyrimidinyl group.

[0044] L2 represents a substituted or unsubstituted (C1-C30)alkylene group, a substituted or unsubstituted (C6-C30)arylene group, or a substituted or unsubstituted (5- to 30-membered)heteroarylene group. Preferably, L2 represents a substituted or unsubstituted (C1-C20)alkylene group, a substituted or unsubstituted (C6-C21)arylene group, or a substituted or unsubstituted (5- to 21-membered)heteroarylene group. More preferably, L2 represents an unsubstituted (C1-C10)alkylene group; an unsubstituted or (C1-C10)alkyl-substituted (C6-C18)arylene group; or an unsubstituted or (C1-C10)alkyl-substituted (6- to 21-membered)heteroarylene group containing oxygen as a heteroatom. Specifically, L2 represents a (C1-C4) alkyl group, a phenyl group, a biphenyl group, a naphthyl group, a fluorenyl group, a 9,9-dimethyl-9H-fluorenyl group or a dibenzofuranyl group.

[0045] R1 and R2 each independently represent 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 (3-7 membered)heterocycloalkyl, substituted or unsubstituted (C6-C30)aryl(C1-C30)alkyl, -N(R 11 )(R 12 )、-Si(R 13 )(R 14 )(R 15 )、-S(R 16 )、-O(R 17 ), cyano, nitro or hydroxyl, or may be linked to adjacent substituents to form a (3 to 30 membered) 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. 11 to R 17 Each independently represents 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 (3-7 membered) heterocycloalkyl, or substituted or unsubstituted (C3-C30) cycloalkyl; or may be connected with adjacent substituents to form a (3-30 membered) 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, R1 and R2 each independently represent hydrogen, substituted or unsubstituted (C1-C20) alkyl, substituted or unsubstituted (C6-C21) aryl, substituted or unsubstituted (5-21 membered) heteroaryl, or -N(R 11 )(R 12 ). Preferably, R 11 and R12 Each independently represents a substituted or unsubstituted (C6-C21)aryl group. More preferably, R1 and R2 each independently represent hydrogen; an unsubstituted (C6-C18)aryl group; an unsubstituted (6 to 18-membered) heteroaryl group containing nitrogen as a heteroatom; or -N(R 11 )(R 12 ). More preferably, R 11 and R 12 Each independently represents an unsubstituted (C6-C18)aryl group. Specifically, R1 and R2 each independently represent hydrogen, phenyl, pyridyl, pyrimidyl, carbazolyl, diphenylamino, (phenyl)(biphenylyl)amino, di(biphenylyl)amino or (phenyl)(naphthyl)amino.

[0046] n and m each independently represent 0 or 1, with the restriction that n and m cannot be 0 at the same time.

[0047] a represents an integer from 1 to 3; wherein a is an integer of 2 or more, and each R1 may be the same or different. Preferably, a represents 1.

[0048] b represents an integer from 1 to 6; wherein b is an integer of 2 or more, and each R2 may be the same or different. Preferably, b represents 1.

[0049] According to one embodiment of the present invention, in Formulae 1 to 4, Ar1 to Ar4 each independently represent a substituted or unsubstituted (C6-C21) aryl group or a substituted or unsubstituted (5-21 membered) heteroaryl group; and Ar1 and Ar2 may be fused to each other to form a ring; Ar5 represents a substituted or unsubstituted (C1-C20) alkyl group, a substituted or unsubstituted (C6-C21) aryl group or a substituted or unsubstituted (5-21 membered) heteroaryl group; L1 represents a single bond, a substituted or unsubstituted (C6 -C21)arylene or substituted or unsubstituted (5- to 21-membered)heteroarylene; L2 represents a substituted or unsubstituted (C1-C20)alkylene, a substituted or unsubstituted (C6-C21)arylene or a substituted or unsubstituted (5- to 21-membered)heteroarylene; R1 to R2 each independently represent hydrogen, a substituted or unsubstituted (C1-C20)alkyl, a substituted or unsubstituted (C6-C21)aryl, a substituted or unsubstituted (5- to 21-membered)heteroaryl or -N(R 11 )(R 12 );R 11 and R 12Each independently represents a substituted or unsubstituted (C6-C21)aryl group; n and m each independently represent 0 or 1, with the restriction that n and m cannot be 0 at the same time; a represents an integer from 1 to 3; wherein a is an integer of 2 or greater, and each R1 may be the same or different; b represents an integer from 1 to 6; wherein b is an integer of 2 or greater, and each R2 may be the same or different; and the (sub)heteroaryl group contains at least one heteroatom selected from N, O and S.

[0050] According to another embodiment of the present invention, in Formulae 1 to 4, Ar1 to Ar4 each independently represent a substituted or unsubstituted (C6-C21)aryl group, the substituent of the (C6-C21)aryl group may be at least one selected from the group consisting of: a (C1-C30)alkyl group, a (C6-C21)aryl group that is unsubstituted or substituted with a (C1-C10)alkyl group, and a (5- to 21-membered)heteroaryl group that is unsubstituted or substituted with a (C6-C12)aryl group, and Ar1 and Ar2 may be fused to each other to form a ring; Ar5 represents an unsubstituted (C1-C10)alkyl group, a (C6-C18)aryl group that is unsubstituted or substituted with a (C1-C10)alkyl group, a (C6-C21)aryl group, a (6- to 21-membered)heteroaryl group that is unsubstituted or substituted with a (C6-C13)aryl group, or a di(C6-C18)arylamino group, or an unsubstituted wherein L1 represents a single bond, an unsubstituted or (C1-C10)alkyl-substituted (C6-C18)arylene group, or an unsubstituted or (C1-C10)alkyl-substituted (C6-C18)arylene group, or an unsubstituted or (C1-C10)alkyl-substituted (C6-C18)arylene group, or an unsubstituted or (C1-C10)alkyl-substituted (6- to 21-membered)heteroarylene group, containing a heteroatom selected from N, O and S; L1 represents a single bond, an unsubstituted or (C1-C10)alkyl-substituted (C6-C18)arylene group, or an unsubstituted or (C1-C10)alkyl-substituted (C6-C18)arylene group, or an unsubstituted or (C1-C10)alkyl-substituted (6- to 21-membered)heteroarylene group containing an oxygen as a heteroatom; R1 and R2 each independently represent hydrogen, an unsubstituted (C6-C18)aryl group, an unsubstituted (6- to 18-membered)heteroaryl group containing a nitrogen as a heteroatom, or -N(R 11 )(R 12 );R 11 and R 12 each independently represents an unsubstituted (C6-C18)aryl group; n and m each independently represent 0 or 1, with the restriction that n and m cannot be 0 at the same time; a represents 1; and b represents 1.

[0051] More specifically, the organic electroluminescent compounds of Formula 1 include (but are not limited to) the following:

[0052]

[0053]

[0054]

[0055]

[0056] The organic electroluminescent compound of the present invention can be prepared by a synthetic method known to those skilled in the art. For example, it can be prepared according to the following reaction scheme 1 or 2.

[0057] [Reaction Scheme 1]

[0058]

[0059] [Reaction Scheme 2]

[0060]

[0061] In addition, the present invention provides an organic electroluminescent material comprising the organic electroluminescent compound of Formula 1 and an organic electroluminescent device comprising the material.

[0062] The material may be composed of the organic electroluminescent compound of the present invention. In addition, in addition to the compound of the present invention, the material may further contain conventional compounds already contained in the organic electroluminescent material. Preferably, the organic electroluminescent material may be a host material or a hole transport material.

[0063] The organic electroluminescent device of the present invention 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 compound of Formula 1.

[0064] 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 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 interlayer, a hole blocking layer, an electron buffer layer, and an electron blocking layer.

[0065] The organic electroluminescent compound of the present invention may be contained in at least one of the light-emitting layer and the hole transport layer. When used in the hole transport layer, the organic electroluminescent compound of the present invention may be contained therein as a hole transport material. When used in the light-emitting layer, the organic electroluminescent compound of the present invention may be contained as a host material.

[0066] When the organic electroluminescent compound of the present invention is included as a hole transport material, the light-emitting layer may include a light-emitting material known in the art, or an organic electroluminescent compound of the present invention other than the compound of the present invention used as a hole transport material. The light-emitting material known in the art may be a host material known in the art, and may further include at least one dopant. The host material known in the art may be a fluorescent or phosphorescent host material known in the art.

[0067] When the organic electroluminescent compound of the present invention is included in the light-emitting layer as a host material (first host material), at least one dopant may be further included, and if necessary, another compound may be included as a second host material. The weight ratio between the first host material and the second host material is in the range of 1:99 to 99:1.

[0068] A compound selected from the group consisting of compounds of the following Formulae 6 to 8 is preferred as a known host material or a second host material due to light emitting efficiency.

[0069] H-(Cz-L4) h -M (6)

[0070] H-(Cz) i -L4-M (7)

[0071]

[0072] Wherein, Cz represents the following structure:

[0073]

[0074] R 21 to R 24 Each independently represents hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, or R 25 R 26 R 27 Si-;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 31 )-or-C(R 32 )(R33 )-, the restriction condition is that Y1 and Y2 do not exist at the same time; R 31 to R 33 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 32 and R 33 may be the same or different; h and i each independently represent an integer from 1 to 3; j, k, o and r each independently represent an integer from 0 to 4; and in the case where h, i, j, k, o or r is an integer of 2 or greater, each of (Cz-L4), each of (Cz), R 21 Each of R 22 Each of R 23 Each of the R 24 Each of can be the same or different.

[0075] Specifically, the host materials represented by Formulas 6 to 8 include the following:

[0076]

[0077]

[0078]

[0079] (TPS represents triphenylsilyl.)

[0080] The dopant is preferably at least one phosphorescent dopant. The phosphorescent dopant material for the organic electroluminescent device of the present invention is not limited, but can be preferably selected from metal complex compounds of iridium (Ir), osmium (Os), copper (Cu) or platinum (Pt), more preferably selected from ortho metal complex compounds of iridium (Ir), osmium (Os), copper (Cu) or platinum (Pt), and even more preferably ortho metal iridium complex compounds.

[0081] The phosphorescent dopant may be preferably selected from the group consisting of compounds represented by Formulae 9 to 11 below.

[0082]

[0083]

[0084] Wherein L is selected from the following structures:

[0085]

[0086] R 100represents hydrogen, substituted or unsubstituted (C1-C30) alkyl or substituted or unsubstituted (C3-C30) cycloalkyl; R 101 to R 109 and R 111 to R 123 each independently represents hydrogen, deuterium, halogen, unsubstituted or halogen-substituted (C1-C30)alkyl, cyano, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C6-C30)aryl or substituted or unsubstituted (C1-C30)alkoxy; or R 106 to R 109 It may be connected with an adjacent substituent to form a substituted or unsubstituted condensed ring, such as substituted or unsubstituted fluorene, substituted or unsubstituted dibenzothiophene or substituted or unsubstituted dibenzofuran; or R 120 to R 123 It may be connected with adjacent substituents to form a substituted or unsubstituted condensed ring, such as a substituted or unsubstituted quinoline; 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 127 It may be connected with an adjacent substituent to form a substituted or unsubstituted condensed ring, such as substituted or unsubstituted fluorene, substituted or unsubstituted dibenzothiophene or substituted or unsubstituted dibenzofuran; R 201 to R 211 each independently represents hydrogen, deuterium, halogen, unsubstituted or halogen-substituted (C1-C30)alkyl, substituted or unsubstituted (C3-C30)cycloalkyl or substituted or unsubstituted (C6-C30)aryl, or R 208 to R 211 It may be connected with an adjacent substituent to form a substituted or unsubstituted fused ring, such as a substituted or unsubstituted fluorene, a substituted or unsubstituted dibenzothiophene, or a substituted or unsubstituted dibenzofuran; o and p each independently represent an integer from 1 to 3; wherein o or p is an integer of 2 or more, and each R 100 may be the same or different; and d represents an integer from 1 to 3.

[0087] Specifically, phosphorescent dopant materials include the following:

[0088]

[0089]

[0090]

[0091]

[0092] According to other aspects of the present invention, a mixture or composition for preparing an organic electroluminescent device is provided. The mixture or composition comprises the compound of the present invention. The mixture or composition may be a mixture or composition for preparing a light-emitting layer or a hole transport layer of an organic electroluminescent device. When the compound of the present invention is included in a mixture or composition for preparing a light-emitting layer of an organic electroluminescent device, the compound of the present invention may be included as a host material. When the compound of the present invention is included as a host material, the mixture or composition may further include a second host material, such as those selected from compounds represented by formulas 6 to 8. When the compound of the present invention is included in a mixture or composition for preparing a hole transport layer of an organic electroluminescent device, the compound of the present invention may be included as a hole transport material.

[0093] The organic electroluminescent device of the present invention may include a first electrode, a second electrode and at least one organic layer disposed between the first and second electrodes, wherein the organic layer may include a light-emitting layer or both a light-emitting layer and a hole transport layer, which may include a mixture or composition for preparing the organic electroluminescent device of the present invention.

[0094] In addition to the compound of Formula 1, the organic electroluminescent device of the present invention may further include at least one compound selected from the group consisting of arylamine-based compounds and styrylarylamine-based compounds.

[0095] In the organic electroluminescent device of the present invention, 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 organic metals 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.

[0096] In addition, the organic electroluminescent device of the present invention can emit white light by further comprising at least one light-emitting layer comprising, in addition to the compound of the present invention, a blue electroluminescent compound, a red electroluminescent compound, or a green electroluminescent compound known in the art.

[0097] In the organic electroluminescent device of the present invention, preferably, at least one layer (hereinafter, "surface layer") may be placed on the inner surface of one or both electrodes, the inner surface 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 located on the anode surface of the electroluminescent intermediate layer, and a metal halide layer or a metal oxide is preferably located on the cathode surface of the electroluminescent intermediate layer. Such surface layers provide 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.

[0098] In the organic electroluminescent device of the present invention, 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 may be placed on at least one surface of a pair of electrodes. In this case, the electron transport compound is reduced to an anion, and thus electrons are easily injected and transported from the mixed region to the electroluminescent medium. In addition, the hole transport compound is oxidized to a cation, and thus holes are easily injected and transported 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 manufacture an electroluminescent device having two or more electroluminescent layers and emitting white light.

[0099] In order to form each layer of the organic electroluminescent device of the present invention, a dry film forming method such as vacuum evaporation, sputtering, plasma and ion plating; or a wet film forming method such as inkjet printing, nozzle printing, slit coating, spin coating, dip coating and flow coating can be used.

[0100] 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 there is no problem in film forming ability.

[0101] Hereinafter, the organic electroluminescent compound, the preparation method of the compound and the luminescent characteristics of the device of the present invention will be specifically explained with reference to the following examples.

[0102] Example 1: Preparation of Compound C-1

[0103]

[0104] Preparation of compound 1-1

[0105] After introducing 6-bromoindanone (50 g, 237 mmol), phthalaldehyde (35 g, 261 mmol) and 600 mL of ethanol into the reaction vessel, the mixture was refluxed for 3 hours. The reaction mixture was cooled to 0° C. The crystalline solid was filtered and washed with cold methanol to obtain compound 1-1 (47 g, 64%).

[0106] Preparation of compound 1-2

[0107] After introducing iodine (13.5 g, 53.2 mmol), hypophosphorous acid (25 mL, 243 mmol, 50% aqueous solution) and 800 mL of acetic acid into the reaction vessel, the mixture was stirred at 100 ° C for 30 minutes. After slowly adding compound 1-1 dropwise, the mixture was stirred overnight. The reaction mixture was cooled to room temperature. The crystalline solid was filtered and washed with cold methanol to obtain compound 1-2 (41.5 g, 92%).

[0108] Preparation of Compound 1-3

[0109] After introducing compound 1-2 (39 g, 132 mmol), potassium hydroxide (37 g, 660 mmol), potassium iodide (2.2 g, 13.3 mmol), benzyltriethylammonium chloride (1.5 g, 6.6 mmol), 700 mL of distilled water and 700 mL of dimethyl sulfoxide into the reaction vessel, the mixture was stirred at room temperature for 15 minutes. After adding iodomethane (37 g, 330 mmol), the mixture was stirred at room temperature overnight. The reaction mixture was diluted with ethyl acetate and washed with distilled water. The extracted organic layer was dried with magnesium sulfate, and the solvent was removed from it by a rotary evaporator. The product was purified by column chromatography to obtain compound 1-3 (33 g, 77%).

[0110] Preparation of Compound C-1

[0111] Compound 1-3 (10 g, 31 mmol), diphenyl-4-ylamine (9.9 g, 31 mmol), palladium acetate (II) (0.25 g, 1.24 mmol), tri-tert-butylphosphine (1 mL, 3.1 mmol 50% xylene solution), sodium tert-butoxide (4.5 g, 46.5 mmol) and 150 mL o-xylene were introduced into the reaction vessel and the mixture was refluxed for 1 hour. After cooling to room temperature, the reaction mixture was diluted with ethyl acetate, washed with water several times, dried over anhydrous magnesium sulfate, distilled under reduced pressure and purified by column chromatography to obtain compound C-1 (9.6 g, 55%). The physical properties of compound C-1 are shown in Table 1 below.

[0112] Example 2: Preparation of Compound C-43

[0113]

[0114] Preparation of compound 2-1

[0115] Compound 2-1 was prepared in the same manner as Compounds 1-1 to 1-3 in Example 1, except that 5-bromoindanone was used instead of 6-bromoindanone.

[0116] Preparation of Compound C-43

[0117] Compound 2-1 (10 g, 31 mmol), diphenyl-4-ylamine (9.9 g, 31 mmol), palladium acetate (II) (0.25 g, 1.24 mmol), tri-tert-butylphosphine (1 mL, 3.1 mmol 50% xylene solution), sodium tert-butoxide (4.5 g, 46.5 mmol) and 150 mL o-xylene were introduced into the reaction vessel and the mixture was refluxed for 1 hour. After cooling to room temperature, the reaction mixture was diluted with ethyl acetate, washed with water several times, dried over anhydrous magnesium sulfate, distilled under reduced pressure and purified by column chromatography to obtain compound C-43 (10.8 g, 62%). The physical properties of compound C-43 are shown in Table 1 below.

[0118] Example 3: Preparation of Compound H-71

[0119]

[0120] Preparation of compound 3-1

[0121] After introducing 11H-benzo [b] fluorene-11-one (41.5 g, 181 mmol) and 550 mL of tetrahydrofuran into the reaction vessel, the reaction mixture was cooled to 0 ° C, and then phenylmagnesium bromide (78 mL, 235 mmol, 3 M ether solution) was slowly added dropwise thereto. The reaction mixture was stirred at room temperature for 1 hour. After adding an aqueous solution of ammonium chloride to the reaction mixture to terminate the reaction, the mixture was diluted with ethyl acetate, washed with water, dried over anhydrous magnesium sulfate, distilled under reduced pressure and purified by column chromatography to obtain compound 3-1 (56 g, 99%).

[0122] Preparation of compound 3-2

[0123] After introducing compound 3-1 (28 g, 90.3 mmol), 4-bromotriphenylamine (88 g, 271 mmol) and dichloromethane (MC) (600 mL) into the reaction vessel, the mixture was subjected to a nitrogen atmosphere. 3 mL of Eaton's reagent was slowly added dropwise to the mixture. The mixture was stirred at room temperature for 2 hours. After adding distilled water to terminate the reaction, the mixture was extracted with dichloromethane. The extracted organic layer was dried with magnesium sulfate, and the solvent was removed from it by a rotary evaporator. The product was purified by column chromatography to obtain compound 3-2 (38.9 g, 70%).

[0124] Preparation of Compound C-71

[0125] Compound 3-2 (10 g, 16.27 mmol), 2-naphthylboronic acid (3.4 g, 19.5 mmol), tetrakis (triphenylphosphine) palladium (0.7 g, 0.65 mmol), potassium carbonate (5.6 g, 40.7 mmol), 60 mL toluene and 20 mL ethanol were introduced into the reaction vessel, and 20 mL distilled water was added to the mixture. The mixture was stirred at 120 ° C for 3 hours. After the reaction was completed, the mixture was washed with distilled water and extracted with ethyl acetate. The extracted organic layer was dried with magnesium sulfate, and the solvent was removed from it by a rotary evaporator. The product was purified by column chromatography to obtain compound C-71 (7.6 g, 71%). The physical properties of compound C-71 are shown in Table 1 below.

[0126] Example 4: Preparation of Compound C-89

[0127]

[0128] Preparation of Compound C-89

[0129] Into the reaction vessel, compound 1-3 (5 g, 15.4 mmol), 9-phenyl-9H, 9'H-3,3'-dicarbazole (6.6 g, 16.2 mmol), copper iodide (1.47 g, 7.73 mmol), diaminocyclohexane (3.7 mL, 30.9 mmol), potassium phosphate (9.85 g, 46.4 mmol) and 100 mL of o-xylene were introduced, and the mixture was refluxed for 2 hours. After cooling to room temperature, the mixture was diluted with ethyl acetate, washed with water several times, dried with anhydrous magnesium sulfate, distilled under reduced pressure and purified by column chromatography to obtain compound C-89 (4.8 g, 47%). The physical properties of compound C-89 are shown in Table 1 below.

[0130] Example 5: Preparation of Compound C-125

[0131]

[0132] Preparation of compound 5-1

[0133] After introducing dibenzofuran (21g, 127mmol) and 330mL tetrahydrofuran into the reaction vessel, the mixture was subjected to a nitrogen atmosphere and cooled to -78°C. After slowly adding n-butyl lithium (50mL, 2.5M, 115mmol) dropwise, the mixture was stirred for 2 hours at -78°C. After slowly adding 11H-benzo [B] fluorene-11-one (26g, 115mmol) dissolved in 330mL tetrahydrofuran dropwise, the mixture was slowly warmed to room temperature and stirred overnight. After aqueous ammonium chloride solution was added to the reaction mixture to terminate the reaction, the mixture was extracted with dichloromethane (MC). The extracted organic layer was dried with magnesium sulfate, and the solvent was removed from it by a rotary evaporator. The product was purified by column chromatography to obtain compound 5-1 (44g, 96%).

[0134] Preparation of compound 5-2

[0135] After introducing compound 5-1 (44g, 110mmol), 4-bromotriphenylamine (89g, 276mmol) and 550mL MC into the reaction vessel, the mixture was cooled to 0°C. After adding Eaton's reagent (2.4mL, 2.2mmol), the mixture was warmed to room temperature and then stirred for 3 hours. After aqueous ammonium chloride solution was added to the reaction mixture to terminate the reaction, the mixture was extracted with MC. The extracted organic layer was dried with magnesium sulfate, and the solvent was removed from it by a rotary evaporator. The product was purified by column chromatography to obtain compound 5-2 (55g, 71%).

[0136] Preparation of Compound C-125

[0137] After introducing compound 5-2 (10 g, 14.1 mmol), 2-naphthylboronic acid (2.6 g, 15.6 mmol), tetrakis (triphenylphosphine) palladium (0.8 g, 0.71 mmol), potassium carbonate (4.7 g, 34.1 mmol), 70 mL of toluene and 17 mL of ethanol into the reaction vessel, 17 mL of distilled water was added to the mixture. The mixture was stirred at 120 ° C for 3 hours. After the reaction was completed, the mixture was washed with distilled water and extracted with MC. The extracted organic layer was dried with magnesium sulfate, and the solvent was removed from it by a rotary evaporator. The product was purified by column chromatography to obtain compound C-125 (8.4 g, 80%). The physical properties of compound C-125 are shown in Table 1 below.

[0138]

Table 1

[0139]

[0140]

[0141] [Device Example 1] OLED using the compound of the present invention

[0142] Using the material of the present invention, an OLED is manufactured as follows. A transparent electrode indium tin oxide (ITO) film (10Ω / sq) on a glass substrate of an organic light emitting diode (OLED) (Geomatec) is ultrasonically cleaned using acetone and isopropanol in sequence, and then stored in isopropanol. The ITO substrate is then mounted on a substrate holder of a vacuum vapor deposition apparatus. N1,N1'-([1,1'-biphenyl]-4,4'-diyl)bis(N1-(naphthalene-1-yl)-N4,N4-diphenylbenzene-1,4-diamine) is introduced into a unit of the vacuum vapor deposition apparatus, and then the pressure in the chamber of the apparatus is controlled to 10E. -6Toler. Thereafter, a current is applied to the unit to evaporate the above-mentioned introduced material, thereby forming a hole injection layer with a thickness of 60nm on the ITO substrate. Compound C-1 is then introduced into another unit of the vacuum vapor deposition device, and evaporated by applying a current to the unit, thereby forming a hole transport layer with a thickness of 20nm on the hole injection layer. Thereafter, compound H-1 as shown in Table 2 below is introduced into a unit of a vacuum vapor deposition device as a host material, and compound D-1 is introduced into another unit as a dopant. The two materials are evaporated at different rates so that the dopant is deposited at a doping amount of 15% by weight based on the total amount of the host and the dopant, and a light-emitting layer with a thickness of 30nm is formed on the hole transport layer. Then 2-(4-(9,10-di(naphthalene-2-yl)anthracene-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole is introduced into one unit, and quinolyl lithium is introduced into another unit. The two materials were evaporated at the same ratio so that they were deposited at a doping amount of 50 wt % to form an electron transport layer with a thickness of 30 nm on the light emitting layer. After quinolyl lithium was deposited on the electron transport layer to form an electron injection layer with a thickness of 2 nm, an Al cathode with a thickness of 150 nm was then deposited on the electron injection layer by another vacuum vapor deposition device. Thus, an OLED was manufactured. All materials used to manufacture OLEDs were prepared by -6 The OLED display brightness is 1,500cd / m 2 And the current density is 3.5mA / cm 2 Green light emission.

[0143] [Device Example 2] OLED using the compound of the present invention

[0144] An OLED was manufactured in the same manner as in Device Example 1, except that Compound C-71 was used to form a hole transport layer, and Compounds H-2 and H-3 shown in Table 2 below were used as hosts. The manufactured OLED showed a luminance of 700 cd / m 2 And the current density is 14.0mA / cm 2 of blue light emission.

[0145] [Device Example 3] OLED using the compound of the present invention

[0146] An OLED was manufactured in the same manner as in Device Example 1, except that Compound C-89 was used to form a hole transport layer having a thickness of 20 nm. The manufactured OLED exhibited a luminance of 900 cd / m 2 And the current density is 1.9mA / cm 2 Green light emission.

[0147] [Device Example 4] OLED using the compound of the present invention

[0148] An OLED was manufactured in the same manner as in Device Example 1, except that Compound C-125 was used to form a hole transport layer, and Compounds H-2 and H-3 were used as hosts. The manufactured OLED showed a luminance of 1,200 cd / m 2 And the current density is 25.0mA / cm 2 of blue light emission.

[0149] [Comparative Device Example 1] OLED using conventional compounds

[0150] An OLED was manufactured in the same manner as in Device Example 1, except that a hole transport layer having a thickness of 20 nm was formed using Compound T-1 as shown in Table 2 below. The manufactured OLED exhibited a luminance of 9,800 cd / m 2 And the current density is 26.1mA / cm 2 Green light emission.

[0151] [Comparative Device Example 2] OLED using conventional compounds

[0152] An OLED was manufactured in the same manner as in Device Example 1, except that Compound T-1 was used to form a hole transport layer, and Compounds H-2 and H-3 were used as hosts. The manufactured OLED showed a luminance of 2,800 cd / m 2 And the current density is 141.2mA / cm 2 of blue light emission.

[0153] As demonstrated by the device examples, the compounds of the organic electronic materials of the present invention have better light emission characteristics than conventional compounds. The organic electroluminescent device comprising the compounds of the organic electronic materials of the present invention shows superiority in light emission characteristics and lifespan.

[0154]

Table 2

[0155]

Claims

1. An organic electroluminescent compound, which is represented by the following formula 1: in Ar1 represents phenyl, biphenyl, terphenyl, naphthyl, 9,9-dimethyl-9H-fluorenyl, naphthylphenyl or phenylnaphthyl; Ar2 represents biphenyl, terphenyl, naphthyl, 9,9-dimethyl-9H-fluorenyl, naphthylphenyl or phenylnaphthyl; Ar3 and Ar4 each independently represent phenyl, biphenyl, naphthyl, naphthylphenyl or phenylnaphthyl; Ar5 represents methyl, phenyl, dibenzothienyl or dibenzofuranyl; L1 represents a single bond; L2 represents a methyl group or a phenyl group; R1 and R2 each independently represent hydrogen or deuterium; n and m each independently represent 0 or 1, with the restriction that n and m cannot be 0 at the same time; a represents an integer of 3; when a is an integer of 2 or greater, each R1 may be the same or different; b represents an integer of 6; when b is an integer of 2 or greater, each R2 may be the same or different.

2. The organic electroluminescent compound according to claim 1, wherein the compound of formula 1 is represented by any one of the following formulas 2 to 4: in Ar1 to Ar5, L1, L2, R1, R2, a and b are as described in claim 1.

3. The organic electroluminescent compound according to claim 1, wherein the compound of formula 1 is selected from the group consisting of: An organic electroluminescent device comprising the organic electroluminescent compound according to claim 1 .

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