Organic compound and organic electroluminescent device containing the same

Abstract

The present invention relates to a novel organic compound and an organic light-emitting element comprising the organic compound. More specifically, the present invention provides an organic electroluminescent element with low driving voltage and significantly improved luminous efficiency and lifespan.

Description

Technical Field

[0001] The present invention relates to an organic compound and an organic electroluminescent element containing the organic compound. Background Art

[0002] Compared with other flat panel display elements such as existing liquid crystal displays (LCDs), plasma display panels (PDPs) and field emission displays (FEDs), organic electroluminescent elements (OLEDs) have a simple structure and various advantages in the manufacturing process. They have high brightness and excellent viewing angle characteristics, fast response speed and low driving voltage. Therefore, they are being actively developed and commercialized, making them applicable to flat panel displays such as wall-mounted TVs or display backlights, lighting, billboards, etc.

[0003] As for organic electroluminescent elements, CW Tang et al. of Eastman Kodak Company reported the initial organic EL element (CW Tang SAVanslyke, Applied Physics Letters, Vol. 51, p. 913, 1987). The luminescence principle thereof is generally based on that, when voltage is applied, holes injected from the anode and electrons injected from the cathode recombine to form excitons as electron-hole pairs, and the energy of the excitons is converted into light by transferring it to the luminescent material.

[0004] More specifically, an organic electroluminescent element has a structure comprising a cathode (electron injection electrode) and an anode (hole injection electrode), and one or more organic layers between the two electrodes. Starting from the anode, the organic electroluminescent element is stacked in the order of a hole injection layer (HIL), a hole transport layer (HTL), a light emitting layer (EML), an electron transport layer (ETL), or an electron injection layer (EIL). To improve the efficiency of the light emitting layer, a hole transport auxiliary layer or a hole blocking layer (HBL) may be further included before and after the light emitting layer.

[0005] The light-emitting layer is composed of two substances: a host material and a dopant. The dopant needs to have high quantum efficiency. It is preferred that the energy gap of the host material is larger than that of the dopant material so that energy transfer to the dopant can occur easily.

[0006] As existing blue dopant substances, fluorescent molecules such as perylene, coumarine, anthracene, and pyrene are used in a large proportion. However, the half-width (full width half the maximum) of the emission spectrum of these dopants is as wide as approximately 40nm, making it difficult to produce deep blue. In the previous light-emitting element, even if the specified wavelength range is increased through optical resonance, optical loss will occur.

[0007] To address this issue, boron-based dopants, which offer a narrow emission spectrum and high efficiency, have recently become popular. However, despite their high efficiency and excellent color reproduction, they suffer from a short lifespan, leading to an urgent need to improve their lifespan performance.

[0008] Prior art literature

[0009] Patent Literature

[0010] (Non-Patent Document 1) Krebs, Frederik C., et al., "Synthesis, Structure, and Properties of 4,8,12-Trioxa-12c-phospha-4,8,12,12c-tetrahydrodibenzo[cd,mn]pyrene, a Molecular Pyroelectric," Journal of the American Chemical Society, 119.6 (1997): 1208-1216. Summary of the Invention

[0011] Problems to be solved by the invention

[0012] An object of the present invention is to provide a novel organic compound and an organic electroluminescent device comprising the organic compound.

[0013] Another object of the present invention is to provide a novel compound that can be used as a light-emitting layer material. As an organic compound, the novel compound can maintain high efficiency and excellent color expression compared to existing boron-based dopants and can also improve lifespan.

[0014] Another object of the present invention is to provide an organic electroluminescent element that utilizes the above-mentioned organic compound, maintains the excellent properties of the boron dopant, and solves the problem of reduced lifespan through a host material / dopant combination suitable for the blue series of AM-OLEDs.

[0015] Means used to solve problems

[0016] To achieve the above object, the present invention provides a compound represented by the following Chemical Formula 1:

[0017] [Chemical Formula 1]

[0018]

[0019] in,

[0020] n and m are the same as or different from each other and are each independently an integer from 0 to 3,

[0021] X1 and X2 are the same as or different from each other and are each independently selected from the group consisting of NR3, O and S,

[0022] Y is B,

[0023] Ring A is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms,

[0024] R1 to R3 are the same as or different from each other and are each independently selected from hydrogen, cyano, trifluoromethyl, nitro, halogen, hydroxy, substituted or unsubstituted alkylthio having 1 to 4 carbon atoms, substituted or unsubstituted alkyl having 1 to 30 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 carbon atoms, substituted or unsubstituted alkenyl having 2 to 30 carbon atoms, substituted or unsubstituted alkynyl having 2 to 24 carbon atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 2 to 60 carbon atoms, substituted or unsubstituted cycloalkyl having 6 to 30 carbon atoms, The group consisting of a substituted or unsubstituted heteroarylalkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted alkylamino group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 30 carbon atoms, a substituted or unsubstituted aralkylamino group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylamino group having 2 to 24 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, and a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, and the group can bond with adjacent groups to form a substituted or unsubstituted ring,

[0025] At least one of R1 and R2 is a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms.

[0026] The present invention also relates to an organic light-emitting element comprising: a first electrode; a second electrode opposing the first electrode; and one or more organic layers interposed between the first electrode and the second electrode. The one or more organic layers contain one or more compounds according to Chemical Formula 1.

[0027] In the present invention, unless otherwise specified, "hydrogen" means hydrogen, protium, deuterium or tritium.

[0028] In the present invention, "halogen" is fluorine, chlorine, bromine or iodine.

[0029] In the present invention, "alkyl" refers to a monovalent substituent derived from a linear or branched saturated hydrocarbon having 1 to 40 carbon atoms. Examples include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, isopentyl, and hexyl.

[0030] In the present invention, "alkenyl" refers to a monovalent substituent derived from a linear or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and having one or more carbon-carbon double bonds. Examples include, but are not limited to, vinyl, allyl, isopropenyl, and 2-butenyl.

[0031] In the present invention, "alkynyl" refers to a monovalent substituent derived from a linear or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and having one or more carbon-carbon triple bonds. Examples include, but are not limited to, ethynyl and 2-propynyl.

[0032] In the present invention, the "alkylthio group" refers to the above-mentioned alkyl group bonded via a sulfur bond (-S-).

[0033] In the present invention, "aryl" refers to a monovalent substituent derived from a single ring or two or more rings containing 6 to 60 carbon atoms in an aromatic hydrocarbon. Furthermore, it may include two or more rings in a pendant or fused form. Examples of such aryl groups include, but are not limited to, phenyl, naphthyl, phenanthrenyl, anthracenyl, fluorenyl, and dimethylfluorenyl.

[0034] In the present invention, "heteroaryl" refers to a monovalent substituent derived from a monocyclic or polycyclic aromatic hydrocarbon having 6 to 30 carbon atoms. In this case, one or more carbons, preferably 1 to 3 carbons, in the ring are substituted by heteroatoms such as N, O, S or Se. In addition, two or more rings may be included in a pendant or fused form, and may also be included in a form fused to an aryl group. Examples of such heteroaryl groups include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl, polycyclic rings such as phenoxathienyl, indolizinyl, indolyl, purinyl, quinolyl, benzothiazole, and carbazolyl, as well as 2-furyl, N-imidazolyl, 2-isoxazolyl, 2-pyridyl, and 2-pyrimidinyl, but are not limited thereto.

[0035] In the present invention, "aryloxy" is a monovalent substituent represented by RO-, where R is an aryl group having 6 to 60 carbon atoms. Examples of such aryloxy groups include, but are not limited to, phenoxy, naphthyloxy, and diphenoxy.

[0036] In the present invention, "alkyloxy" refers to a monovalent substituent represented by R'O-, where R' represents an alkyl group having 1 to 40 carbon atoms, and may have a linear, branched, or cyclic structure. Examples of alkyloxy groups include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, tert-butoxy, n-butoxy, and pentoxy.

[0037] In the present invention, "alkoxy" can be a straight chain, a branched chain or a cyclic chain. The number of carbon atoms in the alkoxy group is not particularly limited, and preferably has 1 to 20 carbon atoms. Specifically, it can be a methoxy group, an ethoxy group, a n-propoxy group, an isopropoxy group, an isopropoxy group (i-propyloxy), a n-butoxy group, an isobutoxy group, a tert-butoxy group, a sec-butoxy group, a n-pentoxy group, a neopentoxy group, an isopentoxy group, a n-hexyloxy group, a 3,3-dimethylbutoxy group, a 2-ethylbutoxy group, a n-octyloxy group, a n-nonyloxy group, a n-decyloxy group, a benzyloxy group, a p-methylbenzyloxy group, etc., but is not limited thereto.

[0038] As used herein, "aralkyl" refers to an aryl-alkyl group as described above, consisting of an aryl group and an alkyl group. Preferred aralkyl groups include lower alkyl groups. Non-limiting examples of preferred aralkyl groups include benzyl, 2-phenylethyl, and naphthylmethyl. The bond to the parent residue is through the alkyl group.

[0039] In the present invention, the "arylamino group" refers to an amine substituted with an aryl group having 6 to 30 carbon atoms.

[0040] In the present invention, "alkylamino" refers to an amine substituted with an alkyl group having 1 to 30 carbon atoms.

[0041] In the present invention, the "aralkylamino group" refers to an amine substituted with an aryl-alkyl group having 6 to 30 carbon atoms.

[0042] In the present invention, "heteroarylamino" refers to an amino group substituted with an aryl group having 6 to 30 carbon atoms and a heterocyclic group.

[0043] In the present invention, "heteroaralkyl" refers to an aryl-alkyl group substituted by a heterocyclyl group.

[0044] In the present invention, "cycloalkyl" refers to a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms. Examples of such cycloalkyl groups include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, norbornyl, and adamantine.

[0045] In the present invention, "heterocycloalkyl" refers to a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 carbon atoms, wherein one or more carbon atoms, preferably 1 to 3 carbon atoms, in the ring are substituted with heteroatoms such as N, O, S, or Se. Examples of such heterocycloalkyl groups include, but are not limited to, morpholine and piperazine.

[0046] In the present invention, an "alkylsilyl group" refers to a silyl group substituted by an alkyl group having 1 to 40 carbon atoms, and an "arylsilyl group" refers to a silyl group substituted by an aryl group having 6 to 60 carbon atoms.

[0047] In the present invention, the "fused ring" refers to a fused aliphatic ring, a fused aromatic ring, a fused heteroaliphatic ring, a fused heteroaromatic ring, or a combination thereof.

[0048] In the present invention, “bonding to an adjacent group to form a ring” means bonding to an adjacent group to form a substituted or unsubstituted aliphatic hydrocarbon ring; a substituted or unsubstituted aromatic hydrocarbon ring; a substituted or unsubstituted aliphatic heterocycle; a substituted or unsubstituted aromatic heterocycle; or a condensed ring thereof.

[0049] In the present invention, examples of the "aromatic hydrocarbon ring" include phenyl, naphthyl, anthracenyl and the like, but are not limited thereto.

[0050] In the present invention, "aliphatic heterocycle" refers to an aliphatic ring containing one or more heteroatoms.

[0051] In the present invention, the "aromatic heterocycle" refers to an aromatic ring containing one or more heteroatoms.

[0052] In the present invention, “boron-based element”, “boron-based compound”, and “boron-based dopant” refer to a compound or dopant containing the boron (B) element having an atomic number of 5.

[0053] In the present invention, as used herein, "substituted" means that a hydrogen atom bonded to a carbon atom of a compound is replaced by another substituent. The position of substitution is not limited as long as it is a position where a hydrogen atom can be substituted, i.e., a position where a substituent is substitutable. When two or more substituents are substituted, the two or more substituents may be the same or different. The above substituents may be substituted by one or more substituents selected from the group consisting of, but not limited to, hydrogen, cyano, nitro, halogen, hydroxyl, alkyl having 1 to 30 carbon atoms, alkenyl having 2 to 30 carbon atoms, alkynyl having 2 to 24 carbon atoms, heteroalkyl having 2 to 30 carbon atoms, aralkyl having 6 to 30 carbon atoms, aryl having 5 to 30 carbon atoms, heteroaryl having 2 to 30 carbon atoms, heteroarylalkyl having 3 to 30 carbon atoms, alkoxy having 1 to 30 carbon atoms, alkylamino having 1 to 30 carbon atoms, arylamino having 6 to 30 carbon atoms, aralkylamino having 6 to 30 carbon atoms, and heteroarylamino having 2 to 24 carbon atoms.

[0054] Effects of the Invention

[0055] The organic compound of the present invention can maintain low driving voltage and high efficiency and improve lifespan compared to existing boron-based dopants, and can be used as a light-emitting layer material.

[0056] Furthermore, the above-mentioned organic compound can maintain the excellent properties of the boron dopant and solve the problem of reduced life of the organic electroluminescent element by using a host material / dopant combination suitable for the blue series of AM-OLED. DETAILED DESCRIPTION

[0057] Hereinafter, the embodiments of the present invention will be described in detail to facilitate implementation by those skilled in the art. However, the present invention can be implemented in various forms and is not limited to the embodiments described in this specification.

[0058] The organic compound of the present invention contains a non-aromatic six-membered ring in the molecule and has a twisted structure rather than a planar structure. In particular, it includes a cycloalkyl group as a substituent. Compared with previous boron-based dopants, it is an organic compound that can maintain a low driving voltage and high efficiency while improving the life span and can be used as a light-emitting layer material.

[0059] Specifically, the compound of the present invention can be represented by the following Chemical Formula 1:

[0060] [Chemical Formula 1]

[0061]

[0062] in,

[0063] n and m are the same as or different from each other and are each independently an integer from 0 to 3,

[0064] X1 and X2 are the same as or different from each other and are independently selected from the group consisting of NR3, O and S, Y is B,

[0065] Ring A is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms,

[0066] R1 to R3 are the same as or different from each other and are each independently selected from hydrogen, cyano, trifluoromethyl, nitro, halogen, hydroxy, substituted or unsubstituted alkylthio having 1 to 4 carbon atoms, substituted or unsubstituted alkyl having 1 to 30 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 carbon atoms, substituted or unsubstituted alkenyl having 2 to 30 carbon atoms, substituted or unsubstituted alkynyl having 2 to 24 carbon atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 2 to 60 carbon atoms, substituted or unsubstituted cycloalkyl having 6 to 30 carbon atoms, The group consisting of a substituted or unsubstituted heteroarylalkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted alkylamino group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 30 carbon atoms, a substituted or unsubstituted aralkylamino group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylamino group having 2 to 24 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, and a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, and the group can bond with adjacent groups to form a substituted or unsubstituted ring,

[0067] At least one of R1 and R2 is a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms.

[0068] The compound represented by the chemical formula 1 is a compound represented by the following chemical formula 2 or 3, wherein:

[0069] [Chemical Formula 2]

[0070]

[0071] [Chemical Formula 3]

[0072]

[0073] [Chemical Formula 4]

[0074]

[0075] in,

[0076] n, m, Y, X1, X2, R1, R2 and ring A are the same as those in claim 1,

[0077] o and p are the same as or different from each other and are each independently an integer from 0 to 4,

[0078] * is the bonding part,

[0079] In the chemical formula 2, *1 and *2 or *1 and * 2' Bonded with chemical formula 4,

[0080] In the chemical formula 3, *1 and *2 or *1 and * 2' Bonded to chemical formula 4, * a and* b or* a and* b' Bonded with chemical formula 4,

[0081] Ar1 and Ar2 are the same as or different from each other and are each independently selected from hydrogen, cyano, trifluoromethyl, nitro, halogen, hydroxy, substituted or unsubstituted alkylthio having 1 to 4 carbon atoms, substituted or unsubstituted alkyl having 1 to 30 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 carbon atoms, substituted or unsubstituted alkenyl having 2 to 30 carbon atoms, substituted or unsubstituted alkynyl having 2 to 24 carbon atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 2 to 60 carbon atoms, substituted or unsubstituted 6 to 30 carbon atoms, the group consisting of a substituted or unsubstituted heteroarylalkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted alkylamino group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 30 carbon atoms, a substituted or unsubstituted aralkylamino group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylamino group having 2 to 24 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, and a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, and can bond with adjacent groups to form a substituted or unsubstituted ring,

[0082] R4 and R5 are the same as or different from each other and are each independently selected from hydrogen, cyano, trifluoromethyl, nitro, halogen, hydroxy, substituted or unsubstituted alkylthio having 1 to 4 carbon atoms, substituted or unsubstituted alkyl having 1 to 30 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 carbon atoms, substituted or unsubstituted alkenyl having 2 to 30 carbon atoms, substituted or unsubstituted alkynyl having 2 to 24 carbon atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 2 to 60 carbon atoms, substituted or unsubstituted cycloalkyl having 6 to 30 carbon atoms, The group consisting of a substituted or unsubstituted heteroarylalkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted alkylamino group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 30 carbon atoms, a substituted or unsubstituted aralkylamino group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylamino group having 2 to 24 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, and a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, and can bond to adjacent groups to form a substituted or unsubstituted ring.

[0083] The compound represented by Chemical Formula 1 may be more specifically a compound represented by the following Chemical Formula 8 or 9, wherein:

[0084] [Chemical Formula 8]

[0085]

[0086] [Chemical Formula 9]

[0087]

[0088] in,

[0089] n, m, o, p, X1, X2, Y, R1, R2, R4, R5, Ar1 and Ar2 are as defined in Chemical Formulas 1 to 4,

[0090] p', Ar1', Ar2' and R5' are the same as p, Ar1, Ar2 and R5.

[0091] The ring A is selected from the group consisting of the following chemical formulae 5 to 7, wherein:

[0092] [Chemical Formula 5]

[0093]

[0094] [Chemical Formula 6]

[0095]

[0096] [Chemical Formula 7]

[0097]

[0098] in,

[0099] * is the bonding part,

[0100] q is an integer from 0 to 4,

[0101] r and s are integers from 0 to 2,

[0102] X3 and X4 are selected from the group consisting of NR9, O and S,

[0103] R6 to R9 are the same as or different from each other and are each independently selected from hydrogen, cyano, trifluoromethyl, nitro, halogen, hydroxy, substituted or unsubstituted alkylthio having 1 to 4 carbon atoms, substituted or unsubstituted alkyl having 1 to 30 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 carbon atoms, substituted or unsubstituted alkenyl having 2 to 30 carbon atoms, substituted or unsubstituted alkynyl having 2 to 24 carbon atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 2 to 60 carbon atoms, substituted or unsubstituted cycloalkyl having 6 to 30 carbon atoms, The group consisting of a substituted or unsubstituted heteroarylalkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted alkylamino group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 30 carbon atoms, a substituted or unsubstituted aralkylamino group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylamino group having 2 to 24 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, and a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, and can bond to adjacent groups to form a substituted or unsubstituted ring.

[0104] At least one of R1 to R8 is a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, preferably a cycloalkyl group having 5 to 20 carbon atoms, and more preferably a cycloalkyl group having 6 to 20 carbon atoms.

[0105] The compound represented by Chemical Formula 1 according to the present invention may be represented by the following compounds, but is not limited thereto:

[0106]

[0107]

[0108]

[0109]

[0110]

[0111]

[0112] The organic compound of the present invention can be effectively used as a material for forming a light-emitting layer. When the organic compound is prepared into a desired form for forming a light-emitting layer, the light-emitting layer-forming material may further contain commonly added materials such as a host material.

[0113] The light-emitting layer-forming material may be a dopant material.

[0114] The present invention also relates to a light-emitting layer-forming material comprising the above-mentioned organic compound.

[0115] When the above-mentioned organic compound is prepared into a desired form for forming a light-emitting layer, the above-mentioned material for forming the light-emitting layer may further contain a commonly added material, such as a host material.

[0116] In addition, the present invention relates to an organic electroluminescent element, wherein one or more organic thin film layers including at least a light-emitting layer are stacked between a cathode and an anode, wherein the light-emitting layer comprises a compound represented by the following chemical formula 1:

[0117] [Chemical Formula 1]

[0118]

[0119] in,

[0120] n and m are the same as or different from each other and are each independently an integer from 0 to 3,

[0121] X1 and X2 are the same as or different from each other and are independently selected from the group consisting of NR3, O and S, Y is B,

[0122] Ring A is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms,

[0123] R1 to R3 are the same as or different from each other and are each independently selected from hydrogen, cyano, trifluoromethyl, nitro, halogen, hydroxy, substituted or unsubstituted alkylthio having 1 to 4 carbon atoms, substituted or unsubstituted alkyl having 1 to 30 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 carbon atoms, substituted or unsubstituted alkenyl having 2 to 30 carbon atoms, substituted or unsubstituted alkynyl having 2 to 24 carbon atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 2 to 60 carbon atoms, substituted or unsubstituted cycloalkyl having 6 to 30 carbon atoms, The group consisting of a substituted or unsubstituted heteroarylalkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted alkylamino group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 30 carbon atoms, a substituted or unsubstituted aralkylamino group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylamino group having 2 to 24 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, and a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, and the group can bond with adjacent groups to form a substituted or unsubstituted ring,

[0124] At least one of R1 and R2 is a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms.

[0125] The organic electroluminescent element may have a structure of stacked anode, hole injection layer, hole transport layer, light emitting layer, electron transport layer, electron injection layer and cathode, and may further include an electron blocking layer, hole blocking layer and the like as needed.

[0126] The organic electroluminescent device of the present invention is described below with examples, but the following examples do not limit the organic electroluminescent device of the present invention.

[0127] The organic electroluminescent element of the present invention may have a structure in which an anode (hole injection electrode), a hole injection layer (HIL), a hole transport layer (HTL), a light-emitting layer (EML), and a cathode (electron injection electrode) are stacked in this order. Preferably, an electron blocking layer (EBL) may be further included between the anode and the light-emitting layer, and an electron transport layer (ETL) and an electron injection layer (EIL) may be further included between the cathode and the light-emitting layer. In addition, a hole blocking layer (HBL) may also be included between the cathode and the light-emitting layer.

[0128] As the preparation method of organic electroluminescent element of the present invention, first anode material is applied to substrate surface with a conventional method to form anode. At this time, the substrate used is preferably a glass substrate or a transparent plastic substrate having excellent transparency, surface smoothness, ease of handling and water resistance. In addition, as anode material, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO 2 ), zinc oxide (ZnO) etc., which are transparent and have excellent conductivity, can be used.

[0129] Next, a hole injection layer (HIL) material is vacuum-evaporated or spin-coated on the surface of the anode by conventional methods to form a hole injection layer. Examples of such hole injection layer materials include copper phthalocyanine (CuPc), 4,4',4"-tris(3-methylphenylamino)triphenylamine (m-MTDATA), 4,4',4"-tris(3-methylphenylamino)phenoxybenzene (m-MTDAPB), starburst amines such as 4,4',4"-tris(N-carbazolyl)triphenylamine (TCTA), 4,4',4"-tris(N-(2-naphthyl)-N-phenylamino)-triphenylamine (2-TNATA), or IDE406 available from Idemitsu Corporation.

[0130] A hole transport layer (HTL) material is formed on the surface of the hole injection layer by conventional vacuum thermal deposition or spin coating. Examples of the HTL material include bis(N-(1-naphthyl-n-phenyl))benzidine (α-NPD), N,N'-di(Naphthalene-1-yl)-N,N'-biphenyl-benzidine (NPB), or N,N'-biphenyl-N,N'-bis(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine (TPD).

[0131] The light-emitting layer (EML) material is formed by vacuum thermal evaporation or spin coating on the surface of the hole transport layer using conventional methods. As for the dopant in the light-emitting layer material that can be used simultaneously with the light-emitting host material, the compound represented by the above formula 1 of the present invention is preferably used.

[0132] Optionally, an electron blocking layer (EBL) may be further formed between the hole transport layer and the light emitting layer.

[0133] An electron transport layer (ETL) material is formed on the surface of the light emitting layer by conventional vacuum thermal evaporation or spin coating. The ETL material used is not particularly limited, but tris(8-hydroxyquinoline)aluminum (Alq3) is preferably used.

[0134] Optionally, a hole blocking layer (HBL) is further formed between the light emitting layer and the electron transport layer, and a phosphorescent dopant is simultaneously used in the light emitting layer to prevent triplet excitons or holes from diffusing to the electron transport layer.

[0135] The hole blocking layer can be formed by vacuum thermal evaporation and spin coating of the hole blocking layer material by conventional methods. There is no particular limitation on the hole blocking layer material, but preferably, (8-hydroxyquinoline) lithium (Liq), bis(8-hydroxy-2-methylquinoline)-biphenyloxyaluminum (BAlq), bathocuproine (BCP) and lithium fluoride (LiF) are used.

[0136] An electron injection layer (EIL) is formed by vacuum evaporation or spin coating of an electron injection layer (EIL) material on the surface of the electron transport layer using conventional methods. The electron injection layer material used can be LiF, Liq, Li2O, BaO, NaCl, CsF, etc.

[0137] A cathode material is vacuum-evaporated on the surface of the electron injection layer by a conventional method to form a cathode.

[0138] In this case, the cathode material used may be lithium (Li), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium (Mg), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), etc. Furthermore, for front-emitting organic electroluminescent elements, indium tin oxide (ITO) or indium zinc oxide (IZO) may be used to form a transparent cathode that transmits light.

[0139] A covering layer (CPL) can be formed on the surface of the cathode using a covering layer-forming composition.

[0140] Representative examples are given below to illustrate the synthesis methods of the above compounds. However, the synthesis methods of the compounds of the present invention are not limited to the methods exemplified below, and the compounds of the present invention can be prepared by the methods exemplified below and methods known in the art.

[0141] [Synthesis Example 1: Preparation of Compound 1]

[0142]

[0143] After 1.31g (2.00mmol) of starting material 1-1 was dissolved in o-dichlorobenzene (15ml), 1.48g (4.00mmol) of BI3 was added under a nitrogen atmosphere, the temperature was raised from room temperature to 160°C, and stirred for 12 hours. The reaction solution was cooled to room temperature, and the organic layer was extracted with ethyl acetate and water. After removing the solvent of the extracted organic layer, it was purified by silica gel column chromatography (dichloromethane / n-hexane (DCM / Hexane)). After recrystallization and purification with a mixed solvent of dichloromethane / acetone (DCM / Acetone), 0.25g of the above-mentioned compound 1 was obtained in an 18.7% yield.

[0144] MS (MALDI-TOF) m / z: 661[M]+

[0145] [Synthesis Example 2: Preparation of Compound 2]

[0146]

[0147] 0.23 g of the above-mentioned compound 2 was obtained in a yield of 16.5% by the same method as in Synthesis Example 1 except that 1.36 g of the starting material 2-1 was used.

[0148] MS (MALDI-TOF) m / z: 687[M]+

[0149] [Synthesis Example 3: Preparation of Compound 3]

[0150]

[0151] 0.22 g of the above-mentioned compound 3 was obtained in a yield of 15.5% by the same method as in Synthesis Example 1 except that 1.39 g of the starting material 3-1 was used.

[0152] MS (MALDI-TOF) m / z:703[M]+

[0153] [Synthesis Example 4: Preparation of Compound 4]

[0154]

[0155] 0.25 g of the above-mentioned compound 4 was obtained in a yield of 16.2% by the same method as in Synthesis Example 1 except that 1.49 g of the starting material 4-1 was used.

[0156] MS (MALDI-TOF) m / z:755[M]+

[0157] [Synthesis Example 5: Preparation of Compound 5]

[0158]

[0159] 0.26 g of the above-mentioned compound 5 was obtained in a yield of 18.8% by the same method as in Synthesis Example 1 except that 1.39 g of the starting material 5-1 was used.

[0160] MS (MALDI-TOF) m / z:703[M]+

[0161] [Synthesis Example 6: Preparation of Compound 6]

[0162]

[0163] 0.24 g of the above-mentioned compound 6 was obtained in a yield of 17.9% by the same method as in Synthesis Example 1 except that 1.31 g of the starting material 6-1 was used.

[0164] MS (MALDI-TOF) m / z: 661[M]+

[0165] [Synthesis Example 7: Preparation of Compound 7]

[0166]

[0167] 0.26 g of the above-mentioned compound 7 was obtained in a yield of 18.1% by the same method as in Synthesis Example 1 except that 1.42 g of the starting material 7-1 was used.

[0168] MS (MALDI-TOF) m / z:717[M]+

[0169] [Synthesis Example 8: Preparation of Compound 8]

[0170]

[0171] 0.25 g of the above-mentioned compound 8 was obtained in a yield of 17.9% by the same method as in Synthesis Example 1 except that 1.36 g of the starting material 8-1 was used.

[0172] MS (MALDI-TOF) m / z: 687[M]+

[0173] [Synthesis Example 9: Preparation of Compound 9]

[0174]

[0175] 0.26 g of the above-mentioned compound 9 was obtained in a yield of 18.0% by the same method as in Synthesis Example 1 except that 1.42 g of the starting material 9-1 was used.

[0176] MS (MALDI-TOF) m / z:717[M]+

[0177] [Synthesis Example 10: Preparation of Compound 10]

[0178]

[0179] 0.28 g of the compound 10 was obtained in a yield of 19.7% by the same method as in Synthesis Example 1 except that 1.42 g of the starting material 10-1 was used.

[0180] MS (MALDI-TOF) m / z:717[M]+

[0181] [Synthesis Example 11: Preparation of Compound 11]

[0182]

[0183] 0.31 g of the above compound 11 was obtained in a yield of 21.5% by the same method as in Synthesis Example 1 except that 1.43 g of the starting material 11-1 was used.

[0184] MS (MALDI-TOF) m / z:721[M]+

[0185] [Synthesis Example 12: Preparation of Compound 13]

[0186]

[0187] Under N2 conditions, 18.37g (20.0mmol) of starting material 13-1 and 3.80mL (40.0mmol) of boron tribromide were added to a 1000mL flask containing ortho-dichlorobenzene (400ml). Afterwards, the temperature was raised to 80°C and stirred for 3 hours, then raised to 180°C and stirred for 12 hours. The reaction was confirmed to be complete by thin layer chromatography. After the reaction solution was cooled to room temperature, water was added and the organic layer was extracted with ethyl acetate. The solvent of the extracted organic layer was dried with MgSO4, filtered and concentrated, and purified by silica gel column chromatography (dichloromethane / hexane). Afterwards, the product was recrystallized and purified using a mixed solvent of dichloromethane / acetone to obtain 4.71g of the above-mentioned compound 13 with a yield of 25.4%.

[0188] MS (MALDI-TOF) m / z:926[M]+

[0189] [Synthesis Example 13: Preparation of Compound 15]

[0190]

[0191] 0.16 g of the compound 15 was obtained in a yield of 11.1% by the same method as in Synthesis Example 1 except that 1.46 g of the starting material 15-1 was used.

[0192] MS (MALDI-TOF) m / z:737[M]+

[0193] [Synthesis Example 14: Preparation of Compound 16]

[0194]

[0195] 0.14 g of the compound 16 was obtained in a yield of 8.7% by the same method as in Synthesis Example 1 except that 1.61 g of the starting material 16-1 was used.

[0196] MS (MALDI-TOF) m / z: 813[M]+

[0197] [Synthesis Example 15: Preparation of Compound 19]

[0198]

[0199] 0.19 g of the compound 19 was obtained in a yield of 11.5% by the same method as in Synthesis Example 1 except that 1.65 g of the starting material 19-1 was used.

[0200] MS (MALDI-TOF) m / z: 831[M]+

[0201] [Synthesis Example 16: Preparation of Compound 22]

[0202]

[0203] 0.15 g of the compound 22 was obtained in a yield of 9.1% by the same method as in Synthesis Example 1 except that 1.64 g of the starting material 22-1 was used.

[0204] MS (MALDI-TOF) m / z: 827[M]+

[0205] [Synthesis Example 17: Preparation of Compound 23]

[0206]

[0207] 4.62 g of the above-mentioned compound 23 was obtained in a yield of 21.4% by the same method as in Synthesis Example 12 except that 21.41 g of the starting material 23-1 was used.

[0208] MS (MALDI-TOF) m / z: 1078[M]+

[0209] [Synthesis Example 18: Preparation of Compound 32]

[0210]

[0211] 6.44 g of the compound 32 was obtained in a yield of 34.7% by the same method as in Synthesis Example 12 except that 18.41 g of the starting material 32-1 was used.

[0212] MS (MALDI-TOF) m / z:928[M]+

[0213] [Synthesis Example 19: Preparation of Compound 33]

[0214]

[0215] 5.38 g of the above-mentioned compound 33 was obtained in a yield of 29.8% by the same method as in Synthesis Example 12 except that 17.89 g of the starting material 33-1 was used.

[0216] MS (MALDI-TOF) m / z:902[M]+

[0217] [Synthesis Example 20: Preparation of Compound 36]

[0218]

[0219] 0.25 g of the compound 36 was obtained in a yield of 18.6% by the same method as in Synthesis Example 1 except that 1.34 g of the starting material 36-1 was used.

[0220] MS (MALDI-TOF) m / z: 679[M]+

[0221] [Synthesis Example 21: Preparation of Compound 49]

[0222]

[0223] 0.23 g of the above-mentioned compound 49 was obtained in a yield of 15.5% by the same method as in Synthesis Example 1 except that 1.45 g of the starting material 58-1 was used.

[0224] MS (MALDI-TOF) m / z: 661[M]+

[0225] [Synthesis Example 22: Preparation of Compound 59]

[0226]

[0227] 0.19 g of the compound 59 was obtained in a yield of 16.4% by the same method as in Synthesis Example 1 except that 1.15 g of the starting material 59-1 was used.

[0228] MS (MALDI-TOF) m / z: 581[M]+

[0229] [Synthesis Example 23: Preparation of Compound 63]

[0230]

[0231] 0.24 g of the compound 63 was obtained in a yield of 17.4% by the same method as in Synthesis Example 1 except that 1.37 g of the starting material 63-1 was used.

[0232] MS (MALDI-TOF) m / z: 695[M]+

[0233] [Synthesis Example 24: Preparation of Compound 64]

[0234]

[0235] 0.24 g of the above-mentioned compound 64 was obtained in a yield of 16.9% by the same method as in Synthesis Example 1 except that 1.41 g of the starting material 64-1 was used.

[0236] MS (MALDI-TOF) m / z:711[M]+

[0237] [Synthesis Example 25: Preparation of Compound 69]

[0238]

[0239] 0.27 g of the compound 69 was obtained in a yield of 18.8% by the same method as in Synthesis Example 1 except that 1.42 g of the starting material 69-1 was used.

[0240] MS (MALDI-TOF) m / z:744[M]+

[0241] [Synthesis Example 26: Preparation of Compound 76]

[0242]

[0243] 0.30 g of the above-mentioned compound 76 was obtained in a yield of 20.1% by the same method as in Synthesis Example 1 except that 1.50 g of the starting material 76-1 was used.

[0244] MS (MALDI-TOF) m / z:757[M]+

[0245] [Synthesis Example 27: Preparation of Compound 77]

[0246]

[0247] 0.30 g of the compound 77 was obtained in a yield of 19.3% by the same method as in Synthesis Example 1 except that 1.53 g of the starting material 77-1 was used.

[0248] MS (MALDI-TOF) m / z:773[M]+

[0249] [Synthesis Example 28: Preparation of Compound 78]

[0250]

[0251] 4.70 g of the above-mentioned compound 78 was obtained in a yield of 24.5% by the same method as in Synthesis Example 12 except that 19.05 g of the starting material 78-1 was used.

[0252] MS (MALDI-TOF) m / z:960[M]+

[0253] [Synthesis Example 29: Preparation of Compound 79]

[0254]

[0255] 4.90 g of the compound 79 was obtained in a yield of 25.1% by the same method as in Synthesis Example 12 except that 19.37 g of the starting material 79-1 was used.

[0256] MS (MALDI-TOF) m / z:976[M]+

[0257] [Synthesis Example 30: Preparation of Compound 88]

[0258]

[0259] 0.22 g of the above-mentioned compound 88 was obtained in a yield of 15.8% by the same method as in Synthesis Example 1 except that 1.37 g of the starting material 88-1 was used.

[0260] MS (MALDI-TOF) m / z: 695[M]+

[0261] [Synthesis Example 31: Preparation of Compound 89]

[0262]

[0263] 0.24 g of the compound 89 was obtained in a yield of 17.1% by the same method as in Synthesis Example 1 except that 1.41 g of the starting material 89-1 was used.

[0264] MS (MALDI-TOF) m / z:711[M]+

[0265] [Synthesis Example 32: Preparation of Compound 99]

[0266]

[0267] 0.20 g of the compound 99 was obtained in a yield of 15.5% by the same method as in Synthesis Example 1 except that 1.27 g of the starting material 99-1 was used.

[0268] MS (MALDI-TOF) m / z: 645[M]+

[0269] [Synthesis Example 33: Preparation of Compound 101]

[0270]

[0271] 0.22 g of the compound 101 was obtained in a yield of 16.2% by the same method as in Synthesis Example 1 except that 1.35 g of the starting material 101-1 was used.

[0272] MS (MALDI-TOF) m / z: 683[M]+

[0273] [Synthesis Example 34: Preparation of Compound 103]

[0274]

[0275] 0.22 g of the compound 103 was obtained in a yield of 16.4% by the same method as in Synthesis Example 1 except that 1.313 g of the starting material 103-1 was used.

[0276] MS (MALDI-TOF) m / z: 665[M]+

[0277] [Synthesis Example 35: Preparation of Compound 112]

[0278]

[0279] 3.80 g of the compound 112 was obtained in a yield of 23.0% by the same method as in Synthesis Example 12 except that 16.36 g of the starting material 112-1 was used.

[0280] MS (MALDI-TOF) m / z: 826[M]+

[0281] [Synthesis Example 36: Preparation of Compound 113]

[0282]

[0283] 3.39 g of the compound 113 was obtained in a yield of 18.2% by the same method as in Synthesis Example 12 except that 18.45 g of the starting material 113-1 was used.

[0284] MS (MALDI-TOF) m / z:930[M]+

[0285] [Synthesis Example 37: Preparation of Compound 114]

[0286]

[0287] 4.28 g of the compound 114 was obtained in a yield of 25.7% by the same method as in Synthesis Example 12 except that 16.48 g of the starting material 114-1 was used.

[0288] MS (MALDI-TOF) m / z: 832[M]+

[0289] [Synthesis Example 38: Preparation of Compound 115]

[0290]

[0291] 4.53 g of the compound 115 was obtained in a yield of 26.7% by the same method as in Synthesis Example 12 except that 16.80 g of the starting material 115-1 was used.

[0292] MS (MALDI-TOF) m / z: 848[M]+

[0293] [Synthesis Example 39: Preparation of Compound 118]

[0294]

[0295] 0.17 g of the compound 118 was obtained in a yield of 13.2% by the same method as in Synthesis Example 1 except that 1.28 g of the starting material 118-1 was used.

[0296] MS (MALDI-TOF) m / z: 647[M]+

[0297] [Synthesis Example 40: Preparation of Compound 119]

[0298]

[0299] 0.19 g of the compound 119 was obtained in a yield of 14.5% by the same method as in Synthesis Example 1 except that 1.31 g of the starting material 119-1 was used.

[0300] MS (MALDI-TOF) m / z: 661[M]+

[0301] [Synthesis Example 41: Preparation of Compound 122]

[0302]

[0303] 0.13 g of the compound 122 was obtained in a yield of 9.2% by the same method as in Synthesis Example 1 except that 1.43 g of the starting material 122-1 was used.

[0304] MS (MALDI-TOF) m / z:723[M]+

[0305] [Synthesis Example 42: Preparation of Compound 123]

[0306]

[0307] 0.13 g of the compound 123 was obtained in a yield of 8.8% by the same method as in Synthesis Example 1 except that 1.46 g of the starting material 123-1 was used.

[0308] MS (MALDI-TOF) m / z:737[M]+

[0309] [Synthesis Example 43: Preparation of Compound 129]

[0310]

[0311] 0.25 g of the compound 129 was obtained in a yield of 16.1% by the same method as in Synthesis Example 1 except that 1.52 g of the starting material 129-1 was used.

[0312] MS (MALDI-TOF) m / z:767[M]+

[0313] [Synthesis Example 44: Preparation of Compound 132]

[0314]

[0315] 4.31 g of the compound 132 was obtained in a yield of 26.5% by the same method as in Synthesis Example 12 except that 16.12 g of the starting material 132-1 was used.

[0316] MS (MALDI-TOF) m / z: 814[M]+

[0317] [Synthesis Example 45: Preparation of Compound 133]

[0318]

[0319] 3.32 g of the compound 133 was obtained in a yield of 19.9% ​​by the same method as in Synthesis Example 12 except that 16.52 g of the starting material 133-1 was used.

[0320] MS (MALDI-TOF) m / z: 834[M]+

[0321] [Synthesis Example 46: Preparation of Compound 134]

[0322]

[0323] 4.71 g of the compound 134 was obtained in a yield of 27.8% by the same method as in Synthesis Example 12 except that 16.80 g of the starting material 134-1 was used.

[0324] MS (MALDI-TOF) m / z: 848[M]+

[0325] [Synthesis Example 47: Preparation of Compound 135]

[0326]

[0327] 4.86 g of the compound 135 was obtained in a yield of 28.1% by the same method as in Synthesis Example 12 except that 17.12 g of the starting material 135-1 was used.

[0328] MS (MALDI-TOF) m / z: 864[M]+

[0329] [Synthesis Example 48: Preparation of Compound 138]

[0330]

[0331] 2.76 g of the compound 138 was obtained in a yield of 18.6% by the same method as in Synthesis Example 12 except that 14.68 g of the starting material 138-1 was used.

[0332] MS (MALDI-TOF) m / z:742[M]+

[0333] [Synthesis Example 49: Preparation of Compound 139]

[0334]

[0335] 2.64 g of the compound 139 was obtained in a yield of 17.4% by the same method as in Synthesis Example 12 except that 15.00 g of the starting material 139-1 was used.

[0336] MS (MALDI-TOF) m / z:758[M]+

[0337] [Synthesis Example 50: Preparation of Compound 147]

[0338]

[0339] 5.03 g of the above-mentioned compound 147 was obtained in a yield of 32.1% by the same method as in Synthesis Example 12 except that 15.52 g of the starting material 147-1 was used.

[0340] MS (MALDI-TOF) m / z:784[M]+

[0341] [Synthesis Example 51: Preparation of Compound 148]

[0342]

[0343] 4.09 g of the compound 148 was obtained in a yield of 25.6% by the same method as in Synthesis Example 12 except that 15.80 g of the starting material 148-1 was used.

[0344] MS (MALDI-TOF) m / z:798[M]+

[0345] [Synthesis Example 52: Preparation of Compound 157]

[0346]

[0347] 3.33 g of the compound 157 was obtained in a yield of 21.7% by the same method as in Synthesis Example 12 except that 15.20 g of the starting material 157-1 was used.

[0348] MS (MALDI-TOF) m / z:768[M]+

[0349] [Synthesis Example 53: Preparation of Compound 164]

[0350]

[0351] 2.84 g of the compound 164 was obtained in a yield of 19.7% by the same method as in Synthesis Example 12 except that 14.28 g of the starting material 164-1 was used.

[0352] MS (MALDI-TOF) m / z:722[M]+

[0353] [Synthesis Example 54: Preparation of Compound 168]

[0354]

[0355] 3.22 g of the compound 168 was obtained in a yield of 18.4% by the same method as in Synthesis Example 12 except that 17.34 g of the starting material 168-1 was used.

[0356] MS (MALDI-TOF) m / z: 875[M]+

[0357] [Synthesis Example 55: Preparation of Compound 169]

[0358]

[0359] 3.20 g of the compound 169 was obtained in a yield of 18.6% by the same method as in Synthesis Example 12 except that 17.02 g of the starting material 169-1 was used.

[0360] MS (MALDI-TOF) m / z: 859[M]+

[0361] [Comparative Example 1: Preparation of Compound A]

[0362]

[0363] 0.16 g of the above-mentioned compound A was obtained in a yield of 18.0% by the same method as in Synthesis Example 1 except that 0.89 g of the starting material A-1 was used.

[0364] MS (MALDI-TOF) m / z:452[M]+

[0365] [Comparative Example 2: Preparation of Compound B]

[0366]

[0367] 0.19 g of the above-mentioned compound B was obtained in a yield of 19.1% by the same method as in Synthesis Example 1 except that 0.95 g of the starting material B-1 was used.

[0368] MS (MALDI-TOF) m / z:484[M]+

[0369] [Comparative Example 3: Preparation of Compound C]

[0370]

[0371] 3.09 g of the above-mentioned compound C was obtained in a yield of 23.4% by the same method as in Synthesis Example 12 except that 13.04 g of the starting material C-1 was used.

[0372] MS (MALDI-TOF) m / z: 660[M]+

[0373] [Comparative Example 4: Preparation of Compound D]

[0374]

[0375] 1.90 g of the comparative compound 4 was obtained in a yield of 15.2% by the same method as in Synthesis Example 12 except that 12.36 g of the starting material was used.

[0376] MS (MALDI-TOF) m / z: 626[M]+

[0377] [Example 1: Preparation of organic electroluminescent element]

[0378] A substrate layered with 100nm of ITO (the anode of the organic electroluminescent element) was patterned using photolithography to define the cathode, anode, and insulating layer. To improve the work function and clean the anode (ITO), UV ozone treatment and O2:N2 plasma surface treatment were then performed. A 10nm thick HAT-CN layer was formed on top as a hole injection layer (HIL). Next, a hole transport layer was formed by vacuum evaporating N4,N4,N4',N4'-tetra([1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4,4'-diamine to a thickness of 90 nm on the hole injection layer. , N-phenyl-N-(4-(spiro[benzo[de]anthracene-7,9'-fluorene]-2'-yl]phenyl)dibenzo[b,d]furan-4-amine was formed to a thickness of 15 nm as an electron blocking layer (EBL). On top of the electron blocking layer (EBL), α,β-ADN(9-(naphthalene-1-yl)-10-(naphthalene-2-yl)anthracene) was evaporated as the host material of the light-emitting layer, and 2% of compound 1 was doped as a dopant to form a 25 nm thick light-emitting layer (EML).

[0379] On top of this, a 25nm thick mixture of 2-(4-(9,10-di(naphthalene-2-yl)anthracen-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole and Liq (mixed in a 1:1 weight ratio) was vapor-deposited as an electron transport layer (ETL). A 1nm thick electron injection layer was vapor-deposited on top of this electron transport layer, and 100nm of aluminum was vapor-deposited as a cathode. A seal cap containing a getter was then attached using a UV-curable adhesive to protect the organic electroluminescent element from atmospheric oxygen and moisture, resulting in the production of an organic electroluminescent element.

[0380] [Examples 2 to 55: Preparation of organic electroluminescent elements]

[0381] An organic electroluminescent element was prepared in the same manner as in Example 1, except that compounds 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 13, 15, 16, 19, 22, 23, 59, 63, 64, 69, 76, 77, 78, 79, 88, 32, 33, 36, 58, 99, 101, 103, 112, 113, 114, 115, 118, 119, 122, 123, 129, 132, 133, 134, 135, 138, 139, 147, 148, 157, 164, 168 and 169 were used as dopants instead of the above compound 1.

[0382] [Comparative Examples 1 to 4: Preparation of Organic Electroluminescent Elements]

[0383] Organic electroluminescent elements were prepared in the same manner as in Example 1, except that Compounds A to D4 were used instead of Compound 1 as the dopant.

[0384] [Experimental Example: Characteristic Analysis of Organic Electroluminescent Elements]

[0385] Next, a 10 mA / cm 2 The current is used to detect the electro-optical characteristics, and the current is 10mA / cm 2 The lifespan was tested by constant current driving, and the test results are shown and compared in Table 1 below.

[0386] [Table 1]

[0387]

[0388]

[0389]

[0390] Comparative Examples 1 to 4 are compounds containing a non-aromatic six-membered ring (cycloolefin ring) containing N in the molecule, and have the same characteristics as the present invention, that is, they are compounds having a distorted structure rather than a planar structure. Inventive Examples 1 to 55 have the same structural characteristics, except that they include a cycloalkyl group as a substituent.

[0391] Table 1 shows the driving voltage, external quantum efficiency and life characteristics of the organic electroluminescent elements including the comparative example and example compounds. It can be seen that the driving voltage, external quantum efficiency and life characteristics of the organic electroluminescent elements show great differences depending on the structural differences between the compounds.

[0392] The preferred embodiments of the present invention are described in detail above, but the scope of the present invention is not limited thereto. Various modifications and improvements made by those skilled in the art using the basic concepts of the present invention defined in the claims fall within the scope of the present invention.

Claims

1. A compound selected from any one of the compounds having the following structures, 2. An organic light-emitting element, wherein: include: the first electrode, a second electrode, facing the first electrode, one or more organic layers, disposed between the first electrode and the second electrode; Wherein, at least one of the organic layers comprises at least one compound according to claim 1 .

3. The organic light emitting element according to claim 2, wherein The organic layer is selected from the group consisting of a hole injection layer, a hole transport layer, a light emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer.

4. The organic light-emitting element according to claim 2, wherein The organic layer is a light-emitting layer, The light-emitting layer contains the compound according to claim 1 as a dopant.

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