Organic light-emitting compound and organic electroluminescent element using the same

Abstract

The present invention relates to novel organic light-emitting compounds and organic electroluminescent elements using the same, and more specifically, to compounds having excellent thermal stability, electrochemical stability, luminescence ability, and hole / electron transport ability, and to organic electroluminescent elements having improved characteristics such as luminescence efficiency, driving voltage, and life span by including the compounds in one or more organic layers.

Description

Technical Field

[0001] The present invention relates to novel organic light-emitting compounds and organic electroluminescent elements using the same. More specifically, it relates to compounds with excellent thermal stability, electrochemical stability and hole transport ability, and organic electroluminescent elements with improved properties such as luminous efficiency, driving voltage and life by including the compounds in one or more organic layers. Background Art

[0002] When an organic electroluminescent element (hereinafter referred to as an "organic EL element") applies current or voltage between two electrodes, holes are injected from the anode into the organic layer, and electrons are injected from the cathode into the organic layer. When the injected holes and electrons meet, excitons are formed, and the excitons transition to the ground state and emit light. At this time, the substances used for the organic layer can be divided into luminescent substances, hole injection substances, hole transport substances, electron transport substances, electron injection substances, etc. according to their functions.

[0003] The luminescent materials of organic EL elements can be divided into blue, green, and red luminescent materials according to the luminescent color. In addition, it can be divided into yellow and orange luminescent materials for presenting more natural colors. In addition, in order to increase the color purity and increase the luminescent efficiency through energy transfer, a host / doping system can be used as a luminescent material. Doping materials can be divided into fluorescent dopants using organic substances and phosphorescent dopants using metal coordination compounds containing heavy atoms such as Ir and Pt. Since the development of phosphorescent materials can theoretically increase the luminescent efficiency by up to 4 times compared to fluorescence, not only phosphorescent dopants but also phosphorescent host materials have received attention.

[0004] So far, NPB, BCP, Alq3, etc. represented by the following chemical formula are widely known as hole injection layer, hole transport layer, hole blocking layer, and electron transport layer materials. As for luminescent materials, anthracene derivatives have been reported as fluorescent host / dopant materials. In particular, as phosphorescent materials with great advantages in improving efficiency among luminescent materials, metal coordination compounds containing Ir, such as Firpic, Ir(ppy)3, (acac)Ir(btp)2, have been used as blue, green, and red phosphorescent doping materials. Nowadays, CBP shows excellent characteristics as a phosphorescent host material.

[0005] However, although the conventional materials have advantages in terms of light-emitting properties, they have low glass transition temperatures and very poor thermal stability, so they cannot achieve satisfactory lifespans for organic EL elements. Therefore, it is necessary to develop organic layer materials with excellent performance. Summary of the invention

[0006] Technical issues

[0007] An object of the present invention is to provide a novel organic compound that can be applied to an organic electroluminescent device and that has excellent thermal stability, electrochemical stability, and hole transporting ability and can be used as a hole transporting layer material.

[0008] Another object of the present invention is to provide an organic electroluminescent element which comprises the novel organic compound and exhibits low driving voltage and high luminous efficiency and has an improved lifespan.

[0009] Solution to the problem

[0010] In order to achieve the above object, the present invention provides a compound represented by the following chemical formula 1:

[0011] [Chemical formula 1]

[0012]

[0013] (In the above chemical formula 1,

[0014] X is O or S,

[0015] a and b are each an integer from 0 to 4,

[0016] R1 and R2 are the same or different from each other and are independently selected from hydrogen, deuterium, halogen, cyano, nitro, amino, C1-C 40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 atomic nuclei, C6~C 60 aryl, heteroaryl with 5 to 60 atomic nuclei, C1~C 40 Alkoxy, C6~C 60 Aryloxy, C1~C 40 Alkyl silyl, C6~C 60 Aryl silyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, C6~C 60 Arylphosphine, C6~C 60 The aryl phosphine oxide group and C6~C 60 A group consisting of arylamine groups,

[0017] Ring A is C6~C 40 Polycyclic aromatic rings,

[0018] n1 to n3 are each an integer from 0 to 3,

[0019] L1 to L3 are the same or different from each other and are independently selected from a single bond, C6 to C 18 and a heteroarylene group having 5 to 18 atomic nuclei,

[0020] Ar1 and Ar2 are the same or different from each other and are independently selected from C6 to C 60 A group consisting of an aryl group and a heteroaryl group having 5 to 60 atomic nuclei,

[0021] The polycyclic aromatic ring of the A ring, the arylene and heteroarylene groups of L1 to L3, the aryl and heteroaryl groups of Ar1 and Ar2, and the alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, alkoxy, aryloxy, alkylsilyl, arylsilyl, alkylboryl, arylboryl, arylphosphino, arylphosphine oxide and arylamine groups of R1 to R2 are each independently selected from hydrogen, deuterium, halogen, cyano, nitro, C1~C 40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 nuclei, C6~C 60 aryl, heteroaryl with 5 to 60 nuclei, C1~C 40 Alkoxy, C6~C 60 Aryloxy, C1~C 40 Alkyl silyl, C6~C 60 Aryl silyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, C6~C 60 Arylphosphine, C6~C 60 The aryl phosphine oxide group and C6~C 60 The arylamine group is substituted or unsubstituted with one or more substituents. In this case, when there are multiple substituents, they are the same as or different from each other).

[0022] In addition, the present invention provides an organic electroluminescent element, which comprises (i) an anode, (ii) a cathode and (iii) one or more organic layers between the anode and the cathode, wherein at least one of the one or more organic layers comprises the compound represented by the above Chemical Formula 1.

[0023] Effects of the Invention

[0024] The compound of the present invention is excellent in thermal stability, electrochemical stability and hole transporting ability, and therefore can be effectively used as an organic layer material of an organic electroluminescent device.

[0025] Furthermore, an organic electroluminescent device whose organic layer contains the compound of the present invention has greatly improved light emitting performance, driving voltage, life, efficiency, etc. and can be effectively applied to full-color display panels and the like. BRIEF DESCRIPTION OF THE DRAWINGS

[0026] Figure 1 This is a cross-sectional view schematically showing an organic electroluminescent element according to an example of the present invention.

[0027] Figure 2 This is a cross-sectional view schematically showing an organic electroluminescent element according to another example of the present invention.

[0028] **Explanation of symbols**

[0029] 100: anode 200: cathode

[0030] 300: organic layer 310: hole injection layer

[0031] 320: hole transport layer 330: light emitting layer

[0032] 340: electron transport layer 350: electron injection layer DETAILED DESCRIPTION

[0033] Hereinafter, the present invention will be described in detail.

[0034] <New Compounds>

[0035] The present invention provides a novel organic compound which has excellent electrochemical stability, thermal stability, and carrier transporting ability (especially hole transporting ability) and can be used as a highly efficient hole transporting layer material.

[0036] Specifically, the compound represented by Chemical Formula 1 of the present invention includes a core structure having the following constitution: a monocyclic or polycyclic aromatic ring such as a benzene ring or a naphthalene ring is condensed at the benzene site on one side of the fluorene within the spiro[condensed aromatic ring condensed with fluorene - xanthene] portion or the spiro[condensed aromatic ring condensed with fluorene - thioxathene] portion, and an amine group substituted with an aryl group and / or a heteroaryl group is introduced directly or through a linker at the benzene site on the other side of the fluorene.

[0037] The compound of the above chemical formula 1 is condensed with a monocyclic or polycyclic aromatic ring such as a benzene ring or a naphthalene ring in the benzene part on one side of the fluorene in the spiro [condensed aromatic ring-xanthene condensed with fluorene] part or the spiro [condensed aromatic ring-thioxanthene condensed with fluorene] part, so that the hole mobility is high and the hole transport ability is excellent. In addition, the compound of the above chemical formula 1 has a HOMO energy level in the range of about 5.0 to 5.6 eV and a LUMO energy level in the range of about 1.7 to 2.5 eV. It is between the HOMO and LUMO energy levels of the hole injection layer and the light-emitting layer, so that the hole injection and transfer are smooth. Therefore, in the case where the organic electroluminescent element includes the compound of the present invention as a hole transport layer material, not only the luminous efficiency of the organic electroluminescent element can be improved, but also the life span can be improved due to the low driving voltage.

[0038] In addition, the compound of the above chemical formula 1 can further improve the luminous efficiency due to the physicochemical characteristics such as amorphous characteristics and high refractive index characteristics by introducing an amine group substituted with an aryl group and / or a heteroaryl group into the benzene part on the other side of the fluorene in the spiro [condensed aromatic ring condensed with fluorene - xanthene] part or the spiro [condensed aromatic ring condensed with fluorene - thioxathene] part. In addition, the glass transition temperature (Tg) of the compound of the above chemical formula 1 is high, so it is not only excellent in stability but also excellent in electrochemical stability.

[0039] As described above, the compound represented by Chemical Formula 1 of the present invention has excellent thermal stability, electrochemical stability, and hole transport properties. Therefore, the compound represented by Chemical Formula 1 of the present invention can be used as an organic layer material of an organic electroluminescent element, preferably as a hole transport layer material or a hole transport auxiliary layer material, and more preferably as a hole transport layer material. The performance and life characteristics of an organic electroluminescent element containing such a compound of the present invention can be greatly improved, and the performance of a full-color organic light-emitting panel using such an organic electroluminescent element will also be maximized.

[0040] In the compound represented by the above chemical formula 1, X is O or S. Such a compound of the chemical formula 1 has excellent amphoteric properties of electrons and holes and excellent carrier transport ability compared to the case where X is N or C. Therefore, when the compound of the chemical formula 1 of the present invention is used as a hole transport layer material, the efficiency and driving voltage improvement effect can be improved due to the increase in hole transport ability.

[0041] In addition, in the compound represented by the above Chemical Formula 1, a and b are integers of 0 to 4, respectively.

[0042] Here, when a and b are each 0, it means that hydrogen is not replaced by the substituents R1 and R2, respectively. When a and b are each an integer from 1 to 4, multiple R1 and multiple R2 are the same or different from each other and are independently selected from deuterium, halogen, cyano, nitro, amino, C1~C 40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 atomic nuclei, C6~C 60 aryl, heteroaryl with 5 to 60 atomic nuclei, C1~C 40 Alkoxy, C6~C 60 Aryloxy, C1~C 40 Alkyl silyl, C6~C 60 Aryl silyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, C6~C 60 Arylphosphine, C6~C 60 The aryl phosphine oxide group and C6~C 60 In this case, the heterocycloalkyl group and the heteroaryl group each contain one or more heteroatoms selected from the group consisting of N, S, O and Se. According to one example, a and b are each 0, and R1 and R2 are hydrogen.

[0043] In the compound represented by the above chemical formula 1, ring A is C6 to C 60 The polycyclic aromatic ring may be C6 to C 40 The polycyclic aromatic ring of 40 Here, the rings in the polycyclic aromatic ring may be the same or different from each other. Specifically, examples of the A ring include a naphthalene ring, an anthracene ring, a tetracene ring, a pyrene ring, a phenanthrene ring, a phenalene ring, a benzoanthracene ring, a benzopyrene ring, a triphenylene ring, The present invention includes, but is not limited to, a chrysene ring, a pentaphene ring, a pentacene ring, and a condensed ring between the two rings.

[0044] According to one example, the compound represented by the above Chemical Formula 1 can be specifically represented by the following Chemical Formula 2, but is not limited thereto.

[0045] [Chemical formula 2]

[0046]

[0047] In the above chemical formula 2,

[0048] X, R1, R2, a, b, L1 to L3, n1 to n3, Ar1 and Ar2 are each the same as defined in the above Chemical Formula 1,

[0049] B ring is C6~C 40 Monocyclic aromatic ring or C6~C 40 The polycyclic aromatic ring may be preferably a benzene ring, a naphthalene ring, an anthracene ring, a tetracene ring, a pyrene ring, a phenanthrene ring, a phenalene ring, a benzoanthracene ring, a benzopyrene ring, a triphenylene ring, The polycyclic aromatic rings may be the same as or different from each other.

[0050] More specifically, the compound represented by Chemical Formula 1 of the present invention may be embodied as a compound represented by any one of the following Chemical Formulas 3 to 5, but is not limited thereto.

[0051] [Chemical formula 3]

[0052]

[0053] [Chemical formula 4]

[0054]

[0055] [Chemical formula 5]

[0056]

[0057] In the above chemical formulas 3 to 5,

[0058] X, R1, R2, a, b, L1 to L3, n1 to n3, Ar1 and Ar2 are each the same as defined in the above Chemical Formula 1.

[0059] In addition, in the compound represented by the above Chemical Formula 1, n1 to n3 are each an integer of 0 to 3, and preferably 0 or 1.

[0060] Here, when n1 to n3 are each 0, L1 to L3 are each a single bond. When n1 to n3 are each an integer from 1 to 3, L1 to L3 are divalent linkers, which are the same or different from each other and are independently selected from C6 to C 18 The present invention is a group consisting of an arylene group having an atomic nucleus number of 5 to 18 and a heteroarylene group having an atomic nucleus number of 5 to 18. For example, in the above Chemical Formula 1, L1 to L3 are the same as or different from each other, and each independently may be a single bond or a phenylene group.

[0061] In particular, when L1 is a phenylene group, L1 can be used as the center. Partially In this case, the compound of Chemical Formula 1 can not only maximize the hole transporting ability, but also reduce the driving voltage of the organic electroluminescent element due to the easy hole transfer between molecules.

[0062] In addition, in the compound represented by the above chemical formula 1, Ar1 and Ar2 are the same or different from each other and are independently selected from C6 to C 60 The group consisting of an aryl group and a heteroaryl group having an atomic nucleus number of 5 to 60. For example, Ar1 and Ar2 are the same or different from each other and can be independently selected from the group consisting of the following substituents A-1 to A-3, but are not limited thereto.

[0063]

[0064] In the above chemical formula A-3,

[0065] Y1 is selected from the group consisting of O, S, C(Ar3)(Ar4) and N(Ar5),

[0066] d is an integer from 0 to 4,

[0067] e is an integer from 0 to 3,

[0068] R3 and R4 are the same or different from each other and are independently selected from hydrogen, deuterium, halogen, cyano, nitro, amino, C1-C 40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 atomic nuclei, C6~C 60 aryl, heteroaryl with 5 to 60 atomic nuclei, C1~C 40 Alkoxy, C6~C 60 Aryloxy, C1~C 40 Alkyl silyl, C6~C 60 Aryl silyl, C1~C40 Alkyl boron, C6~C 60 Aryl boron, C6~C 60 Arylphosphine, C6~C 60 The aryl phosphine oxide group and C6~C 60 A group consisting of arylamine groups,

[0069] The alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, alkoxy, aryloxy, alkylsilyl, arylsilyl, alkylboryl, arylboryl, arylphosphino, arylphosphine oxide and arylamine groups of R3 and R4 can be independently selected from hydrogen, deuterium, halogen, cyano, nitro, C1-C 40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 nuclei, C6~C 60 aryl, heteroaryl with 5 to 60 nuclei, C1~C 40 Alkoxy, C6~C 60 Aryloxy, C1~C 40 Alkyl silyl, C6~C 60 Aryl silyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, C6~C 60 Arylphosphine, C6~C 60 The aryl phosphine oxide group and C6~C 60 The arylamine group may be substituted or unsubstituted with one or more substituents selected from deuterium, halogen, cyano, nitro, C1-C 20 Alkyl, C6~C 30 The aryl group or the heteroaryl group having 5 to 30 atomic nuclei may be substituted or unsubstituted with one or more substituents selected from the group consisting of: an aryl group having 1 to 20 atomic nuclei and a heteroaryl group having 5 to 30 atomic nuclei. In this case, when there are multiple substituents, the multiple substituents may be the same or different from each other.

[0070] In addition, in the compound represented by the above chemical formula 1, the polycyclic aromatic ring of the above ring A, the arylene group and heteroarylene group of L1, the aryl group and heteroaryl group of Ar1 and Ar2, and the alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkoxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboryl group, arylboryl group, arylphosphine group, arylphosphine oxide group and arylamine group of R1 to R2 can be independently selected from hydrogen, deuterium, halogen, cyano group, nitro group, C1~C 40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C3~C 40Cycloalkyl, heterocycloalkyl with 3 to 40 nuclei, C6~C 60 aryl, heteroaryl with 5 to 60 nuclei, C1~C 40 Alkoxy, C6~C 60 Aryloxy, C1~C 40 Alkyl silyl, C6~C 60 Aryl silyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, C6~C 60 Arylphosphine, C6~C 60 The aryl phosphine oxide group and C6~C 60 The arylamine group may be substituted or unsubstituted with one or more substituents selected from deuterium, halogen, cyano, nitro, C1-C 20 Alkyl, C6~C 30 The heterocycloalkyl and heteroaryl groups may be substituted or unsubstituted with one or more substituents selected from the group consisting of an aryl group having 5 to 30 atomic nuclei and a heteroaryl group having 5 to 30 atomic nuclei. In this case, when there are multiple substituents, the multiple substituents may be the same or different from each other. Here, the heterocycloalkyl and heteroaryl groups may each contain one or more heteroatoms selected from the group consisting of N, S, O and Se.

[0071] The compound represented by Chemical Formula 1 of the present invention may be specifically represented by the following Chemical Formula 6 or 7, but is not limited thereto.

[0072] [Chemical formula 6]

[0073]

[0074] [Chemical formula 7]

[0075]

[0076] In the above chemical formulas 6 and 7,

[0077] X, R1, R2, a, b, L1 to L3, n1 to n3, Ar1 are each the same as defined in the above chemical formula 1,

[0078] Ring B has the same definition as in the above chemical formula 2,

[0079] c is 0 or 1,

[0080] Y1 is selected from the group consisting of O, S, C(Ar3)(Ar4) and N(Ar5),

[0081] d is an integer from 0 to 4,

[0082] e is an integer from 0 to 3,

[0083] R3, R4, Ar3 to Ar5 are the same or different from each other and are independently selected from hydrogen, deuterium, halogen, cyano, nitro, amino, C1-C 40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 atomic nuclei, C6~C 60 aryl, heteroaryl with 5 to 60 atomic nuclei, C1~C 40 Alkoxy, C6~C 60 Aryloxy, C1~C 40 Alkyl silyl, C6~C 60 Aryl silyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, C6~C 60 Arylphosphine, C6~C 60 The aryl phosphine oxide group and C6~C 60 A group consisting of arylamine groups,

[0084] The monocyclic aromatic ring and the polycyclic aromatic ring of the above-mentioned B ring, the alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, alkoxy, aryloxy, alkylsilyl, arylsilyl, alkylboryl, arylboryl, arylphosphino, arylphosphine oxide and arylamine groups of R3, R4, Ar3 to Ar5 are each independently selected from hydrogen, deuterium, halogen, cyano, nitro, C1~C 40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 nuclei, C6~C 60 aryl, heteroaryl with 5 to 60 nuclei, C1~C 40 Alkoxy, C6~C 60 Aryloxy, C1~C 40 Alkyl silyl, C6~C 60 Aryl silyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, C6~C 60 Arylphosphine, C6~C 60 The aryl phosphine oxide group and C6~C 60 The arylamine group may be substituted or unsubstituted with one or more substituents selected from deuterium, halogen, cyano, nitro, C1-C 20 Alkyl, C6~C 30The aryl group or the heteroaryl group having 5 to 30 atomic nuclei may be substituted or unsubstituted with one or more substituents selected from the group consisting of: an aryl group having 1 to 20 atomic nuclei and a heteroaryl group having 5 to 30 atomic nuclei. In this case, when there are multiple substituents, the multiple substituents may be the same or different from each other.

[0085] The compound represented by Chemical Formula 1 of the present invention may be embodied as a compound represented by any one of the following Chemical Formulas 8 to 13, but is not limited thereto.

[0086] [Chemical formula 8]

[0087]

[0088] [Chemical formula 9]

[0089]

[0090] [Chemical formula 10]

[0091]

[0092] [Chemical formula 11]

[0093]

[0094] [Chemical formula 12]

[0095]

[0096] [Chemical formula 13]

[0097]

[0098] In the above chemical formulas 8 to 13,

[0099] X, R1, R2, a, b, L2 to L3, n1 to n3, Ar1 are each the same as defined in Chemical Formula 1,

[0100] Y1, c, d, e, R3, and R4 are each the same as defined in the above chemical formulas 6 to 7.

[0101] The compound represented by Chemical Formula 1 of the present invention may be embodied as a compound represented by any one of the following Chemical Formulas 14 to 22, but is not limited thereto.

[0102] [Chemical formula 14]

[0103]

[0104] [Chemical formula 15]

[0105]

[0106] [Chemical formula 16]

[0107]

[0108] [Chemical formula 17]

[0109]

[0110] [Chemical formula 18]

[0111]

[0112] [Chemical formula 19]

[0113]

[0114] [Chemical formula 20]

[0115]

[0116] [Chemical formula 21]

[0117]

[0118] [Chemical formula 22]

[0119]

[0120] In the above chemical formulas 14 to 22,

[0121] X, R1, R2, a, b, n1 to n3 are each the same as defined in the above Chemical Formula 1,

[0122] Y1, c, d, e, R3, and R4 are each the same as defined in the above chemical formulas 6 to 7.

[0123] f is 0 or 1,

[0124] Y2 is selected from the group consisting of O, S, C(Ar6)(Ar7) and N(Ar8),

[0125] g is an integer from 0 to 4,

[0126] h is an integer from 0 to 3,

[0127] R5, R6 and Ar6 to Ar8 are the same or different from each other and are independently selected from hydrogen, deuterium, halogen, cyano, nitro, amino, C1-C 40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 atomic nuclei, C6~C 60 aryl, heteroaryl with 5 to 60 atomic nuclei, C1~C 40Alkoxy, C6~C 60 Aryloxy, C1~C 40 Alkyl silyl, C6~C 60 Aryl silyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, C6~C 60 Arylphosphine, C6~C 60 The aryl phosphine oxide group and C6~C 60 A group consisting of arylamine groups,

[0128] The alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, alkoxy, aryloxy, alkylsilyl, arylsilyl, alkylboryl, arylboryl, arylphosphino, arylphosphine oxide and arylamine groups of R5, R6 and Ar6 to Ar8 can be independently selected from hydrogen, deuterium, halogen, cyano, nitro, C1~C 40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 nuclei, C6~C 60 aryl, heteroaryl with 5 to 60 nuclei, C1~C 40 Alkoxy, C6~C 60 Aryloxy, C1~C 40 Alkyl silyl, C6~C 60 Aryl silyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, C6~C 60 Arylphosphine, C6~C 60 The aryl phosphine oxide group and C6~C 60 The arylamine group may be substituted or unsubstituted with one or more substituents selected from deuterium, halogen, cyano, nitro, C1-C 20 Alkyl, C6~C 30 The aryl group or the heteroaryl group having 5 to 30 atomic nuclei may be substituted or unsubstituted with one or more substituents selected from the group consisting of: an aryl group having 1 to 20 atomic nuclei and a heteroaryl group having 5 to 30 atomic nuclei. In this case, when there are multiple substituents, the multiple substituents may be the same or different from each other.

[0129] The compound represented by the chemical formula 1 of the present invention described above can be embodied as the compounds exemplified below, such as compound (1) to compound (259), but is not limited to these compounds.

[0130]

[0131]

[0132]

[0133]

[0134]

[0135]

[0136]

[0137]

[0138] In the present invention, "alkyl" means a monovalent substituent derived from a linear or branched saturated hydrocarbon having 1 to 40 carbon atoms. Examples thereof include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, isopentyl, and hexyl.

[0139] In the present invention, "alkenyl" means 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 thereof include vinyl, allyl, isopropenyl, 2-butenyl, etc., but are not limited thereto.

[0140] In the present invention, "alkynyl" means 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 thereof include ethynyl and 2-propynyl, but are not limited thereto.

[0141] In the present invention, "cycloalkyl" means a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms. Examples of such cycloalkyl include cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, and adamantine, but are not limited thereto.

[0142] In the present invention, "heterocycloalkyl" means a monovalent substituent derived from a non-aromatic hydrocarbon having a nucleus number of 3 to 40, 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 include morpholinyl and piperazinyl, but are not limited thereto.

[0143] In the present invention, "aryl" means a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms and composed of a single ring or a combination of two or more rings. In addition, it may also include a form in which two or more rings are simply attached (pendant) or condensed to each other. Examples of such aryl groups include phenyl, naphthyl, phenanthrenyl, anthracenyl, etc., but are not limited thereto.

[0144] In the present invention, "heteroaryl" means a monovalent substituent derived from a monocyclic heterocyclic or polycyclic aromatic hydrocarbon having an atomic nucleus number of 5 to 60. In this case, one or more carbon atoms, preferably 1 to 3 carbon atoms, in the ring are substituted by heteroatoms such as N, O, S or Se. In addition, it may also include a form in which two or more rings are simply attached (pendant) or condensed to each other, and further may include a form condensed with an aromatic 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; and 2-furanyl, N-imidazole, 2-isothiazolyl, and 2-isothiazolyl. oxazolyl, 2-pyridyl, 2-pyrimidinyl, etc., but are not limited thereto.

[0145] In the present invention, "alkoxy" means a monovalent substituent represented by R'O-, wherein R' is an alkyl group having 1 to 40 carbon atoms, and may include a linear, branched or cyclic structure. Examples of such alkoxy groups include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, tert-butoxy, n-butoxy, pentyloxy, and the like.

[0146] In the present invention, "aryloxy" means a monovalent substituent represented by RO-, wherein R is an aryl group having 5 to 40 carbon atoms. Examples of such aryloxy groups include phenoxy, naphthoxy, diphenoxy and the like, but are not limited thereto.

[0147] In the present invention, "alkylsilyl" means a silyl group substituted with an alkyl group having 1 to 40 carbon atoms, including not only a monoalkylsilyl group but also a dialkylsilyl group and a trialkylsilyl group. In addition, "arylsilyl" means a silyl group substituted with an aryl group having 5 to 60 carbon atoms, including not only a monoarylsilyl group but also a diarylsilyl group, a triarylsilyl group and other polyarylsilyl groups.

[0148] In the present invention, the "alkylboryl group" means a boron group substituted by an alkyl group having 1 to 40 carbon atoms, and the "arylboryl group" means a boron group substituted by an aryl group having 6 to 60 carbon atoms.

[0149] In the present invention, "alkylphosphino" means a phosphino group substituted by an alkyl group having 1 to 40 carbon atoms, and includes not only a monoalkylphosphino group but also a dialkylphosphino group. In addition, in the present invention, "arylphosphino" means a phosphino group substituted by a monoaryl group or a diaryl group having 6 to 60 carbon atoms, and includes not only a monoarylphosphino group but also a diarylphosphino group.

[0150] In the present invention, the "arylamine group" means an amine group substituted with an aryl group having 6 to 40 carbon atoms, and includes not only a monoarylamine group but also a diarylamine group.

[0151] <Organic electroluminescent element>

[0152] On the other hand, another aspect of the present invention relates to an organic electroluminescent device (hereinafter, “organic EL device”) including the compound represented by the above Chemical Formula 1.

[0153] Specifically, the organic electroluminescent element of the present invention comprises an anode, a cathode, and one or more organic layers between the anode and the cathode, and at least one of the one or more organic layers comprises the compound represented by the above chemical formula 1. At this time, the above compounds can be used alone or in combination of two or more.

[0154] The one or more organic layers may be any one or more 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, wherein at least one organic layer comprises the compound represented by the above chemical formula 1. Preferably, the organic layer comprising the compound of the above chemical formula 1 may be a hole transport layer.

[0155] According to one example, the one or more organic layers may include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer. The hole transport layer may be a compound represented by the chemical formula 1.

[0156] The compound represented by the above chemical formula 1 can be included in an organic electroluminescent element as a hole transport layer material. In this case, the compound of the above chemical formula 1 has a high glass transition temperature, a high hole mobility and a high hole transport capacity. Due to the appropriate HOMO and LUMO energy levels between the hole injection layer and the light-emitting layer, the hole injection and transfer from the hole injection layer to the light-emitting layer side are smooth, and it has amorphous crystallinity and high refractive index characteristics. Therefore, the efficiency (luminous efficiency and power efficiency), life, brightness, driving voltage, thermal stability, etc. of the organic electroluminescent element containing the compound of the above chemical formula 1 can be improved.

[0157] The structure of the organic electroluminescent element of the present invention is not particularly limited. For example, an anode 100, one or more organic layers 300, and a cathode 200 may be sequentially stacked on a substrate (see Figure 1 and Figure 2 ). In addition, an insulating layer or an adhesive layer may be inserted at the interface between the electrode and the organic layer.

[0158] According to one example, the organic electroluminescent element is Figure 1 As shown, the structure may have an anode 100, a hole injection layer 310, a hole transport layer 320, a light emitting layer 330, an electron transport layer 340 and a cathode 200 stacked in sequence on a substrate. Figure 2 As shown, an electron injection layer 350 may be provided between the electron transport layer 340 and the cathode 200. In addition, a hole blocking layer (not shown) may be provided between the light-emitting layer 330 and the electron transport layer 340. The organic electroluminescent element of the present invention may be formed and manufactured using materials and methods known in the art, except that at least one layer of the organic layer 300 [e.g., the hole transport layer 320] contains the compound represented by the chemical formula 1.

[0159] The organic layer may be formed by vacuum deposition or solution coating, and examples of the solution coating method include spin coating, dip coating, blade coating, inkjet printing, thermal transfer, etc., but are not limited thereto.

[0160] The substrate that can be used in the present invention is not particularly limited, and non-limiting examples include silicon wafers, quartz, glass plates, metal plates, plastic films and sheets, and the like.

[0161] In addition, examples of anode materials include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; conductive polymers such as polythiophene, poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT), polypyrrole, or polyaniline; and carbon black, but are not limited to these.

[0162] In addition, examples of cathode materials include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin or lead, or alloys thereof; and multilayer structure materials such as LiF / Al or LiO2 / Al, but are not limited to these.

[0163] In addition, the hole injection layer, the light emitting layer, the electron transport layer, and the electron injection layer are not particularly limited, and common materials known in the art can be used.

[0164] Hereinafter, the present invention will be described in detail by way of examples. However, the following examples are merely illustrative of the present invention, and the present invention is not limited to the following examples.

[0165] [Preparation Example 1] Synthesis of 9-bromospiro[benzo[c]fluorene-7,9'-xanthene]

[0166]

[0167] After adding 42 mL (0.65 mol) of methanesulfonic acid (MsOH) to 50 g (0.16 mol) of 9-bromo-7H-benzo[c]fluorene-7-one and 152.2 g (1.62 mol) of phenol, the mixed solution was heated to reflux at 120°C for 12 hours. Then, the temperature of the reaction solution obtained by heating and reflux was cooled to room temperature, and 300 mL of purified water was added to the reaction solution to terminate the reaction of the reaction solution. After the reaction was completed, the mixed solution was extracted with 1.0 L of CH2Cl2 and the organic layer was separated. The separated organic layer was neutralized with 500 mL of saturated calcium carbonate and washed with distilled water. After that, the washed organic layer was dried with anhydrous MgSO4, distilled under reduced pressure, and purified by gel column chromatography to obtain 40.3 g (yield 54%) of the target compound.

[0168] 1 H-NMR (in CDCl3): δ7.78 (d, 1H), 7.65 (d, 1H), 7.50 (d, 1H), 7.38 (t, 1H), 7.27 (d, 1H), 7.25 (m, 5H), 7.15 (d, 1H), 6.79 (t, 2H), 6.41 (d, 2H)

[0169] [LCMS]: 461

[0170] [Preparation Example 2] Synthesis of 2-bromospiro[benzo[b]fluorene-11,9'-xanthene]

[0171]

[0172] The same process as in Preparation Example 1 was carried out except that 2-bromo-11H-benzo[b]fluoren-11-one was used instead of 9-bromo-7H-benzo[c]fluoren-7-one to obtain 31.3 g (42%) of the target compound.

[0173] [LCMS]: 461

[0174] [Preparation Example 3] Synthesis of 9-bromospiro[benzo[a]fluorene-11,9'-xanthene]

[0175]

[0176] The same process as in Preparation Example 1 was carried out except that 9-bromo-11H-benzo[a]fluoren-11-one was used instead of 9-bromo-7H-benzo[c]fluoren-7-one used in Preparation Example 1 to obtain 29.1 g (39%) of the target compound corresponding to the structural isomer of Core 1.

[0177] [LCMS]: 461

[0178] [Preparation Example 4] Synthesis of 10-chlorospiro[benzo[c]fluorene-7,9'-xanthene]

[0179]

[0180] The same process as in Preparation Example 1 was carried out except that 10-chloro-7H-benzo[c]fluoren-7-one was used instead of 9-bromo-7H-benzo[c]fluoren-7-one used in Preparation Example 1 to obtain 35.4 g (45%) of the target compound corresponding to the structural isomer of Core 1.

[0181] [LCMS]: 416

[0182] [Preparation Example 5] Synthesis of 11-chlorospiro[benzo[c]fluorene-7,9'-xanthene]

[0183]

[0184] The same process as in Preparation Example 1 was carried out except that 11-chloro-7H-benzo[c]fluoren-7-one was used instead of 9-bromo-7H-benzo[c]fluoren-7-one used in Preparation Example 1 to obtain 37.0 g (47%) of the target compound corresponding to the structural isomer of Core 1.

[0185] [LCMS]: 416

[0186] [Preparation Example 6] Synthesis of 9-bromospiro[benzo[c]fluorene-7,9'-thioxanthene]

[0187]

[0188] The same process as in Preparation Example 1 was carried out except that thiophenol was used instead of phenol, to obtain 45.6 g (59%) of the target compound of Core 6.

[0189] [LCMS]: 477

[0190] [Preparation Example 7] Synthesis of 2-bromospiro[benzo[b]fluorene-11,9'-thioxanthene]

[0191]

[0192] The same process as in the above-mentioned Preparation Example 1 was carried out except that thiophenol was used instead of the phenol used in the above-mentioned Preparation Example 1, and 2-bromo-11H-benzo[b]fluorene-11-one was used instead of 9-bromo-7H-benzo[c]fluorene-7-one, to obtain 42.5 g (55%) of the target compound corresponding to the structural isomer of core 6.

[0193] [Preparation Example 8] Synthesis of 9-bromospiro[benzo[a]fluorene-11,9'-thioxanthenyl]

[0194]

[0195] The same process as in the above-mentioned Preparation Example 1 was carried out except that thiophenol was used instead of the phenol used in the above-mentioned Preparation Example 1, and 9-bromo-11H-benzo[a]fluorene-11-one was used instead of 9-bromo-7H-benzo[c]fluorene-7-one, to obtain 31.7 g (41%) of the target compound corresponding to the structural isomer of core 6.

[0196] [LCMS]: 477

[0197] [Preparation Example 9] Synthesis of 11-chlorospiro[benzo[c]fluorene-7,9'-thioxanthene]

[0198]

[0199] The same process as in the above-mentioned Preparation Example 1 was carried out except that thiophenol was used instead of the phenol used in the above-mentioned Preparation Example 1, and 11-chloro-7H-benzo[c]fluorene-7-one was used instead of 9-bromo-7H-benzo[c]fluorene-7-one, to obtain 40.9 g (50%) of the target compound corresponding to the structural isomer of core 6.

[0200] [LCMS]: 432

[0201] [Preparation Example 10] 4,4,5,5-tetramethyl-2-(spiro[benzo[c]fluorene-7,9'-xanthene]-9-yl)-1,3,2-dioxo Synthesis of Heteroboranes

[0202]

[0203] 500 mL of 1,4-dioxaborolane was added to 25.0 g (54.2 mmol) of 9-bromospiro[benzo[c]fluorene-7,9'-xanthene] obtained in [Preparation Example 1] and 16.5 g (65.1 mmol) of 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bis(1,3,2-dioxaborolane). Then, 2.3 g (2.8 mmol) of [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (II) (Pd(dppf)Cl2) and 16.0 g (163 mmol) of potassium acetate (KOAc) were added to the mixed solution, and then heated to reflux at 130°C for 4 hours. After that, the temperature of the reaction solution obtained by heating and reflux was cooled to room temperature, and 500 mL of ammonium chloride aqueous solution was added to the reaction solution to terminate the reaction, and then extracted with 1.0 L of ethyl acetate (EA), and washed with distilled water to obtain an organic layer. After that, the obtained organic layer was dried with anhydrous MgSO4, distilled under reduced pressure, and purified by gel column chromatography to obtain 18.2 g of the target compound (yield 66%).

[0204] [LCMS]: 508

[0205] [Preparation Example 11] 4,4,5,5-tetramethyl-2-(spiro[benzo[a]fluorene-11,9'-xanthene]-9-yl)-1,3,2-dioxo Synthesis of Heteroboranes

[0206]

[0207] The same process as in Preparation Example 10 was carried out except that 9-bromospiro[benzo[a]fluorene-11,9'-xanthene] obtained in Preparation Example 3 was used instead of 9-bromospiro[benzo[c]fluorene-7,9'-xanthene] used in Preparation Example 10 to obtain 32.8 g (58%) of the target compound corresponding to the structural isomer of Core 10.

[0208] [LCMS]: 508

[0209] [Preparation Example 12] 4,4,5,5-tetramethyl-2-(spiro[benzo[c]fluorene-7,9'-xanthene]-10-yl)-1,3,2-dioxo Synthesis of Heteroboranes

[0210]

[0211] The same process as in Preparation Example 10 was carried out except that 10-chlorospiro[benzo[c]fluorene-7,9'-xanthene] obtained in Preparation Example 4 was used instead of 9-bromospiro[benzo[c]fluorene-7,9'-xanthene] used in Preparation Example 10 to obtain 26.9 g (63%) of the target compound corresponding to the structural isomer of Core 10.

[0212] [LCMS]: 508

[0213] [Preparation Example 13] 4,4,5,5-tetramethyl-2-(spiro[benzo[c]fluorene-7,9'-thioxanthen]-11-yl)-1,3,2-dioxo Synthesis of Heteroboranes

[0214]

[0215] The same process as in Preparation Example 10 was carried out except that 11-chlorospiro[benzo[c]fluorene-7,9'-thioxanthene] obtained in Preparation Example 9 was used instead of 9-bromospiro[benzo[c]fluorene-7,9'-xanthene] used in Preparation Example 10 to obtain 29.5 g (70%) of the target compound corresponding to Core 11.

[0216] [LCMS]: 524

[0217] [Synthesis Example 1] Synthesis of Compound 2

[0218]

[0219] After adding 100 mL of toluene to 10.0 g (21.7 mmol) of 9-bromospiro[benzo[c]fluorene-7,9'-xanthene] obtained in Preparation Example 1 and 7.0 g (21.7 mmol) of di([1,1'-biphenyl]-4-yl)amine, 1.0 g (1.1 mmol) of Pd2(dba)3, 1.04 g (2.2 mmol) of XPhos, and 4.2 g (43.4 mmol) of NaOt-Bu were added to the reaction solution, and heated to reflux at 120°C for 3 hours. Then, the temperature of the reaction solution after heating and reflux was cooled to room temperature, and then 300 mL of purified water was added to the reaction solution to terminate the reaction. The mixed solution obtained after the reaction was extracted with 500 mL of EA and washed with distilled water to obtain an organic layer. The obtained organic layer was dried over anhydrous MgSO 4 , distilled under reduced pressure, and then purified by gel column chromatography to obtain 11.1 g (yield 73%) of the target compound.

[0220] [LCMS]: 701

[0221] [Synthesis Example 2] Synthesis of Compound 4

[0222]

[0223] The same process as in [Synthesis Example 1] was carried out except that N-([1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-2-amine was used instead of di([1,1'-biphenyl]-4-yl)amine used in Synthesis Example 1 to obtain 9.9 g (yield 65%) of the target compound.

[0224] [LCMS]: 701

[0225] [Synthesis Example 3] Synthesis of Compound 7

[0226]

[0227] The same process as in [Synthesis Example 1] was carried out except that N-([1,1'-biphenyl]-2-yl)-9,9-dimethyl-9H-fluoren-2-amine was used instead of di([1,1'-biphenyl]-4-yl)amine used in Synthesis Example 1 to obtain 8.5 g (yield 70%) of the target compound.

[0228] [LCMS]: 741

[0229] [Synthesis Example 4] Synthesis of Compound 11

[0230]

[0231] 600 mL of dioxaborolan was added to 15 g (29.5 mmol) of 4,4,5,5-tetramethyl-2-(spiro[benzo[c]fluorene-7,9'-xanthene]-9-yl)-1,3,2-dioxaborolan in Preparation Example 10 and 15.3 g (32.5 mmol) of N-([1,1'-biphenyl]-4-yl)-N-(4-chlorophenyl)-9,9-dimethyl-9H-fluoren-2-amine. After adding 1.7 g (1.5 mmol) of Pd(PPh3)4 and 12.2 g (88.5 mmol) of K2CO3, the mixture was heated to reflux at 120°C for 3 hours. After that, the temperature of the reaction solution after heating to reflux was cooled to room temperature, and 500 mL of purified water was added to the cooled reaction solution to terminate the reaction. The mixed solution obtained after the reaction was extracted with 1.0 L of EA and washed with distilled water to obtain an organic layer. The obtained organic layer was dried with anhydrous MgSO4, distilled under reduced pressure, and purified by gel column chromatography to obtain 14.2 g (yield 59%) of the target compound.

[0232] [LCMS]: 818

[0233] [Synthesis Example 5] Synthesis of Compound 14

[0234]

[0235] The same process as in [Synthesis Example 1] was carried out except that N-([1,1'-biphenyl]-4-yl)dibenzo[b,d]furan-2-amine was used instead of di([1,1'-biphenyl]-4-yl)amine used in Synthesis Example 1 to obtain 7.7 g (yield 62%) of the target compound.

[0236] [LCMS]: 715

[0237] [Synthesis Example 6] Synthesis of Compound 19

[0238]

[0239] The same process as in [Synthesis Example 1] was carried out except that N-(4-(dibenzo[b,d]furan-4-yl)phenyl)-[1,1'-biphenyl]-4-amine was used instead of di([1,1'-biphenyl]-4-yl)amine used in Synthesis Example 1 to obtain 10.2 g (yield 55%) of the target compound.

[0240] [LCMS]: 791

[0241] [Synthesis Example 7] Synthesis of Compound 25

[0242]

[0243] The same process as in [Synthesis Example 1] was carried out except that N-([1,1'-biphenyl]-4-yl)dibenzo[b,d]thiophene-2-amine was used instead of di([1,1'-biphenyl]-4-yl)amine used in Synthesis Example 1 to obtain 5.2 g (yield 72%) of the target compound.

[0244] [LCMS]: 731

[0245] [Synthesis Example 8] Synthesis of Compound 29

[0246]

[0247] The same process as in [Synthesis Example 1] was carried out except that N-(9,9-dimethyl-9H-fluoren-2-yl)dibenzo[b,d]thiophene-3-amine was used instead of di([1,1'-biphenyl]-4-yl)amine used in Synthesis Example 1 to obtain 6.6 g (yield 75%) of the target compound.

[0248] [LCMS]: 771

[0249] [Synthesis Example 9] Synthesis of Compound 34

[0250]

[0251] The same process as in [Synthesis Example 1] was carried out except that N-(9,9-dimethyl-9H-fluoren-2-yl)dibenzo[b,d]furan-2-amine was used instead of di([1,1'-biphenyl]-4-yl)amine used in Synthesis Example 1 to obtain 9.1 g (yield 64%) of the target compound.

[0252] [LCMS]: 755

[0253] [Synthesis Example 10] Synthesis of Compound 37

[0254]

[0255] The same process as in [Synthesis Example 1] was carried out except that N-([1,1'-biphenyl]-4-yl)-9-phenyl-9H-carbazole-3-amine was used instead of di([1,1'-biphenyl]-4-yl)amine used in Synthesis Example 1 to obtain 8.6 g (yield 69%) of the target compound.

[0256] LCMS]: 790

[0257] [Synthesis Example 11] Synthesis of Compound 42

[0258]

[0259] The same process as in [Synthesis Example 1] was carried out except that N-(dibenzo[b,d]thiophene-4-yl)dibenzo[b,d]furan-4-amine was used instead of di([1,1'-biphenyl]-4-yl)amine used in [Synthesis Example 1] to obtain 10.4 g (yield 61%) of the target compound.

[0260] [LCMS]: 745

[0261] [Synthesis Example 12] Synthesis of Compound 45

[0262]

[0263] The same process as [Synthesis Example 1] was carried out except that 2-bromospiro[benzo[b]fluorene-11,9'-xanthene] of Preparation Example 2 was used instead of 9-bromospiro[benzo[c]fluorene-7,9'-xanthene] used in Synthesis Example 1, and N-([1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-2-amine was used instead of di([1,1'-biphenyl]-4-yl)amine. 4.9 g (yield 75%) of the target compound was obtained.

[0264] [LCMS]: 701

[0265] [Synthesis Example 13] Synthesis of Compound 52

[0266]

[0267] The same process as [Synthesis Example 1] was carried out except that 2-bromospiro[benzo[b]fluorene-11,9'-xanthene] of Preparation Example 2 was used instead of 9-bromospiro[benzo[c]fluorene-7,9'-xanthene] used in Synthesis Example 1, and N-([1,1'-biphenyl]-2-yl)dibenzo[b,d]furan-3-amine was used instead of di([1,1'-biphenyl]-4-yl)amine. 7.5 g (yield 52%) of the target compound was obtained.

[0268] [LCMS]: 715

[0269] [Synthesis Example 14] Synthesis of Compound 54

[0270]

[0271] The same process as [Synthesis Example 1] was carried out except that 2-bromospiro[benzo[b]fluorene-11,9'-xanthene] of Preparation Example 2 was used instead of 9-bromospiro[benzo[c]fluorene-7,9'-xanthene] used in Synthesis Example 1, and 4-(dibenzo[b,d]furan-1-yl)-N-phenylaniline was used instead of di([1,1'-biphenyl]-4-yl)amine. 11.4 g (yield 76%) of the target compound was obtained.

[0272] [LCMS]: 715

[0273] [Synthesis Example 15] Synthesis of Compound 59

[0274]

[0275] The same process as [Synthesis Example 1] was carried out except that 2-bromospiro[benzo[b]fluorene-11,9'-xanthene] of Preparation Example 2 was used instead of 9-bromospiro[benzo[c]fluorene-7,9'-xanthene] used in Synthesis Example 1, and N-([1,1'-biphenyl]-4-yl)dibenzo[b,d]thiophene-1-amine was used instead of di([1,1'-biphenyl]-4-yl)amine. 8.5 g (yield 59%) of the target compound was obtained.

[0276] [LCMS]: 731

[0277] [Synthesis Example 16] Synthesis of Compound 65

[0278]

[0279] The same process as [Synthesis Example 1] was carried out except that 2-bromospiro[benzo[b]fluorene-11,9'-xanthene] of Preparation Example 2 was used instead of 9-bromospiro[benzo[c]fluorene-7,9'-xanthene] used in Synthesis Example 1, and N-([1,1'-biphenyl]-2-yl)-9-phenyl-9H-carbazole-3-amine was used instead of di([1,1'-biphenyl]-4-yl)amine. 3.9 g (yield 71%) of the target compound was obtained.

[0280] [LCMS]: 790

[0281] [Synthesis Example 17] Synthesis of Compound 69

[0282]

[0283] The same process as [Synthesis Example 1] was carried out except that 9-bromospiro[benzo[a]fluorene-11,9'-xanthene] of Preparation Example 3 was used instead of 9-bromospiro[benzo[c]fluorene-7,9'-xanthene] used in Synthesis Example 1, and N-([1,1'-biphenyl]-4-yl)naphthalene-1-amine was used instead of di([1,1'-biphenyl]-4-yl)amine. 5.6 g (yield 62%) of the target compound was obtained.

[0284] [LCMS]: 675

[0285] [Synthesis Example 18] Synthesis of Compound 77

[0286]

[0287] The same process as [Synthesis Example 4] was carried out except that 4,4,5,5-tetramethyl-2-(spiro[benzo[a]fluorene-11,9'-xanthene]-9-yl)-1,3,2-dioxaborane of Preparation Example 11 was used instead of 9-bromospiro[benzo[c]fluorene-7,9'-xanthene] used in Synthesis Example 1, and N-([1,1'-biphenyl]-4-yl)-N-(4-chlorophenyl)dibenzo[b,d]furan-4-amine was used instead of di([1,1'-biphenyl]-4-yl)amine. 10.3 g (yield 66%) of the target compound was obtained.

[0288] [LCMS]: 791

[0289] [Synthesis Example 19] Synthesis of Compound 82

[0290]

[0291] The same process as [Synthesis Example 4] was carried out except that 4,4,5,5-tetramethyl-2-(spiro[benzo[a]fluorene-11,9'-xanthene]-9-yl)-1,3,2-dioxaborane of Preparation Example 11 was used instead of 9-bromospiro[benzo[c]fluorene-7,9'-xanthene] used in Synthesis Example 1, and N-([1,1'-biphenyl]-2-yl)-N-(4-chlorophenyl)dibenzo[b,d]furan-2-amine was used instead of di([1,1'-biphenyl]-4-yl)amine. 7.0 g (yield 62%) of the target compound was obtained.

[0292] [LCMS]: 791

[0293] [Synthesis Example 20] Synthesis of Compound 89

[0294]

[0295] The same process as [Synthesis Example 1] was carried out except that 9-bromospiro[benzo[a]fluorene-11,9'-xanthene] of Preparation Example 3 was used instead of 9-bromospiro[benzo[c]fluorene-7,9'-xanthene] used in Synthesis Example 1, and N-([1,1'-biphenyl]-2-yl)-9-phenyl-9H-carbazole-3-amine was used instead of di([1,1'-biphenyl]-4-yl)amine. 4.5 g (yield 69%) of the target compound was obtained.

[0296] [LCMS]: 790

[0297] [Synthesis Example 21] Synthesis of Compound 94

[0298]

[0299] The 9-bromospiro[benzo[a]fluorene-11,9'-xanthene] of Preparation Example 3 was used instead of the 9-bromospiro[benzo[c]fluorene-7,9'-xanthene] used in Synthesis Example 1, and N-(4-(9-phenyl-9H-carbazole-3-yl)phenyl)-[1,1'-biphenyl]-2-amine was used instead of di([1,1'-biphenyl]-4-yl)amine. Except for this, the same process as [Synthesis Example 1] was carried out to obtain 3.5 g of the target compound (yield 77%).

[0300] [LCMS]: 867

[0301] [Synthesis Example 22] Synthesis of Compound 96

[0302]

[0303] After adding 100 mL of toluene to 12.5 g (30.0 mmol) of 10-chlorospiro[benzo[c]fluorene-7,9'-xanthene] of Preparation Example 4 and 6.6 g (30.0 mmol) of N-phenylnaphthalene-1-amine, 0.34 g (1.5 mmol) of Pd(OAc)2, 1.2 g (2.9 mmol) of P(t-Bu)3, and 5.8 g (60.0 mmol) of NaOt-Bu were added to the reaction solution, and heated to reflux at 120°C for 3 hours. Then, the temperature of the reaction solution after heating and reflux was cooled to room temperature, and 300 mL of purified water was added to the cooled reaction solution to terminate the reaction. The mixed solution obtained after the reaction was extracted with 500 mL of EA, and then washed with distilled water to obtain an organic layer. The obtained organic layer was dried with anhydrous MgSO4, distilled under reduced pressure, and purified by gel column chromatography to obtain 10.4 g of the target compound (yield 58%).

[0304] [LCMS]: 599

[0305] [Synthesis Example 23] Synthesis of Compound 100

[0306]

[0307] The same process as in [Synthesis Example 22] was carried out except that N-([1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-2-amine was used instead of N-phenylnaphthalen-1-amine used in Synthesis Example 22 to obtain 8.4 g (yield 63%) of the target compound.

[0308] [LCMS]: 701

[0309] [Synthesis Example 24] Synthesis of Compound 105

[0310]

[0311] The same procedure as in [Synthesis Example 22] was carried out except that bis(4-(naphthalen-1-yl)phenyl)amine was used instead of N-phenylnaphthalen-1-amine used in Synthesis Example 22 to obtain 5.0 g (yield 49%) of the target compound.

[0312] [LCMS]: 801

[0313] [Synthesis Example 25] Synthesis of Compound 108

[0314]

[0315] The same process as [Synthesis Example 4] was carried out except that 4,4,5,5-tetramethyl-2-(spiro[benzo[c]fluorene-7,9'-xanthene]-10-yl)-1,3,2-dioxaborolane of Preparation Example 12 was used instead of 4,4,5,5-tetramethyl-2-(spiro[benzo[c]fluorene-7,9'-xanthene]-9-yl)-1,3,2-dioxaborolane used in Synthesis Example 4, and N-([1,1'-biphenyl]-4-yl)-N-(4-chlorophenyl)-[1,1'-biphenyl]-2-amine was used instead of N-([1,1'-biphenyl]-4-yl)-N-(4-chlorophenyl)-9,9-dimethyl-9H-fluorene-2-amine. 8.2 g (yield 70%) of the target compound was obtained.

[0316] [LCMS]: 777

[0317] [Synthesis Example 26] Synthesis of Compound 117

[0318]

[0319] The same process as in [Synthesis Example 22] was carried out except that N-(4-(dibenzo[b,d]furan-1-yl)phenyl)-[1,1'-biphenyl]-4-amine was used instead of N-phenylnaphthalen-1-amine used in Synthesis Example 22 to obtain 5.0 g (yield 49%) of the target compound.

[0320] [LCMS]: 791

[0321] [Synthesis Example 27] Synthesis of Compound 122

[0322]

[0323] The same process as in Synthesis Example 22 was carried out except that N-([1,1'-biphenyl]-4-yl)dibenzo[b,d]thiophene-2-amine was used instead of N-phenylnaphthalene-1-amine to obtain 10.5 g (yield 55%) of the target compound.

[0324] [LCMS]: 731

[0325] [Synthesis Example 28] Synthesis of Compound 130

[0326]

[0327] The same process as in [Synthesis Example 22] was carried out except that N-([1,1'-biphenyl]-2-yl)-9-phenyl-9H-carbazole-3-amine was used instead of N-phenylnaphthalen-1-amine used in Synthesis Example 22 to obtain 9.3 g (yield 59%) of the target compound.

[0328] [LCMS]: 790

[0329] [Synthesis Example 29] Synthesis of Compound 139

[0330]

[0331] The same process as [Synthesis Example 22] was carried out except that 11-chlorospiro[benzo[c]fluorene-7,9'-xanthene] of Preparation Example 5 was used instead of 10-chlorospiro[benzo[c]fluorene-7,9'-xanthene] used in Synthesis Example 22, and N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-9H-fluorene-2-amine was used instead of N-phenylnaphthalene-1-amine. 4.5 g (yield 52%) of the target compound was obtained.

[0332] [LCMS]: 741

[0333] [Synthesis Example 30] Synthesis of Compound 153

[0334]

[0335] The same process as [Synthesis Example 22] was carried out except that 11-chlorospiro[benzo[c]fluorene-7,9'-xanthene] of Preparation Example 5 was used instead of 10-chlorospiro[benzo[c]fluorene-7,9'-xanthene] used in Synthesis Example 22, and N-([1,1'-biphenyl]-4-yl)dibenzo[b,d]thiophene-3-amine was used instead of N-phenylnaphthalene-1-amine. 6.6 g (yield 50%) of the target compound was obtained.

[0336] [LCMS]: 731

[0337] [Synthesis Example 31] Synthesis of Compound 161

[0338]

[0339] The same process as [Synthesis Example 22] was carried out except that 11-chlorospiro[benzo[c]fluorene-7,9'-xanthene] of Preparation Example 5 was used instead of 10-chlorospiro[benzo[c]fluorene-7,9'-xanthene] used in Synthesis Example 22, and N-(9,9-dimethyl-9H-fluorene-2-yl)-9-phenyl-9H-carbazole-3-amine was used instead of N-phenylnaphthalene-1-amine. 9.0 g (yield 61%) of the target compound was obtained.

[0340] [LCMS]: 831

[0341] [Synthesis Example 32] Synthesis of Compound 166

[0342]

[0343] The same process as [Synthesis Example 1] was carried out except that 9-bromospiro[benzo[c]fluorene-7,9'-thioxanthene] of Preparation Example 6 was used instead of 9-bromospiro[benzo[c]fluorene-7,9'-xanthene] used in Synthesis Example 1, and N-phenyl-[1,1'-biphenyl]-4-amine was used instead of di([1,1'-biphenyl]-4-yl)amine. 8.8 g (yield 58%) of the target compound was obtained.

[0344] [LCMS]: 641

[0345] [Synthesis Example 33] Synthesis of Compound 171

[0346]

[0347] The 9-bromospiro[benzo[c]fluorene-7,9'-thioxanthene] of Preparation Example 6 was used instead of the 9-bromospiro[benzo[c]fluorene-7,9'-xanthene] used in Synthesis Example 1, and N-([1,1'-biphenyl]-2-yl)-9,9-dimethyl-9H-fluorene-2-amine was used instead of di([1,1'-biphenyl]-4-yl)amine. Except for this, the same process as [Synthesis Example 1] was carried out to obtain 7.2 g (yield 73%) of the target compound.

[0348] [LCMS]: 758

[0349] [Synthesis Example 34] Synthesis of Compound 178

[0350]

[0351] The 9-bromospiro[benzo[c]fluorene-7,9'-thioxanthene] of Preparation Example 6 was used instead of the 9-bromospiro[benzo[c]fluorene-7,9'-xanthene] used in Synthesis Example 1, and N-([1,1'-biphenyl]-4-yl)dibenzo[b,d]furan-2-amine was used instead of di([1,1'-biphenyl]-4-yl)amine. Except for this, the same process as [Synthesis Example 1] was carried out to obtain 5.5 g (yield 67%) of the target compound.

[0352] [LCMS]: 731

[0353] [Synthesis Example 35] Synthesis of Compound 187

[0354]

[0355] The 9-bromospiro[benzo[c]fluorene-7,9'-thioxanthene] of Preparation Example 6 was used instead of the 9-bromospiro[benzo[c]fluorene-7,9'-xanthene] used in Synthesis Example 1, and N-([1,1'-biphenyl]-4-yl)dibenzo[b,d]thiophene-1-amine was used instead of di([1,1'-biphenyl]-4-yl)amine. Except for this, the same process as [Synthesis Example 1] was carried out to obtain 3.9 g of the target compound (yield 60%).

[0356] [LCMS]: 747

[0357] [Synthesis Example 36] Synthesis of Compound 195

[0358]

[0359] The 9-bromospiro[benzo[c]fluorene-7,9'-thioxanthene] of Preparation Example 6 was used instead of the 9-bromospiro[benzo[c]fluorene-7,9'-xanthene] used in Synthesis Example 1, and N-([1,1'-biphenyl]-2-yl)-9-phenyl-9H-carbazole-3-amine was used instead of di([1,1'-biphenyl]-4-yl)amine. Except for this, the same process as [Synthesis Example 1] was carried out to obtain 5.8 g (yield 49%) of the target compound.

[0360] [LCMS]: 807

[0361] [Synthesis Example 37] Synthesis of Compound 199

[0362]

[0363] The 9-bromospiro[benzo[c]fluorene-7,9'-thioxanthene] of Preparation Example 6 was used instead of the 9-bromospiro[benzo[c]fluorene-7,9'-xanthene] used in Synthesis Example 1, and N-(dibenzo[b,d]thiophene-3-yl)dibenzo[b,d]furan-3-amine was used instead of di([1,1'-biphenyl]-4-yl)amine. Except for this, the same process as [Synthesis Example 1] was carried out to obtain 6.1 g (yield 55%) of the target compound.

[0364] [LCMS]: 761

[0365] [Synthesis Example 38] Synthesis of Compound 203

[0366]

[0367] The same process as [Synthesis Example 1] was carried out except that 2-bromospiro[benzo[b]fluorene-11,9'-thioxanthene] of Preparation Example 7 was used instead of 9-bromospiro[benzo[c]fluorene-7,9'-xanthene] used in Synthesis Example 1, and N-([1,1'-biphenyl]-2-yl)-9,9-dimethyl-9H-fluorene-2-amine was used instead of di([1,1'-biphenyl]-4-yl)amine. 9.3 g (yield 62%) of the target compound was obtained.

[0368] [LCMS]: 758

[0369] [Synthesis Example 39] Synthesis of Compound 208

[0370]

[0371] The same process as [Synthesis Example 1] was carried out except that 2-bromospiro[benzo[b]fluorene-11,9'-thioxanthene] of Preparation Example 7 was used instead of 9-bromospiro[benzo[c]fluorene-7,9'-xanthene] used in Synthesis Example 1, and N-(4-(dibenzo[b,d]furan-4-yl)phenyl)-[1,1'-biphenyl]-4-amine was used instead of di([1,1'-biphenyl]-4-yl)amine. 3.3 g (yield 66%) of the target compound was obtained.

[0372] [LCMS]: 808

[0373] [Synthesis Example 40] Synthesis of Compound 216

[0374]

[0375] The same process as [Synthesis Example 1] was carried out except that 2-bromospiro[benzo[b]fluorene-11,9'-thioxanthene] of Preparation Example 7 was used instead of 9-bromospiro[benzo[c]fluorene-7,9'-xanthene] used in Synthesis Example 1, and N-(9,9-dimethyl-9H-fluorene-2-yl)-9-phenyl-9H-carbazole-3-amine was used instead of di([1,1'-biphenyl]-4-yl)amine. 5.5 g (yield 60%) of the target compound was obtained.

[0376] [LCMS]: 847

[0377] [Synthesis Example 41] Synthesis of Compound 218

[0378]

[0379] The same process as in [Synthesis Example 1] was carried out except that 9-bromospiro[benzo[a]fluorene-11,9'-thioxanthene] of Preparation Example 8 was used instead of 9-bromospiro[benzo[c]fluorene-7,9'-xanthene] used in Synthesis Example 1 to obtain 7.2 g (yield 49%) of the target compound.

[0380] [LCMS]: 717

[0381] [Synthesis Example 42] Synthesis of Compound 227

[0382]

[0383] The 9-bromospiro[benzo[a]fluorene-11,9'-thioxanthine] of Preparation Example 8 was used instead of the 9-bromospiro[benzo[c]fluorene-7,9'-xanthene] used in Synthesis Example 1, and N-([1,1'-biphenyl]-2-yl)dibenzo[b,d]thiophene-2-amine was used instead of di([1,1'-biphenyl]-4-yl)amine. Except for this, the same process as [Synthesis Example 1] was carried out to obtain 6.1 g (yield 65%) of the target compound.

[0384] [LCMS]: 747

[0385] [Synthesis Example 43] Synthesis of Compound 229

[0386]

[0387] The 9-bromospiro[benzo[a]fluorene-11,9'-thioxanthene] of Preparation Example 8 was used instead of the 9-bromospiro[benzo[c]fluorene-7,9'-xanthene] used in Synthesis Example 1, and N-([1,1'-biphenyl]-4-yl)-9-phenyl-9H-carbazole-3-amine was used instead of di([1,1'-biphenyl]-4-yl)amine. Except for this, the same process as [Synthesis Example 1] was carried out to obtain 12.1 g (yield 72%) of the target compound.

[0388] [LCMS]: 807

[0389] [Synthesis Example 44] Synthesis of Compound 231

[0390]

[0391] The same process as [Synthesis Example 1] was carried out except that 9-bromospiro[benzo[a]fluorene-11,9'-thioxanthene] of Preparation Example 8 was used instead of 9-bromospiro[benzo[c]fluorene-7,9'-xanthene] used in Synthesis Example 1, and N-(9,9-dimethyl-9H-fluorene-2-yl)-9-phenyl-9H-carbazole-3-amine was used instead of di([1,1'-biphenyl]-4-yl)amine. 9.6 g (yield 66%) of the target compound was obtained.

[0392] [LCMS]: 847

[0393] [Synthesis Example 45] Synthesis of Compound 237

[0394]

[0395] The 11-chlorospiro[benzo[c]fluorene-7,9'-thioxanthene] of Preparation Example 9 was used instead of the 9-bromospiro[benzo[c]fluorene-7,9'-xanthene] used in Synthesis Example 1, and N-([1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-2-amine was used instead of di([1,1'-biphenyl]-4-yl)amine. Except for this, the same process as [Synthesis Example 22] was carried out to obtain 6.0 g (yield 55%) of the target compound.

[0396] [LCMS]: 717

[0397] [Synthesis Example 46] Synthesis of Compound 241

[0398]

[0399] Using 4,4,5,5-tetramethyl-2-(spiro[benzo[c]fluorene-7,9'-thioxanthine]-11-yl)-1,3,2-dioxaborolane used in Synthesis Example 4 instead of 4,4,5,5-tetramethyl-2-(spiro[benzo[c]fluorene-7,9'-xanthene]-9-yl)-1,3,2-dioxaborolane prepared in Preparation Example 13, the same process as in [Synthesis Example 4] was carried out to obtain 8.2 g (yield 49%) of the target compound.

[0400] [LCMS]: 834

[0401] [Synthesis Example 47] Synthesis of Compound 244

[0402]

[0403] The same process as [Synthesis Example 4] was carried out except that 4,4,5,5-tetramethyl-2-(spiro[benzo[c]fluorene-7,9'-thioxanthen]-11-yl)-1,3,2-dioxaborolane of Preparation Example 13 was used instead of 4,4,5,5-tetramethyl-2-(spiro[benzo[c]fluorene-7,9'-xanthene]-9-yl)-1,3,2-dioxaborolane used in Synthesis Example 4, and N-([1,1'-biphenyl]-4-yl)-N-(4-chlorophenyl)dibenzo[b,d]thiophene-2-amine was used instead of N-([1,1'-biphenyl]-4-yl)-N-(4-chlorophenyl)-9,9-dimethyl-9H-fluorene-2-amine. 4.4 g (yield 53%) of the target compound was obtained.

[0404] [LCMS]: 824

[0405] [Synthesis Example 48] Synthesis of Compound 254

[0406]

[0407] The same process as [Synthesis Example 4] was carried out except that 4,4,5,5-tetramethyl-2-(spiro[benzo[c]fluorene-7,9'-thioxanthen]-11-yl)-1,3,2-dioxaborolane of Preparation Example 13 was used instead of 4,4,5,5-tetramethyl-2-(spiro[benzo[c]fluorene-7,9'-xanthene]-9-yl)-1,3,2-dioxaborolane used in Synthesis Example 4, and N-(4-chlorophenyl)-N,9-diphenyl-9H-carbazole-3-amine was used instead of N-([1,1'-biphenyl]-4-yl)-N-(4-chlorophenyl)-9,9-dimethyl-9H-fluorene-2-amine. 9.9 g (yield 63%) of the target compound was obtained.

[0408] [LCMS]: 807

[0409] [Example 1] Preparation of organic electroluminescent element

[0410] The compound 2 synthesized in the above-mentioned Synthesis Example 1 was purified by sublimation to a high purity by a generally known method, and then a green organic electroluminescent device was prepared according to the following process.

[0411] First, we will The glass substrate coated with a thin film of indium tin oxide (ITO) was ultrasonically cleaned with distilled water. After the distilled water washing, it was ultrasonically cleaned with isopropyl alcohol, acetone, methanol and other solvents and dried, and then transferred to a UV OZONE cleaning machine (Power sonic 405, HwashinTech), and then UV cleaned for 5 minutes, and then the coated glass substrate was transferred to a vacuum evaporator.

[0412] On the thus prepared ITO transparent glass substrate (electrode), m-MTDATA (60nm) / Compound 2 (80nm) / DS-H522+5% DS-501 (300nm) / BCP (10nm) / Alq3 (30nm) / LiF (1nm) / Al (200nm) were stacked in this order to produce an organic EL element. The DS-H522 and DS-501 used at this time were products of Doosan Electronics BG, and the structures of m-MTDATA, BCP and Alq3 were as follows.

[0413]

[0414] [Examples 2 to 44] Preparation of organic electroluminescent elements

[0415] Organic electroluminescent devices were prepared in the same manner as in Example 1 except that the compounds listed in the following Table 1 were used instead of Compound 2 used as a hole transport layer material when forming the hole transport layer in Example 1.

[0416] [Comparative Example 1] Preparation of organic electroluminescent element

[0417] An organic EL device was produced in the same manner as in Example 1 except that NPB was used as the hole transport layer material instead of Compound 2 used as the hole transport layer material when the hole transport layer was formed in Example 1. The structure of NPB used in this case is as follows.

[0418]

[0419] [Evaluation Example 1]

[0420] For each of the green organic electroluminescent devices prepared in Examples 1 to 44 and Comparative Example 1, the current density of 10 mA / cm 2 The driving voltage and current efficiency at the time of , are shown in the following Table 1.

[0421] [Table 1]

[0422]

[0423]

[0424] As shown in Table 1 above, it can be seen that the organic electroluminescent element using the compound of the present invention for the hole transport layer (the organic electroluminescent elements manufactured in Examples 1 to 44, respectively) shows excellent performance in current efficiency and driving voltage compared with the case where NBP was used as a hole transport layer material in the past (the organic electroluminescent element of Comparative Example 1).

Claims

1. An organic compound represented by any one of the following chemical formulas 3 to 5: Chemical formula 3 Chemical formula 4 Chemical formula 5 In the chemical formulas 3 to 5, X is O or S, a and b are 4 each, R1 and R2 are the same or different from each other and are each independently hydrogen or deuterium, n1 to n3 are each an integer from 0 to 3, L1 to L3 are the same or different from each other, and L1 is selected from a single bond and C6~C 18 The group consisting of arylene groups, L2 and L3 are each independently selected from a single bond, C6 to C 18 and a heteroarylene group having 5 to 18 atomic nuclei, Ar1 and Ar2 are the same or different from each other and are independently selected from C6 to C 60 A group consisting of an aryl group and a heteroaryl group having 5 to 60 atomic nuclei, The arylene group of L1, the arylene group and heteroarylene group of L2 and L3, and the aryl group and heteroaryl group of Ar1 and Ar2 are each independently selected from hydrogen, deuterium, halogen, cyano, nitro, C1-C 40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 nuclei, C6~C 60 aryl, heteroaryl with 5 to 60 nuclei, C1~C 40 Alkoxy, C6~C 60 Aryloxy, C1~C 40 Alkyl silyl, C6~C 60 Aryl silyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, C6~C 60 Arylphosphine, C6~C 60 The aryl phosphine oxide group and C6~C 60 The arylamine group may be substituted or unsubstituted with one or more substituents. In this case, when there are multiple substituents, they may be the same as or different from each other.

2. The compound according to claim 1, wherein the compound represented by any one of Chemical Formulae 3 to 5 is selected from the group consisting of the following compounds (1) to (259):

3. The compound according to claim 1, wherein the compound represented by any one of Chemical Formulas 3 to 5 is represented by the following Chemical Formula 6 or 7: Chemical formula 6 Chemical formula 7 In the chemical formulas 6 and 7, X, R1, R2, a, b, L1 to L3, n1 to n3, Ar1 are each as defined in claim 1, Ring B is a C6 monocyclic aromatic ring, c is 0 or 1, Y1 is selected from the group consisting of O, S, C(Ar3)(Ar4) and N(Ar5), d is an integer from 0 to 4, e is an integer from 0 to 3, R3, R4, Ar3 to Ar5 are the same or different from each other and are independently selected from hydrogen, deuterium, halogen, cyano, nitro, amino, C1-C 40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 atomic nuclei, C6~C 60 aryl, heteroaryl with 5 to 60 atomic nuclei, C1~C 40 Alkoxy, C6~C 60 Aryloxy, C1~C 40 Alkyl silyl, C6~C 60 Aryl silyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, C6~C 60 Arylphosphine, C6~C 60The aryl phosphine oxide group and C6~C 60 A group consisting of arylamine groups, The monocyclic aromatic ring of the B ring, the alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, alkoxy, aryloxy, alkylsilyl, arylsilyl, alkylboryl, arylboryl, arylphosphino, arylphosphine oxide and arylamine groups of R3, R4, Ar3 to Ar5 are each independently selected from hydrogen, deuterium, halogen, cyano, nitro, C1~C 40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 nuclei, C6~C 60 aryl, heteroaryl with 5 to 60 nuclei, C1~C 40 Alkoxy, C6~C 60 Aryloxy, C1~C 40 Alkyl silyl, C6~C 60 Aryl silyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, C6~C 60 Arylphosphine, C6~C 60 The aryl phosphine oxide group and C6~C 60 The arylamine group may be substituted or unsubstituted with one or more substituents. In this case, when there are multiple substituents, they may be the same as or different from each other.

4. The compound according to claim 1, wherein the compound represented by any one of Chemical Formulas 3 to 5 is represented by any one of the following Chemical Formulas 8 to 13: Chemical formula 8 Chemical formula 9 Chemical formula 10 Chemical formula 11 Chemical formula 12 Chemical formula 13 In the chemical formulas 8 to 13, X, R1, R2, a, b, L2 to L3, n1 to n3, Ar1 are each as defined in claim 1, c is 0 or 1, Y1 is selected from the group consisting of O, S, C(Ar3)(Ar4) and N(Ar5), d is an integer from 0 to 4, e is an integer from 0 to 3, R3, R4, Ar3 to Ar5 are the same or different from each other and are independently selected from hydrogen, deuterium, halogen, cyano, nitro, amino, C1-C 40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 atomic nuclei, C6~C 60 aryl, heteroaryl with 5 to 60 atomic nuclei, C1~C 40 Alkoxy, C6~C 60 Aryloxy, C1~C 40 Alkyl silyl, C6~C 60 Aryl silyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, C6~C 60 Arylphosphine, C6~C 60 The aryl phosphine oxide group and C6~C 60 A group consisting of arylamine groups, The alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, alkoxy, aryloxy, alkylsilyl, arylsilyl, alkylboryl, arylboryl, arylphosphino, arylphosphine oxide and arylamine groups of R3, R4, Ar3 to Ar5 are each independently selected from hydrogen, deuterium, halogen, cyano, nitro, C1~C 40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 nuclei, C6~C 60 aryl, heteroaryl with 5 to 60 nuclei, C1~C 40 Alkoxy, C6~C 60 Aryloxy, C1~C 40 Alkyl silyl, C6~C 60 Aryl silyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, C6~C 60 Arylphosphine, C6~C 60 The aryl phosphine oxide group and C6~C 60 The arylamine group may be substituted or unsubstituted with one or more substituents. In this case, when there are multiple substituents, they may be the same as or different from each other.

5. The compound according to claim 1, wherein the compound represented by any one of Chemical Formulas 3 to 5 is represented by any one of the following Chemical Formulas 14 to 22: Chemical formula 14 Chemical formula 15 Chemical formula 16 Chemical formula 17 Chemical formula 18 Chemical formula 19 Chemical formula 20 Chemical formula 21 Chemical formula 22 In the chemical formulas 14 to 22, X, R1, R2, a, b, n1 to n3 are each the same as defined in claim 1, c and f are 0 or 1 respectively, Y1 is selected from the group consisting of O, S, C(Ar3)(Ar4) and N(Ar5), Y2 is the same as or different from Y1 and is selected from the group consisting of O, S, C(Ar6)(Ar7) and N(Ar8), d and g are each an integer from 0 to 4, e and h are each an integer from 0 to 3, R3 to R6 and Ar3 to Ar8 are the same as or different from each other and are independently selected from hydrogen, deuterium, halogen, cyano, nitro, amino, C1-C 40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 atomic nuclei, C6~C 60 aryl, heteroaryl with 5 to 60 atomic nuclei, C1~C 40 Alkoxy, C6~C 60 Aryloxy, C1~C 40 Alkyl silyl, C6~C 60 Aryl silyl, C1~C40 Alkyl boron, C6~C 60 Aryl boron, C6~C 60 Arylphosphine, C6~C 60 The aryl phosphine oxide group and C6~C 60 A group consisting of arylamine groups, The alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, alkoxy, aryloxy, alkylsilyl, arylsilyl, alkylboryl, arylboryl, arylphosphino, arylphosphine oxide and arylamine groups of R3 to R6 and Ar3 to Ar8 are each independently selected from hydrogen, deuterium, halogen, cyano, nitro, C1~C 40 Alkyl, C2~C 40 Alkenyl, C2~C 40 Alkynyl, C3~C 40 Cycloalkyl, heterocycloalkyl with 3 to 40 nuclei, C6~C 60 aryl, heteroaryl with 5 to 60 nuclei, C1~C 40 Alkoxy, C6~C 60 Aryloxy, C1~C 40 Alkyl silyl, C6~C 60 Aryl silyl, C1~C 40 Alkyl boron, C6~C 60 Aryl boron, C6~C 60 Arylphosphine, C6~C 60 The aryl phosphine oxide group and C6~C 60 The arylamine group may be substituted or unsubstituted with one or more substituents. In this case, when there are multiple substituents, they may be the same as or different from each other.

6. An organic electroluminescent element comprising (i) an anode, (ii) a cathode, and (iii) one or more organic layers between the anode and the cathode, At least one of the one or more organic layers comprises the organic compound according to any one of claims 1 to 5. 7 . The organic electroluminescent element according to claim 6 , wherein the organic layer containing the organic compound is a hole transport layer.

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