Organic electroluminescent compounds and organic electroluminescent devices containing the same

Abstract

To provide an organic electroluminescent compound, and an organic electroluminescent device including the same.SOLUTION: The present disclosure relates to an organic electroluminescent compound and an organic electroluminescent device including the same. By including the organic electroluminescent compound according to the present disclosure, it is possible to provide organic electroluminescent devices having lower driving voltages and / or higher efficiency characteristics compared to conventional organic electroluminescent devices.SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present disclosure relates to organic electroluminescent compounds and organic electroluminescent devices containing the same. [Background technology]

[0002] A green-emitting TPD / Alq3 bilayer small molecule organic electroluminescent device (OLED), consisting of an emissive layer and a charge transport layer, was first developed by Tang et al. at Eastman Kodak in 1987. Since then, research on OLEDs has progressed rapidly, and OLEDs have been commercialized. Currently, organic electroluminescent devices mainly use phosphorescent materials with excellent luminous efficiency in panel implementation. Therefore, OLEDs with high luminous efficiency are needed for long-term use and high display resolution.

[0003] Patent Documents 1 and 2 disclose dihydrophenanthrene derivatives as hole transport materials. However, these references do not disclose organic electroluminescent compounds having improved performance, such as low driving voltage and / or high efficiency, by including dihydrophenanthrene compounds having specific substituents as organic electroluminescent materials as described in the present disclosure. [Prior art documents] [Patent documents]

[0004] [Patent Document 1] US Patent No. 8,129,037 B2 [Patent Document 2] Chinese Patent No. 110105225 B Specification [Patent Document 3] Korean Patent Application Publication No. 10-2020-0092879 Summary of the Invention [Problem to be solved by the invention]

[0005] The object of the present disclosure is, first, to provide an organic electroluminescent compound that is effective for producing an organic electroluminescent device having low driving voltage and / or high efficiency characteristics, and, second, to provide an organic electroluminescent device comprising the organic electroluminescent compound according to the present disclosure. [Means for solving the problem]

[0006] As a result of intensive research to solve above technical problems, the present inventors have found that the above-mentioned object can be achieved by the organic electroluminescent compound represented by the following formula 1 and the organic electroluminescent device comprising the same, thereby completing the present invention: [ka]

[0007] In Equation 1, Ring A and ring B are each independently substituted or unsubstituted (C6 to C 30 ) arene, or substituted or unsubstituted (3- to 30-membered) heteroarene; R1~R4, R a , and R b are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C 30 ) alkyl, substituted or unsubstituted (C6-C 30 ) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, substituted or unsubstituted (C3-C 30 ) cycloalkyl, substituted or unsubstituted (C1-C 30 ) alkoxy, substituted or unsubstituted tri(C1-C 30 ) alkylsilyl, substituted or unsubstituted di(C1-C 30 ) Alkyl (C6-C 30 ) arylsilyl, substituted or unsubstituted (C1-C 30 ) Alkyldi(C6~C 30 ) arylsilyl, substituted or unsubstituted tri(C6-C30 ) Arylsilyl, (C3-C 30 ) aliphatic ring and (C6~C 30 ) substituted or unsubstituted fused rings with aromatic rings, substituted or unsubstituted mono- or di-(C1-C 30 ) alkylamino, substituted or unsubstituted mono- or di(C6-C 30 ) arylamino, substituted or unsubstituted (C1-C 30 ) Alkyl (C6-C 30 )arylamino, substituted or unsubstituted mono- or di(3-30 membered)heteroarylamino, or substituted or unsubstituted (C6-C 30 ) aryl(3-30 membered)heteroarylamino; or it may combine with adjacent substituents to form a ring; However, R1 to R4, R a , and R b At least one of the following is represented by Formula 1-1: [ka] In Formula 1-1, L1 to L3 each independently represent a single bond, a substituted or unsubstituted (C6 to C 30 ) arylene, or substituted or unsubstituted (3 to 30 membered) heteroarylene; Ar1 and Ar2 are each independently a substituted or unsubstituted (C6 to C 30 )aryl, substituted or unsubstituted (3-30 membered)heteroaryl, or substituted or unsubstituted (C3-C 30 ) represents cycloalkyl; provided that at least one of Ar1 and Ar2 is a substituted or unsubstituted (C3-C30)cycloalkyl; n and m are integers of 1 to 8, and when n and m are integers of 2 or more, R a and R b may be the same or different.

[0008] Advantageous Effects of the Invention By including the organic electroluminescent compound according to the present disclosure, an organic electroluminescent device having low driving voltage and / or high efficiency characteristics can be provided. DETAILED DESCRIPTION OF THE INVENTION

[0009] The present disclosure will be described in detail hereinafter. However, the following description is intended to illustrate the present invention and is not meant to limit the scope of the present invention in any way.

[0010] The present disclosure relates to an organic electroluminescent compound represented by Formula 1, and an organic electroluminescent device comprising the organic electroluminescent compound.

[0011] The term "organic electroluminescent compound" in the present disclosure means a compound that can be used in an organic electroluminescent device and, if necessary, can be included in any material layer that constitutes the organic electroluminescent device.

[0012] In this specification, the term "organic electroluminescent material" refers to a material that can be used in an organic electroluminescent device and can include at least one compound.The organic electroluminescent material can be included in any layer that constitutes an organic electroluminescent device, as needed.For example, the organic electroluminescent material can be a hole injection material, a hole transport material, a hole auxiliary material, a light-emitting auxiliary material, an electron blocking material, a light-emitting material (including a host and a dopant material), an electron buffer material, a hole blocking material, an electron transport material, or an electron injection material, etc.

[0013] In this specification, "(C1 to C 30The term "(C3-C ) alkyl" means a straight-chain or branched alkyl having 1 to 30 carbon atoms constituting the chain, where the number of carbon atoms is preferably 1 to 20, more preferably 1 to 10. The alkyl may include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, etc. In the present specification, the term "(C3-C 30"Cycloalkyl" refers to a monocyclic or polycyclic saturated or partially unsaturated cyclic hydrocarbon substituent having 3 to 30 ring skeletal carbon atoms, preferably 3 to 20, more preferably 3 to 7. Non-limiting examples of monocyclic cycloalkyls include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclohexenyl, cyclohexadienyl, cycloheptyl, cycloheptatrienyl, and cyclooctyl. Polycyclic cycloalkyls include spirocyclic, fused-ring, and bridged-ring cycloalkyls. The cycloalkyl rings can be fused to aryl, heteroaryl, or heterocycloalkyl rings, and non-limiting examples of cycloalkyl rings include indanyl, tetrahydronaphthalenyl, benzocycloheptenyl, and the like. Bridged-ring cycloalkyl refers to a 5- to 20-membered, preferably 6- to 14-membered, more preferably 7- to 10-membered all-carbon polycyclic group having two rings sharing two unbonded carbon atoms, which may contain one or more double bonds, but neither ring has a fully conjugated π-electron system. Depending on the number of rings formed, it can be classified as a bicyclic, tricyclic, tetracyclic, or polycyclic bridged cycloalkyl, preferably bicyclic, tricyclic, or tetracyclic, more preferably bicyclic or tricyclic. Bridged-ring cycloalkyls include, for example, adamantanyl, norbornanyl, norbornenyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, bicyclo[2.2.1]heptanyl, bicyclo[2.2.2]octyl, and the like. As used herein, "(3- to 20-membered)heterocycloalkyl" refers to a saturated or partially unsaturated monocyclic or polycyclic hydrocarbon substituent having a ring skeleton of 3 to 20 atoms, wherein the number of carbon atoms is 3 to 7, preferably 5 to 7, and the heterocycloalkyl contains at least one heteroatom selected from the group consisting of B, N, O, S, Si, and P, preferably the group consisting of O, S, and N. For example, the heterocycloalkyl includes tetrahydrofuran, pyrrolidine, thiolane, tetrahydropyran, etc. As used herein, "(C6-C 30"Aryl(ene)" means a monocyclic or fused ring system radical derived from an aromatic hydrocarbon having 6 to 30 ring skeletal carbon atoms, which may be partially saturated, and may contain a spiro structure. The number of carbon atoms in the ring skeleton is preferably 6 to 20, more preferably 6 to 15. Specific examples of aryl include phenyl, biphenyl, terphenyl, quaterphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl, dimethylfluorenyl, diphenylfluorenyl, benzofluorenyl, diphenylbenzofluorenyl, dibenzofluorenyl, phenanthrenyl, benzophenanthrenyl, phenylphenanthrenyl, anthracenyl, benzanthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, chrysenyl, benzochrysenyl, naphthacenyl, fluoranthenyl, benzofluoranthenyl, tolyl, xylyl, mesityl, cumenyl, spiro[fluorene-fluorenyl]yl (spirobifluorenyl), spiro[fluorene-benzofluorenyl]yl, azulenyl, and the like. More specifically, aryl is o-tolyl, m-tolyl, p-tolyl, 2,3-xylyl, 3,4-xylyl, 2,5-xylyl, mesityl, o-cumenyl, m-cumenyl, p-cumenyl, p-pt-butylphenyl, p-(2-phenylpropyl)phenyl, 4'-methylbiphenyl, 4"-t-butyl-p-terphenyl-4-yl, o-biphenyl, m-biphenyl, p-biphenyl, o-terphenyl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, p-terphenyl-4-yl, p-terphenyl-3-yl, p- terphenyl-2-yl, m-quaterphenyl, 1-naphthyl, 2-naphthyl, 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, 9-fluorenyl, 9,9-dimethyl-1-fluorenyl, 9,9-dimethyl-2-fluorenyl, 9,9-dimethyl-3-fluorenyl, 9,9-dimethyl-4-fluorenyl, 9,9-diphenyl-1-fluorenyl, 9,9-diphenyl-2-fluorenyl, 9,9-diphenyl-3-fluorenyl, 9,9-diphenyl-4-fluorenyl, 1-anthryl, 2-anthryl, 9-anthryl,The heteroaryl group may be 1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl, 9-phenanthryl, 1-chrysenyl, 2-chrysenyl, 3-chrysenyl, 4-chrysenyl, 5-chrysenyl, 6-chrysenyl, benzo[c]phenanthryl, benzo[g]chrysenyl, 1-triphenylenyl, 2-triphenylenyl, 3-triphenylenyl, 4-triphenylenyl, 3-fluoranthenyl, 4-fluoranthenyl, 8-fluoranthenyl, 9-fluoranthenyl, or benzofluoranthenyl. As used herein, the term "(3- to 30-membered)heteroaryl(ene)" refers to an aryl group having 3 to 30 skeletal ring atoms and containing at least one heteroatom selected from the group consisting of N, O, S, Si, P, Se, and Ge, and preferably has 5 to 25 skeletal ring atoms. The number of heteroatoms is preferably 1 to 4, and the heteroaryl (ene) may be a monocyclic ring system or a fused ring system fused with one or more benzene rings, and may be partially saturated. Furthermore, the heteroaryl herein may be formed by bonding at least one heteroaryl group or aryl group to a heteroaryl group via a single bond. Specific examples of heteroaryl include monocyclic ring heteroaryls including furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyridinyl, pyrimidinyl, and pyridazinyl, as well as benzofuranyl, benzothiophenyl, isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl, benzophenone, and benzophenone. benzoimidazolyl, benzothiazolyl, benzisothiazolyl, benzisoxazolyl, benzoxazolyl, imidazopyridinyl, isoindolyl, indolyl, benzoindolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolyl, quinazolinyl, quinoxalinyl, carbazolyl, azacarbazolyl, benzocarbazolyl, dibenzocarbazolyl, phenoxazinyl, phenanthridinyl, benzodioxolyl, indolizidinyl, acridinyl, silafluorenyl,It can be a fused ring system heteroaryl, including germafluorenyl, etc. More specifically, the heteroaryl can be 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 6-pyrimidinyl, 1,2,3-triazin-4-yl, 1,2,4-triazin-3-yl, 1,3,5-triazin-2-yl, 1-imidazolyl, 2-imidazolyl, 1-pyrazolyl, 1-indolizidinyl, 2-indolizidinyl, 3-indolizidinyl, 5-indolizidinyl, 6-indolizidinyl, 7-indolizidinyl, 8-Indolizidinyl, 2-Imidazopyridinyl, 3-Imidazopyridinyl, 5-Imidazopyridinyl, 6-Imidazopyridinyl, 7-Imidazopyridinyl, 8-Imidazopyridinyl, 1-Indolyl, 2-Indolyl, 3-Indolyl, 4-Indolyl, 5-Indolyl, 6-Indolyl, 7-Indolyl, 1-Isoindolyl, 2-Isoindolyl, 3-Isoindolyl, 4-Isoindolyl, 5-Isoindolyl, 6-Isoindolyl, 7-Isoindolyl, 2-Furyl, 3-Furyl, 2-Benzofuranyl, 3-Benzofuranyl, 4 -Benzofuranyl, 5-benzofuranyl, 6-benzofuranyl, 7-benzofuranyl, 1-isobenzofuranyl, 3-isobenzofuranyl, 4-isobenzofuranyl, 5-isobenzofuranyl, 6-isobenzofuranyl, 7-isobenzofuranyl, 2-quinolyl, 3-quinolyl, 4-quinolyl, 5-quinolyl, 6-quinolyl, 7-quinolyl, 8-quinolyl, 1-isoquinolyl, 3-isoquinolyl, 4-isoquinolyl, 5-isoquinolyl, 6-isoquinolyl, 7-isoquinolyl, 8-isoquinolyl, 2-quinoxalinyl, 5-quinoxalinyl , 6-quinoxalinyl, 1-carbazolyl, 2-carbazolyl, 3-carbazolyl, 4-carbazolyl, 9-carbazolyl, azacarbazolyl-1-yl, azacarbazolyl-2-yl, azacarbazolyl-3-yl, azacarbazolyl-4-yl, azacarbazolyl-5-yl, azacarbazolyl-6-yl, azacarbazolyl-7-yl, azacarbazolyl-8-yl, azacarbazolyl-9-yl, 1-phenanthridinyl, 2-phenanthridinyl, 3-phenanthridinyl, 4-phenanthridinyl, 6-phenanthridinyl,7-Phenanthridinyl, 8-Phenanthridinyl, 9-Phenanthridinyl, 10-Phenanthridinyl, 1-Acridinyl, 2-Acridinyl, 3-Acridinyl, 4-Acridinyl, 9-Acridinyl, 2-Oxazolyl, 4-Oxazolyl, 5-Oxazolyl, 2-Oxadiazolyl, 5-Oxadiazolyl, 3-Furazanyl, 2-Thienyl, 3-Thienyl, 2-Methylpyrrol-1-yl, 2-Methylpyrrol-3-yl, 2-Methylpyrrol-4-yl, 2-Methylpyrrol-5-yl, 3-Methylpyrrol-1-yl, 3-Methylpyrrol-2-yl, 3-Methylpyrrol-4-yl, 3-Methylpyrrol-5-yl, 2-t-Butylpyrrol-4-yl, 3-(2-phenylpropyl)pyrrol-1-yl, 2-Methyl-1-indolyl, 4-Methyl-1- Indolyl, 2-methyl-3-indolyl, 4-methyl-3-indolyl, 2-t-butyl-1-indolyl, 4-t-butyl-1-indolyl, 2-t-butyl-3-indolyl, 4-t-butyl-3-indolyl, 1-dibenzofuranyl, 2-dibenzofuranyl, 3-dibenzofuranyl, 4-dibenzofuranyl, 1-dibenzothiophenyl, 2-dibenzothiophenyl, 3-dibenzothiophenyl, 4-dibenzothiophenyl, 1-silafluorenyl, 2-silafluorenyl, 3-silafluorenyl, 4-silafluorenyl, 1-germafluorenyl, 2-germafluorenyl, 3-germafluorenyl, 4-germafluorenyl, 1-dibenzoselenophenyl, 2-dibenzoselenophenyl, 3-dibenzoselenophenyl, 4-dibenzoselenophenyl, and the like. Furthermore, "heteroaryl(ene)" can be classified into heteroaryl(ene)s with electronic properties and heteroaryl(ene)s with hole properties. Heteroaryl(ene)s with electronic properties are electron-rich substituents compared to the parent nucleus, for example, they can be substituted or unsubstituted pyridinyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted quinolyl, etc. Heteroaryl(ene)s with hole properties are electron-deficient substituents compared to the parent nucleus, for example, they can be substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzoyl, As used herein, the term "(C3-C6)" refers to a substituted or unsubstituted dibenzothiophenyl. 30 ) aliphatic ring and (C6~C 30 The term "fused ring with an aromatic ring" refers to a ring functional group formed by fusing at least one aliphatic ring having 3 to 30, preferably 3 to 25, and more preferably 3 to 18 ring skeletal carbon atoms with at least one aromatic ring having 6 to 30, preferably 6 to 25, and more preferably 6 to 18 ring skeletal carbon atoms. For example, the fused ring may be a fused ring of at least one benzene and at least one cyclohexane, or a fused ring of at least one naphthalene and at least one cyclopentane, etc. As used herein, a carbon atom in the fused ring of a (C3-C30) aliphatic ring and a (C6-C30) aromatic ring may be replaced with at least one heteroatom selected from B, N, O, S, Si, and P, preferably at least one heteroatom selected from N, O, and S. The term "halogen" in the present disclosure includes F, Cl, Br, and I.

[0014] Additionally, "ortho (o-)," "meta (m-)," and "para (p-)" are meant to indicate the substitution positions of all substituents. The "ortho" configuration refers to a compound having substituents adjacent to each other, for example, at the 1- and 2-positions of a benzene. The "meta" configuration refers to a compound having substituents at the substitution positions next to the immediately adjacent substitution positions, for example, at the 1- and 3-positions of a benzene. The "para" configuration refers to a compound having substituents at the substitution positions next from the meta position, for example, at the 1- and 4-positions of a benzene.

[0015] As used herein, the term "ring formed by bonding adjacent substituents" refers to a substituted or unsubstituted (3- to 30-membered) monocyclic or polycyclic, alicyclic ring, aromatic ring, or combination thereof formed by bonding or condensing two or more adjacent substituents, and preferably a substituted or unsubstituted (3- to 26-membered) monocyclic or polycyclic, alicyclic ring, aromatic ring, or combination thereof. Furthermore, the formed ring may contain at least one heteroatom selected from the group consisting of B, N, O, S, Si, and P, preferably N, O, and S. According to one embodiment of the present disclosure, the number of atoms in the ring skeleton is 5 to 20, and according to another embodiment of the present disclosure, the number of atoms in the ring skeleton is 5 to 15.

[0016] In addition, the term "substituted" in the expression "substituted or unsubstituted" means that a hydrogen atom in a specific functional group is replaced with another atom or functional group, i.e., a substituent. Unless otherwise specified, a substituent can replace a hydrogen atom at any position where the substituent can replace without limitation, and when two or more hydrogen atoms in a functional group are each replaced with a substituent, each substituent can be the same or different. The maximum number of substituents that can be substituted for a certain functional group can be the total number of valences that can be substituted for each atom forming the functional group. In the formulae of the present disclosure, substituted arene, substituted heteroarene, substituted alkyl, substituted aryl(ene), substituted heteroaryl(ene), substituted cycloalkyl, substituted alkoxy, substituted trialkylsilyl, substituted dialkylarylsilyl, substituted alkyldiarylsilyl, substituted triarylsilyl, substituted fused ring of an aliphatic ring and an aromatic ring, substituted mono- or dialkylamino, substituted mono- or diarylamino, substituted alkylarylamino, substituted mono- or diheteroarylamino, and substituted arylheteroarylamino each independently represent deuterium; halogen; cyano; carboxyl; nitro; hydroxy; (C1-C 30 ) alkyl; halo(C1-C 30 ) alkyl; (C2-C 30 ) alkenyl; (C2-C 30 ) alkynyl; (C1-C 30)Alkoxy; (C1-C 30 ) Alkylthio; (C3-C 30 ) cycloalkyl; (C3-C 30 ) cycloalkenyl; (3-7 membered) heterocycloalkyl; (C6-C 30 )aryloxy;(C6-C 30 ) arylthio; unsubstituted or (C6-C 30 ) aryl-substituted (5-30 membered) heteroaryl; unsubstituted or (5-30 membered) heteroaryl-substituted (C6-C 30 ) aryl; tri(C1-C 30 ) alkylsilyl; tri(C6-C 30 ) arylsilyl; di(C1-C 30 ) Alkyl (C6-C 30 ) arylsilyl; (C1-C 30 ) Alkyldi(C6~C 30 ) arylsilyl; (C3-C 30 ) aliphatic ring and (C6~C 30 ) fused ring with aromatic ring; amino; mono- or di(C1-C 30 ) alkylamino; substituted or unsubstituted mono- or di(C6-C 30 ) arylamino; (C1-C 30 ) Alkyl (C6-C 30 )arylamino;mono- or di(3-30 membered)heteroarylamino;(C1-C 30 ) alkyl(3-30 membered)heteroarylamino; (C6-C 30 ) aryl(3-30 membered)heteroarylamino; (C1-C 30 ) alkylcarbonyl; (C1-C 30 ) alkoxycarbonyl; (C6-C 30 ) arylcarbonyl; (C6-C 30 ) arylphosphinyl, di(C6-C 30 )arylboronyl;di(C1-C 30 ) alkylboronyl; (C1-C 30 ) Alkyl (C6-C 30 ) arylboronyl; (C6-C 30 ) Al (C1~C 30 ) alkyl; (C1-C30 ) Alkyl (C6-C 30 ) aryl, and combinations thereof. For example, the substituents may be substituted or unsubstituted methyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted diphenylfluorenyl, substituted or unsubstituted dimethylfluorenyl, substituted or unsubstituted pyridinyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, or substituted or unsubstituted carbazolyl.

[0017] In this specification, if a substituent is not shown in a formula or compound structure, it may mean that all positions that can be substituted are hydrogen or deuterium. That is, some hydrogen atoms may be deuterium, an isotope of hydrogen, where the deuterium content may be 0% to 100%. In this specification, if a substituent is not shown in a formula or compound structure, hydrogen and deuterium may coexist in the compound unless deuterium is explicitly excluded, such as when the deuterium content is 0%, the hydrogen content is 100%, or all substituents are specified as hydrogen. Hydrogen-2 may be represented as hydrogen, and its element symbol may also be D or 2 Deuterium, which may be represented as H, is an isotope of hydrogen and has a deuteron, consisting of one proton and one neutron, as its nucleus. Isotopes, meaning atoms with the same atomic number (Z) but different mass numbers (A), can also be interpreted as elements with the same number of protons but different numbers of neutrons.

[0018] As used herein, "combinations thereof" refers to the combination of one or more elements from the corresponding list to form a known or chemically stable configuration that one skilled in the art can envision from the corresponding list. For example, alkyl and deuterium can be combined to form a partially or fully deuterated alkyl group, halogen and alkyl can be combined to form a halogenated alkyl substituent, and halogen, alkyl and aryl can be combined to form a halogenated arylalkyl. For example, preferred combinations of substituents include up to 50 atoms other than hydrogen or deuterium, or up to 40 atoms other than hydrogen or deuterium, or up to 30 atoms other than hydrogen or deuterium. Alternatively, in many cases, preferred combinations of substituents may contain up to 20 atoms other than hydrogen or deuterium.

[0019] In the formulae of the present disclosure, when there are multiple substituents represented by the same symbol, each of the substituents represented by the same symbol may be the same or different.

[0020] Hereinafter, an organic electroluminescent compound according to one embodiment will be described.

[0021] The compound according to one embodiment is represented by Formula 1: [ka]

[0022] In Equation 1, Ring A and ring B are each independently substituted or unsubstituted (C6 to C 30 ) arene, or substituted or unsubstituted (3- to 30-membered) heteroarene; R1~R4, R a , and R b are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C 30 ) alkyl, substituted or unsubstituted (C6-C 30 ) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, substituted or unsubstituted (C3-C30 ) cycloalkyl, substituted or unsubstituted (C1-C 30 ) alkoxy, substituted or unsubstituted tri(C1-C 30 ) alkylsilyl, substituted or unsubstituted di(C1-C 30 ) Alkyl (C6-C 30 ) arylsilyl, substituted or unsubstituted (C1-C 30 ) Alkyldi(C6~C 30 ) arylsilyl, substituted or unsubstituted tri(C6-C 30 ) Arylsilyl, (C3-C 30 ) aliphatic ring and (C6~C 30 ) substituted or unsubstituted fused rings with aromatic rings, substituted or unsubstituted mono- or di-(C1-C 30 ) alkylamino, substituted or unsubstituted mono- or di(C6-C 30 ) arylamino, substituted or unsubstituted (C1-C 30 ) Alkyl (C6-C 30 )arylamino, substituted or unsubstituted mono- or di(3-30 membered)heteroarylamino, or substituted or unsubstituted (C6-C 30 ) aryl(3-30 membered)heteroarylamino; or it may be combined with adjacent substituents to form a ring; However, R1 to R4, R a , and R b is represented by the following formula 1-1: [ka] In Formula 1-1, L1 to L3 each independently represent a single bond, a substituted or unsubstituted (C6 to C 30 ) arylene, or substituted or unsubstituted (3 to 30 membered) heteroarylene; Ar1 and Ar2 are each independently a substituted or unsubstituted (C6 to C 30 )aryl, substituted or unsubstituted (3-30 membered)heteroaryl, or substituted or unsubstituted (C3-C 30 ) represents cycloalkyl; However, at least one of Ar1 and Ar2 is substituted or unsubstituted (C3 to C 30 ) cycloalkyl; n and m are integers of 1 to 8, and when n and m are integers of 2 or more, R a and R b may be the same or different.

[0023] In one embodiment, ring A and ring B are each independently substituted or unsubstituted (C6-C 30 ) arenes, or substituted or unsubstituted (3- to 30-membered) heteroarenes. For example, ring A and ring B may each independently be a benzene ring, a naphthalene ring, a phenanthrene ring, a dibenzothiophene ring, a dibenzofuran ring, a carbazole ring, or a fluorene ring.

[0024] In one embodiment, R1-R4 are each independently hydrogen, deuterium, substituted or unsubstituted (C1-C 30 ) alkyl, substituted or unsubstituted (C6-C 30 )aryl, substituted or unsubstituted (3-30 membered)heteroaryl, or substituted or unsubstituted (C3-C 30 ) cycloalkyl, preferably hydrogen, deuterium, or substituted or unsubstituted (C1-C 10 ) alkyl, more preferably hydrogen, or substituted or unsubstituted (C1-C4) alkyl. For example, R1 to R4 can each independently be hydrogen or substituted or unsubstituted methyl.

[0025] In one embodiment, R a , and R b are each independently hydrogen, deuterium, substituted or unsubstituted (C6 to C 30 ) aryl, substituted or unsubstituted (C5-C 30 ) cycloalkyl, substituted or unsubstituted mono- or di(C1-C 30 ) alkylamino, substituted or unsubstituted mono- or di(C6-C 30 ) arylamino, substituted or unsubstituted (C1-C 30 ) Alkyl (C6-C30 )arylamino, substituted or unsubstituted mono- or di(5-30 membered)heteroarylamino, substituted or unsubstituted (C6-C 30 )aryl (5-30 membered)heteroarylamino, or may be combined with adjacent substituents to form a substituted or unsubstituted (5-30 membered) monocyclic or polycyclic aromatic ring, preferably hydrogen, deuterium, substituted or unsubstituted (C6-C 25 ) aryl, substituted or unsubstituted (C5-C 30 ) cycloalkyl, substituted or unsubstituted mono- or di(C6-C 30 )arylamino, substituted or unsubstituted mono- or di(5-30 membered)heteroarylamino, substituted or unsubstituted (C6-C 30 )aryl (5-30 membered)heteroarylamino, or may be combined with adjacent substituents to form a substituted or unsubstituted (5-25 membered) monocyclic or polycyclic aromatic ring, more preferably hydrogen, substituted or unsubstituted (C6-C 18 ) aryl, substituted or unsubstituted (C5-C 10 ) cycloalkyl, substituted or unsubstituted di(C6-C 30 )arylamino, substituted or unsubstituted di(5-30 membered)heteroarylamino, substituted or unsubstituted (C6-C 30 ) aryl (5-30 membered) heteroarylamino, or may be joined with adjacent substituents to form a substituted or unsubstituted (5-18 membered) monocyclic or polycyclic aromatic ring. For example, R a and R bare each independently hydrogen or a substituted or unsubstituted phenyl, substituted or unsubstituted p-biphenyl, substituted or unsubstituted m-biphenyl, substituted or unsubstituted o-biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted adamantanyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted phenanthrenyl; or a substituted or unsubstituted benzene ring, a substituted or unsubstituted naphthalene ring, a substituted or unsubstituted 1,2,3,4-tetrahydronaphthalene ring, a substituted or unsubstituted benzofuran ring, a substituted or unsubstituted benzothiophene ring, a substituted or unsubstituted indole ring, or a substituted or unsubstituted indene ring bonded to adjacent substituents.

[0026] In one embodiment, R a , and R b At least one of the following may be represented by Formula 1-1:

[0027] In one embodiment, L1, L2, and L3 are each independently a single bond, a substituted or unsubstituted (C6-C 30 ) arylene, or substituted or unsubstituted (5-30 membered) heteroarylene, preferably a single bond, substituted or unsubstituted (C6-C 25 ) arylene, or substituted or unsubstituted (5-25 membered) heteroarylene, more preferably a single bond, substituted or unsubstituted (C6-C 18 ) arylene, or substituted or unsubstituted (5- to 18-membered) heteroarylene. For example, L1 can be substituted or unsubstituted phenylene, substituted or unsubstituted p-biphenylene, substituted or unsubstituted m-biphenylene, substituted or unsubstituted o-biphenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted dibenzofuranylene, substituted or unsubstituted dibenzothiophenylene, substituted or unsubstituted dimethylfluorenylene, or substituted or unsubstituted carbazolylene, and L2 and L3 can each independently be substituted or unsubstituted phenylene or substituted or unsubstituted biphenylene.

[0028] In one embodiment, Ar1 and Ar2 are each independently substituted or unsubstituted (C6-C 30 )aryl, substituted or unsubstituted (5-30 membered)heteroaryl, or substituted or unsubstituted (C3-C 30 ) cycloalkyl, preferably substituted or unsubstituted (C6-C 25 )aryl, substituted or unsubstituted (5-25 membered)heteroaryl, or substituted or unsubstituted (C5-C 30 ) cycloalkyl, more preferably substituted or unsubstituted (C6-C 25 )aryl, substituted or unsubstituted (5-18 membered)heteroaryl, or substituted or unsubstituted (C5-C 30 For example, Ar1 and Ar2 can each independently be substituted or unsubstituted phenyl, substituted or unsubstituted p-biphenyl, substituted or unsubstituted m-biphenyl, substituted or unsubstituted o-biphenyl, substituted or unsubstituted m-terphenyl, substituted or unsubstituted o-terphenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted dimethylfluorenyl, substituted or unsubstituted diethylfluorenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted cycloheptyl, substituted or unsubstituted cyclooctyl, substituted or unsubstituted biphenyl, substituted or unsubstituted phenyl, substituted or unsubstituted p-biphenyl, substituted or unsubstituted m-biphenyl, substituted or unsubstituted o-biphenyl, substituted or unsubstituted m-terphenyl, substituted or unsubstituted o-terphenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted dimethylfluorenyl, substituted or unsubstituted diethylfluorenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted cycloheptyl, substituted or unsubstituted cyclooctyl ... It may be cyclo[1.1.1]pentyl, substituted or unsubstituted bicyclo[2.1.1]hexyl, substituted or unsubstituted bicyclo[2.2.1]heptyl, substituted or unsubstituted bicyclo[3.1.1]heptyl, substituted or unsubstituted bicyclo[2.2.2]octyl, substituted or unsubstituted bicyclo[3.2.1]octyl, substituted or unsubstituted adamantanyl, substituted or unsubstituted 2,3-dihydro-1H-indenyl, substituted or unsubstituted 1,2,3,4-tetrahydronaphthalenyl, substituted or unsubstituted 6,7,8,9-tetrahydro-5H-benzo[7]annulenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, or substituted or unsubstituted carbazolyl.

[0029] In one embodiment, both Ar1 and Ar2 are substituted or unsubstituted (C3-C 30 ) cycloalkyl.

[0030] In one embodiment, at least one of Ar1 and Ar2 can be cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, bicyclo[2.1.1]hexyl, bicyclo[2.2.1]heptyl, bicyclo[3.1.1]heptyl, bicyclo[2.2.2]octyl, bicyclo[3.2.1]octyl, adamantanyl, 2,3-dihydro-1H-indenyl, 1,2,3,4-tetrahydronaphthalenyl, or 6,7,8,9-tetrahydro-5H-benzo[7]annulenyl.

[0031] In one embodiment, the organic electroluminescent compound according to Formula 1 can be substituted with at least one deuterium.

[0032] According to one embodiment, the organic electroluminescent compound represented by formula 1 can have a refractive index of 1.71 or less.When the refractive index of organic electroluminescent compound is 1.71 or less, it can reduce the light reflection loss, and allow more light to be extracted from the outside, and this enhanced light extraction can improve the current efficiency of organic electroluminescent device.

[0033] The organic electroluminescent compound represented by Formula 1 according to one embodiment can be represented by any one of the following Formulas 2-1 to 2-11. [ka] [ka]

[0034] In formulas 2-1 to 2-11, R1 to R4 are as defined in Formula 1; R5~R 20 is R in Eq. aas defined for; However, R1~R 20 At least one of the above is expressed by formula 1-1.

[0035] According to one embodiment, the organic electroluminescent compound represented by Formula 1 can be represented by any one of the following Formulas 3-1 to 3-7. [ka]

[0036] In formulas 3-1 to 3-7, R1 to R4 are as defined in Formula 1; R5~R 16 , R 21 ~R 24 and R c ~R f is R in Eq. a as defined for; However, R1~R 16 , R 21 ~R 24 , and R c ~R f At least one of the above is expressed by formula 1-1.

[0037] According to one embodiment, the organic electroluminescent compound represented by Formula 1 can be represented by any one of the following Formulas 4-1 to 4-6. [ka]

[0038] In formulas 4-1 to 4-6, X is NR 29 , O, S, or CR 30 R 31 represents; R1 to R4 are as defined in Formula 1; R5~R 12 and R 25 ~R 31 is R in Eq. aas defined for; However, R1 to R12 and R 25 ~R 31 At least one of the above is expressed by formula 1-1.

[0039] According to one embodiment, the organic electroluminescent compounds represented by Formula 1 can be more specifically exemplified by, but not limited to, the following compounds: [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]

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[0040] In the above compound, D n means that n hydrogen atoms are replaced with deuterium, where n is from 1 to the maximum number of hydrogen atoms in the compound.

[0041] The compound represented by formula 1 according to the present disclosure can be produced by a synthesis method known to those skilled in the art, such as, but not limited to, the synthesis method disclosed in Patent Document 3.

[0042] Hereinafter, an organic electroluminescent device to which the aforementioned organic electroluminescent compound is applied will be described.

[0043] An organic electroluminescent device according to one embodiment includes a first electrode; a second electrode; and at least one organic layer sandwiched between the first and second electrodes. The organic layers include a hole transport layer, an emitting layer, a hole auxiliary layer, an electron blocking layer, and an emitting auxiliary layer. According to one embodiment, at least one of the hole transport layer, the emitting layer, the hole auxiliary layer, the electron blocking layer, and the emitting auxiliary layer may include an organic electroluminescent compound represented by Formula 1. For example, the hole transport layer may include an organic electroluminescent compound of Formula 1. According to one embodiment, the organic electroluminescent material of the present disclosure includes at least one compound selected from the group consisting of C-1 to C-750 and C2-1 to C2-250. The organic electroluminescent material may be included in the same organic layer, such as the hole transport layer.

[0044] An emitting layer according to one embodiment may include a first host compound and a second host compound, wherein the weight ratio of the first host compound to the second host compound in the emitting layer may be in the range of about 1:99 to about 99:1, preferably about 10:90 to about 90:10, more preferably about 30:70 to about 70:30, more preferably about 40:60 to about 60:40, and even more preferably about 50:50.

[0045] In addition to the hole transport layer, light-emitting layer, hole auxiliary layer, electron blocking layer, and light-emitting auxiliary layer, the organic layer may further include at least one layer selected from the group consisting of a hole injection layer, an electron transport layer, an electron injection layer, an intermediate layer, a hole blocking layer, and an electron buffer layer. The organic layer may further include an amine-based compound and / or an azine-based compound other than the light-emitting material according to the present disclosure. Specifically, the hole injection layer, hole transport layer, hole auxiliary layer, light-emitting layer, light-emitting auxiliary layer, or electron blocking layer may contain an amine-based compound, such as an arylamine-based compound or a styrylarylamine-based compound, as the hole injection material, hole transport material, hole auxiliary material, light-emitting material, light-emitting auxiliary material, and electron blocking material. In addition, the electron transport layer, electron injection layer, electron buffer layer, and hole blocking layer may contain an azine-based compound as the electron transport material, electron injection material, electron buffer material, and hole blocking material. The organic layer may also further comprise at least one metal selected from the group consisting of organometallics of Group 1 metals, Group 2 metals, Period 4 transition metals, Period 5 transition metals, lanthanides, and d-transition elements of the periodic table, or at least one complex compound containing such a metal.

[0046] The organic electroluminescent compound according to one embodiment can be used as a light-emitting material for a white organic light-emitting device. The white organic light-emitting device can have various structures, such as a parallel side-by-side arrangement method, a stacked arrangement method, or a CCM (color conversion material) method, depending on the arrangement of R (red), G (green), YG (yellow-green), or B (blue) light-emitting units. In addition, the organic electroluminescent compound according to one embodiment can also be applied to an organic electroluminescent device containing QD (quantum dot).

[0047] One of the first electrode and the second electrode may be an anode, and the other may be a cathode. Herein, the first electrode and the second electrode may be formed as a transparent conductive material, a semi-transparent conductive material, or a reflective conductive material, respectively. The organic electroluminescent device may be a top-emitting, bottom-emitting, or dual-emitting type depending on the type of material forming the first electrode and the second electrode.

[0048] A hole injection layer, a hole transport layer, an electron blocking layer, or a combination thereof may be used between the anode and the light-emitting layer. The hole injection layer may be multi-layered to lower the hole injection barrier (or hole injection voltage) from the anode to the hole transport layer or electron blocking layer, where each of the layers may simultaneously use two compounds. The hole injection layer may also be doped as a p-dopant. The electron blocking layer may also be disposed between the hole transport layer (or hole injection layer) and the light-emitting layer, and may confine excitons within the light-emitting layer by preventing electron overflow from the light-emitting layer, thereby preventing light leakage. The hole transport layer or electron blocking layer may be multi-layered, where each layer may use multiple compounds.

[0049] An electron buffer layer, a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof may be used between the light-emitting layer and the cathode. The electron buffer layer may be multilayered to control electron injection and improve the interfacial properties between the light-emitting layer and the electron injection layer, where each multilayer may simultaneously use two compounds. A hole blocking layer may be disposed between the electron transport layer (or electron injection layer) and the light-emitting layer to block holes from reaching the cathode, thereby improving the probability of recombination of electrons and holes in the light-emitting layer. The hole blocking layer or electron transport layer may also be multilayered, where multiple compounds may be used in each layer. The electron injection layer may also be doped with an n-dopant.

[0050] The light-emitting auxiliary layer can be disposed between the anode and the light-emitting layer or between the cathode and the light-emitting layer. When the light-emitting auxiliary layer is disposed between the anode and the light-emitting layer, it can be used to promote hole injection and / or hole transport or to prevent electron overflow. When the light-emitting auxiliary layer is disposed between the cathode and the light-emitting layer, it can be used to promote electron injection and / or electron transport or to prevent hole overflow. In addition, a hole auxiliary layer can be disposed between the hole transport layer (or hole injection layer) and the light-emitting layer and can be effective in promoting or blocking the hole transport rate (or hole injection rate), thereby allowing the charge balance to be controlled. When an organic electroluminescent device includes two or more hole transport layers, the additional hole transport layer can be used as a hole auxiliary layer or an electron blocking layer. The light-emitting auxiliary layer, hole auxiliary layer, or electron blocking layer can have the effect of improving the efficiency and / or life of the organic electroluminescent device.

[0051] In the organic electroluminescent device of the present disclosure, at least one layer selected from a chalcogenide layer, a metal halide layer, and a metal oxide layer (hereinafter referred to as "surface layer") may be disposed on the inner surface of one or both of the pair of electrodes. Specifically, a chalcogenide (including oxide) layer of silicon and aluminum is preferably disposed on the anode side of the electroluminescent medium layer, and a metal halide layer or a metal oxide layer is preferably disposed on the cathode side of the electroluminescent medium layer. The surface layer can provide operational stability for the organic electroluminescent device. Preferably, the chalcogenide is SiO X (1≦X≦2), AlO X (1≦X≦1.5), SiON, SiAlON, etc.; metal halides include LiF, MgF2, CaF2, rare earth metal fluorides, etc.; metal oxides include Cs2O, Li2O, MgO, SrO, BaO, CaO, etc.

[0052] In addition, in the organic electroluminescent device of the present disclosure, a mixed region of an electron transport compound and a reductive dopant, or a mixed region of a hole transport compound and an oxidative dopant, can be disposed on the surface of at least one of a pair of electrodes. In this case, the electron transport compound is reduced to an anion, thereby making it easier to inject and transport electrons from the mixed region into the electroluminescent medium. Furthermore, the hole transport compound is oxidized to a cation, thereby making it easier to inject and transport holes from the mixed region into the electroluminescent medium. Preferably, the oxidative dopant can include various Lewis acids and acceptor compounds, and the reductive dopant can include alkali metals, alkali metal compounds, alkaline earth metals, rare earth metals, and mixtures thereof. Furthermore, an organic electroluminescent device having two or more light-emitting layers and emitting white light can be prepared using a reductive dopant layer as a charge generation layer.

[0053] An organic electroluminescent device according to an embodiment of the present disclosure may be an organic electroluminescent device having a tandem structure. In the case of a tandem organic electroluminescent device according to an embodiment, a single light-emitting unit (light-emitting unit) may be formed by connecting two or more units via a charge-generating layer. The organic electroluminescent device may include two or more light-emitting units, for example, three or more light-emitting units, each having a first electrode and a second electrode facing each other on a substrate and an emitting layer emitting light in a specific wavelength range stacked between the first and second electrodes. It may include multiple light-emitting units, each of which may include a hole-transporting zone, an emitting layer, and an electron-transporting zone. The hole-transporting zone may include a hole-injection layer and a hole-transporting layer, and the electron-transporting zone may include an electron-transporting layer and an electron-injection layer. According to an embodiment, three or more light-emitting layers may be included in the light-emitting unit. The multiple light-emitting units may emit the same color or different colors. Furthermore, one light-emitting unit can include one or more light-emitting layers, and the multiple light-emitting layers can be light-emitting layers of the same color or different colors. It can also include one or more charge-generating layers disposed between each light-emitting unit. A charge-generating layer refers to a layer that generates holes and electrons when a voltage is applied. When three or more light-emitting units are present, a charge-generating layer can be disposed between each light-emitting unit. In this case, the multiple charge-generating layers can be the same or different from each other. By disposing a charge-generating layer between the light-emitting units, the current efficiency in each light-emitting unit can be increased and charge can be smoothly distributed. Specifically, a charge-generating layer can be provided between two adjacent stacks, which can be useful for driving a tandem organic electroluminescent device using only an anode-cathode pair without a separate internal electrode disposed between the stacks.

[0054] The charge generation layer may be composed of an N-type charge generation layer and a P-type charge generation layer. The N-type charge generation layer may be doped with an alkali metal, an alkaline earth metal, or a compound of an alkali metal and an alkaline earth metal. The alkali metal may include one selected from the group consisting of Li, Na, K, Rb, Cs, Fr, Yb, and combinations thereof. The alkaline earth metal may include one selected from the group consisting of Be, Mg, Ca, Sr, Ba, Ra, and combinations thereof. The P-type charge generation layer may be made of a metal or organic material doped with a P-type dopant. For example, the metal may be made of an alloy of one or more selected from the group consisting of Al, Cu, Fe, Pb, Zn, Au, Pt, W, In, Mo, Ni, and Ti. Additionally, commonly used materials may be used as host materials for the P-type dopants and P-type doped organic materials.

[0055] The organic electroluminescent device according to one embodiment may further comprise at least one dopant in the light-emitting layer.

[0056] The dopant contained in the organic electroluminescent device of the present disclosure can be at least one phosphorescent or fluorescent dopant, preferably phosphorescent dopant.The phosphorescent dopant material applied to the organic electroluminescent device of the present disclosure is not particularly limited, but can be preferably a complex compound of a metal atom selected from iridium (Ir), osmium (Os), copper (Cu) and platinum (Pt), more preferably an ortho-metalated complex compound of a metal atom selected from iridium (Ir), osmium (Os), copper (Cu) and platinum (Pt), and even more preferably an ortho-metalated iridium complex compound.

[0057] The dopant contained in the organic electroluminescent device of the present disclosure may be, but is not limited to, a compound represented by the following formula 101: [ka]

[0058] In Equation 101, L is the following structure 1 to 3: [ka] One of the following is selected from R 100 ~R 103 are each independently hydrogen, deuterium, halogen, unsubstituted or substituted with deuterium and / or halogen (C1-C 30 ) alkyl, substituted or unsubstituted (C3-C 30 ) cycloalkyl, substituted or unsubstituted (C6-C 30 )aryl, cyano, substituted or unsubstituted (3-30 membered) heteroaryl, or substituted or unsubstituted (C1-C 30 ) alkoxy; or may be joined with adjacent substituents to form a ring, for example, with pyridine to form a ring such as substituted or unsubstituted quinoline, substituted or unsubstituted benzofuropyridine, substituted or unsubstituted benzothienopyridine, substituted or unsubstituted indenopyridine, substituted or unsubstituted benzofuroquinoline, substituted or unsubstituted benzothienoquinoline, or substituted or unsubstituted indenoquinoline; R 104 ~R 107 are each independently hydrogen, deuterium, halogen, unsubstituted or substituted with deuterium and / or halogen (C1-C 30 ) alkyl, substituted or unsubstituted (C3-C 30 ) cycloalkyl, substituted or unsubstituted (C6-C 30 )aryl, substituted or unsubstituted (3-30 membered)heteroaryl, cyano, or substituted or unsubstituted (C1-C 30 ) alkoxy; or may be combined with adjacent substituents to form a ring, for example, with benzene to form a ring such as substituted or unsubstituted naphthalene, substituted or unsubstituted fluorene, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzofuran, substituted or unsubstituted indenopyridine, substituted or unsubstituted benzofuropyridine, or substituted or unsubstituted benzothienopyridine; R 201 ~R 220are each independently hydrogen, deuterium, halogen, unsubstituted or substituted with deuterium and / or halogen (C1-C 30 ) alkyl, substituted or unsubstituted (C3-C 30 ) cycloalkyl, or substituted or unsubstituted (C6-C 30 ) aryl; or may be joined with adjacent substituents to form a substituted or unsubstituted ring; s represents an integer of 1 to 3.

[0059] In particular, specific examples of dopant compounds include, but are not limited to, the following: [ka] [ka] [ka] [ka] [ka]

[0060] To form each layer of the organic electroluminescent device of the present disclosure, a dry film-forming method such as vacuum evaporation, sputtering, plasma, ion plating, etc., or a wet film-forming method such as spin coating, dip coating, flow coating, etc., can be used. When using a wet film-forming method, a thin film can be formed by dissolving or diffusing the material forming each layer in any suitable solvent such as ethanol, chloroform, tetrahydrofuran, dioxane, etc. The solvent can be any solvent in which the material forming each layer can be dissolved or diffused and has no problem in film-forming ability.

[0061] When forming a layer by using organic electroluminescent compound according to an embodiment, the layer can be formed by the method listed above, and in many cases can be formed by co-evaporation or mixture evaporation.Co-evaporation is the mixture evaporation method that two or more materials are put into each separate crucible source, and current is passed through both cells at the same time to evaporate the material;Mixture evaporation is the method that two or more materials are mixed in one crucible source before deposition, and then current is passed through one cell to evaporate the material.

[0062] According to one embodiment, the present disclosure can provide a display device comprising the organic electroluminescent compound represented by Formula 1. In addition, the organic electroluminescent device of the present disclosure can be used to prepare display devices such as smartphones, tablets, notebooks, PCs, TVs, or vehicle display devices, or lighting devices such as outdoor or indoor lighting.

[0063] Hereinafter, methods for preparing compounds according to the present disclosure will be described in relation to methods for synthesizing representative compounds or intermediate compounds in order to provide a detailed understanding of the present disclosure. [Example]

[0064] [Example 1] Preparation of Compound C-51 [ka] 1) Synthesis of Compound A 2-(4-Bromophenyl)bicyclo[2.2.1]heptane (18.3 g, 72.9 mmol), 4-(adamantan-1-yl)aniline (21.5 g, 94.7 mmol), Pd(OAc) (0.818 g, 3.64 mmol), S-Phos (2.99 g, 7.29 mmol), NaOt-Bu (10.5 g, 109 mmol), and 300 mL of o-xylene were added to a flask and dissolved. The reaction mixture was then stirred under reflux at 180 °C for 4 hours. Upon completion of the reaction, the mixture was separated by column chromatography to obtain compound A (18.0 g, yield: 62%).

[0065] 2) Synthesis of Compound C-51 2-Iodo-9,9,10,10-tetramethyl-phenanthrene (7.00 g, 19.3 mmol), compound A (8.45 g, 21.3 mmol), Pd(dba) (0.885 g, 0.966 mmol), P(t-Bu) (0.821 g, 1.93 mmol), NaOt-Bu (3.71 g, 38.6 mmol), and 100 mL of toluene were added to a flask and dissolved. The reaction mixture was then stirred under reflux for 1 hour. Upon completion of the reaction, methanol was added to the reaction solution to form a solid, which was filtered under reduced pressure and then separated by column chromatography to obtain compound C-51 (3.7 g, yield: 30%).

[0066] [Table 1]

[0067] [Example 2] Synthesis of Compound C-52 [ka] 3-Bromo-9,9,10,10-tetramethyl-phenanthrene (15.0 g, 47.6 mmol), compound A (19.9 g, 50.0 mmol), Pd(dba) (2.18 g, 2.38 mmol), P(t-Bu) (2.02 g, 4.76 mmol), NaOt-Bu (9.15 g, 95.2 mmol), and 250 mL of toluene were added to a flask and dissolved. The reaction mixture was then stirred under reflux for 1 hour. Upon completion of the reaction, methanol was added to the reaction solution to form a solid, which was filtered under reduced pressure and then separated by column chromatography to obtain compound C-52 (8.5 g, yield: 28.3%).

[0068] [Table 2]

[0069] In the following description, the method and results of measuring the refractive index of the organic electroluminescent compound according to the present disclosure will be described in order to understand the present disclosure in detail.

[0070] [Examples 3-6] Measurement of refractive index of organic electroluminescent compounds according to the present disclosure To obtain the refractive index of the organic electroluminescent compound according to the present disclosure, the material to be measured for refractive index is placed in a cell in a vacuum deposition apparatus, and the vacuum in the chamber is adjusted to 10 -6 Evacuation continued until a pressure of 1000 kJ / cm2 was reached. A current was then applied to the cell to evaporate the material, thereby preparing a 30 nm thick sample on a silicon wafer substrate.

[0071] The refractive index was measured using an ellipsometer, specifically, a JA Woollam M-2000 manufactured by Wizoptics, at an incident angle of 60° in the wavelength range of 350 nm to 800 nm, and the refractive index at 620 nm was used as the reference.

[0072] The refractive index measurements of representative compounds of the present disclosure using the above measurement method are shown in Table 1 below.

[0073] [Table 3]

[0074] From Table 1 above, it can be seen that the refractive index of the organic electroluminescent compound according to the present disclosure is 1.71 or less.Therefore, it can be expected that when the organic electroluminescent compound of Formula 1 according to the present disclosure is used in organic electroluminescent device, the light reflection loss will be reduced, thereby improving the current efficiency of the device.

[0075] In order to provide a detailed understanding of the present disclosure, the preparation method of an organic electroluminescent device comprising the organic electroluminescent compound according to the present disclosure and the device characteristics thereof will be described below.

[0076] [Device Examples 1-3] Preparation of OLEDs containing organic electroluminescent compounds according to the present disclosure An OLED according to the present disclosure was prepared. First, a transparent indium tin oxide (ITO) thin film (10 Ω / sq) (Geomatec Co., Ltd.) on a glass substrate for an OLED was ultrasonically cleaned in acetone and isopropyl alcohol, then stored in isopropyl alcohol, and then used. The ITO substrate was then mounted on a substrate holder in a vacuum evaporation system. Compound HI-1 was then introduced into one cell of the vacuum evaporation system, and compound HT-1 was introduced into the other cell. The two materials were evaporated at different rates, and compound HI-1 was deposited with a doping amount of 5 wt. % based on the total amount of compound HI-1 and compound HT-1 to form a hole injection layer with a thickness of 10 nm. Compound HT-1 was then deposited on the hole injection layer as a first hole transport layer with a thickness of 90 nm. Next, the compound listed in Table 2 below was introduced into another cell of the vacuum evaporation apparatus as a second hole transport layer compound and evaporated by passing a current through the cell, thereby forming a second hole transport layer having a thickness of 60 nm on the first hole transport layer. Next, compound HT-2 was introduced into another cell of the vacuum evaporation apparatus as a third hole transport layer compound and evaporated by passing a current through the cell, thereby forming a third hole transport layer having a thickness of 7.5 nm on the second hole transport layer. After forming the hole injection layer and the hole transport layer, an emitting layer was formed thereon as follows: compound H-1 and compound H-2 were introduced into two cells of the vacuum evaporation apparatus as hosts, and compound D-39 was introduced into another cell as a dopant. Two host materials were evaporated in a 1:1 ratio, and dopant materials were simultaneously evaporated in different ratios, with a doping amount of 2 wt % based on the total amount of host and dopant, to form an emitting layer with a thickness of 36 nm on the third hole transport layer. Compound B-2 was then evaporated on the emitting layer as an electron buffer material with a thickness of 5 nm. Compounds ET-2 and EI-1 were then evaporated in a 2:1 weight ratio as electron transport materials to form an electron transport layer with a thickness of 25 nm. Compound EI-1 was then evaporated on the electron transport layer as an electron injection layer with a thickness of 2 nm, and then an 80 nm thick Al cathode was evaporated on the electron injection layer using a separate vacuum evaporation system. In this way, an OLED was fabricated.Ten of each of the compounds used for all of the materials. -6 It was purified by vacuum sublimation at torr.

[0077] Comparative Examples 1 and 2: Preparation of OLEDs containing conventional compounds as second hole transport layer materials An OLED was fabricated in the same manner as Device Example 1, except that the compound shown in Table 2 below was used as the second hole transport layer material.

[0078] The driving voltage, current efficiency and CIE color coordinates at a luminance of 1,000 nits of the organic electroluminescent devices of Examples 1 to 3 and Comparative Examples 1 and 2 prepared as above were measured, and the results are shown in Table 2 below.

[0079] [Table 4]

[0080] From Table 2 above, it can be seen that the organic electroluminescent device that comprises the organic electroluminescent compound according to the present disclosure as hole transport material exhibits lower driving voltage and / or higher efficiency characteristics compared with the organic electroluminescent device that comprises conventional compound as hole transport material.

[0081] The compounds used in the above device examples and comparative examples are specifically shown in Table 3 below.

[0082] [Table 5]

[0083] [Table 6]

Claims

1. Formula 1 below: 【Chemistry 1】 [In the formula, Ring A and ring B are each independently substituted or unsubstituted (C ６ ~C ３０ ) arene, or substituted or unsubstituted (3- to 30-membered) heteroarene; R １ ~R ４ , R ａ , and R ｂ are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C １ ~C ３０ ) alkyl, substituted or unsubstituted (C ６ ~C ３０ ) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, substituted or unsubstituted (C ３ ~C ３０ ) cycloalkyl, substituted or unsubstituted (C １ ~C ３０ ) alkoxy, substituted or unsubstituted tri(C １ ~C ３０ ) alkylsilyl, substituted or unsubstituted di(C １ ~C ３０ ) alkyl(C ６ ~C ３０ ) arylsilyl, substituted or unsubstituted (C １ ~C ３０ ) alkyldi(C ６ ~C ３０ ) arylsilyl, substituted or unsubstituted tri(C ６ ~C ３０ ) arylsilyl, (C ３ ~C ３０ ) an aliphatic ring and (C ６ ~C ３０ ) substituted or unsubstituted fused rings with aromatic rings, substituted or unsubstituted mono- or di-(C １ ~C ３０ ) alkylamino, substituted or unsubstituted mono- or di(C ６ ~C ３０ ) arylamino, substituted or unsubstituted (C １ ~C ３０ ) alkyl(C ６ ~C ３０ )arylamino, substituted or unsubstituted mono- or di(3- to 30-membered)heteroarylamino, or substituted or unsubstituted (C ６ ~C ３０ ) aryl(3-30 membered)heteroarylamino; or may be combined with adjacent substituents to form a ring; However, R １ ~R ４ , R ａ , and R ｂ At least one of the following formula 1-1: 【Chemistry 2】 (In the formula, L １ ~L ３ are each independently a single bond, a substituted or unsubstituted (C ６ ~C ３０ ) arylene, or substituted or unsubstituted (3- to 30-membered) heteroarylene; Ar １ and Ar ２ are each independently substituted or unsubstituted (C ６ ~C ３０ )aryl, substituted or unsubstituted (3-30 membered)heteroaryl, or substituted or unsubstituted (C ３ ~C ３０ ) represents cycloalkyl; However, Ar １ and Ar ２ At least one of is substituted or unsubstituted (C ３ ~C ３０ ) provided that it is cycloalkyl) provided that: n and m are integers of 1 to 8, and when n and m are integers of 2 or more, R ａ and R ｂ may be the same or different. An organic electroluminescent compound represented by the formula:

2. The substituted arene, the substituted heteroarene, the substituted alkyl, the substituted aryl(ene), the substituted heteroaryl(ene), the substituted cycloalkyl, the substituted alkoxy, the substituted trialkylsilyl, the substituted dialkylarylsilyl, the substituted alkyldiarylsilyl, the substituted triarylsilyl, the substituted fused ring of an aliphatic ring and an aromatic ring, the substituted mono- or dialkylamino, the substituted mono- or diarylamino, the substituted alkylarylamino, the substituted mono- or diheteroarylamino, and the substituted arylheteroarylamino each independently represent deuterium; halogen; cyano; carboxyl; nitro; hydroxy; (C １ ~C ３０ ) alkyl; halo(C １ ~C ３０ ) alkyl; (C ２ ~C ３０ ) alkenyl; (C ２ ~C ３０ ) alkynyl; (C １ ~C ３０ ) alkoxy; (C １ ~C ３０ ) alkylthio; (C ３ ~C ３０ ) cycloalkyl; (C ３ ~C ３０ ) cycloalkenyl; (3- to 7-membered) heterocycloalkyl; (C ６ ~C ３０ ) aryloxy; (C ６ ~C ３０ ) arylthio; unsubstituted or (C ６ ~C ３０ ) aryl-substituted (5- to 30-membered) heteroaryl; unsubstituted or (5- to 30-membered) heteroaryl-substituted (C ６ ~C ３０ ) aryl; tri(C １ ~C ３０ ) alkylsilyl; tri(C ６ ~C ３０ ) arylsilyl; di(C １ ~C ３０ ) alkyl(C ６ ~C ３０ ) arylsilyl; (C １ ~C ３０ ) alkyldi(C ６ ~C ３０ ) arylsilyl; (C ３ ~C ３０ ) an aliphatic ring and (C ６ ~C ３０ ) condensed ring with an aromatic ring; amino; mono- or di(C １ ~C ３０ ) alkylamino; substituted or unsubstituted mono- or di(C ６ ~C ３０ ) arylamino; (C １ ~C ３０ ) alkyl(C ６ ~C ３０ ) arylamino; mono- or di(3- to 30-membered) heteroarylamino; (C １ ~C ３０ ) alkyl(3-30 membered)heteroarylamino; (C ６ ~C ３０ ) aryl(3-30 membered)heteroarylamino; (C １ ~C ３０ ) alkylcarbonyl; (C １ ~C ３０ ) alkoxycarbonyl; (C ６ ~C ３０ ) arylcarbonyl; (C ６ ~C ３０ ) arylphosphinyl, di(C ６ ~C ３０ ) arylboronyl; di(C １ ~C ３０ ) alkylboronyl; (C １ ~C ３０ ) alkyl(C ６ ~C ３０ ) arylboronyl; (C ６ ~C ３０ ) Al (C １ ~C ３０ ) alkyl; (C １ ~C ３０ ) alkyl(C ６ ~C ３０ 2. The organic electroluminescent compound of claim 1, wherein the organic electroluminescent compound is substituted with at least one selected from the group consisting of aryl, ...

3. Formula 1 is the following formulas 2-1 to 2-11: 【Transformation 3】 【Chemistry 4】 (In the formula, R １ ~R ４ is as defined in claim 1; R ５ ~R ２０ is R in claim 1 ａ as defined for However, R １～ R ２０ provided that at least one of is represented by formula 1-1 in claim 1) 2. The organic electroluminescent compound according to claim 1, wherein the compound is represented by any one of the following formulas:

4. Formula 1 is the following formulas 3-1 to 3-7: 【Transformation 5】 (In the formula, R １ ~R ４ is as defined in claim 1; R ５ ~R １６ , R ２１ ~R ２４ , and R ｃ ~R ｆ is as defined in claim 1; However, R １ ~R １６ , R ２１ ~R ２４ and R ｃ ~R ｆ provided that at least one of is represented by formula 1-1 in claim 1) 2. The organic electroluminescent compound according to claim 1, wherein the compound is represented by any one of the following formulas:

5. Formula 1 is the following formulas 4-1 to 4-6: 【Transformation 6】 (In the formula, X is NR ２９ , O, S, or CR ３０ R ３１ represents; R １ ~R ４ is as defined in claim 1; R ５ ~R １２ and R ２５ ~R ３１ is R in claim 1 ａ as defined for However, R １ ~R １２ and R ２５ ~R ３１ provided that at least one of is represented by formula 1-1 in claim 1) 2. The organic electroluminescent compound according to claim 1, wherein the compound is represented by any one of the following formulas:

6. R １ ~R ４ are each independently hydrogen, deuterium, substituted or unsubstituted (C １ ~C ３０ ) alkyl, substituted or unsubstituted (C ６ ~C ３０ )aryl, substituted or unsubstituted (3-30 membered)heteroaryl, or substituted or unsubstituted (C ３ ~C ３０ 2. The organic electroluminescent compound according to claim 1, wherein R represents cycloalkyl.

7. Ar １ and Ar ２ 2. The organic electroluminescent compound according to claim 1, wherein at least one of represents cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, bicyclo[2.1.1]hexyl, bicyclo[2.2.1]heptyl, bicyclo[3.1.1]heptyl, bicyclo[2.2.2]octyl, bicyclo[3.2.1]octyl, adamantanyl, 2,3-dihydro-1H-indenyl, 1,2,3,4-tetrahydronaphthalenyl, or 6,7,8,9-tetrahydro-5H-benzo[7]annulenyl.

8. 2. The organic electroluminescent compound according to claim 1, wherein the organic electroluminescent compound represented by Formula 1 has a refractive index of 1.71 or less.

9. The organic luminescent compound represented by formula 1 is the following compound: 【Transformation 7】 【Transformation 8】 【Chemistry 9】 【Chemistry 10】 【Chemistry 11】 【Chemistry 12】 【Chemistry 13】 【Chemistry 14】 【Chemistry 15】 【Chemistry 16】 【Chemistry 17】 [Chemistry 18] 【Chemistry 19】 【Chemistry 20】 【Chemistry 21】 【Chemistry 22】 【Chemistry 23】 【Chemistry 24】 【Chemistry 25】 【Chemistry 26】 【Chemistry 27】 【Chemistry 28】 【Chemistry 29】 【Transformation 30】 【Chemistry 31】 【Chemistry 32】 【Transformation 33】 【Transformation 34】 【Chemistry 35】 【Transformation 36】 【Chemistry 37】 【Transformation 38】 【Chemistry 39】 【Chemistry 40】 【Chemistry 41】 【Chemistry 42】 【Chemistry 43】 【Chemistry 44】 【Chemistry 45】 【Chemistry 46】 【Chemistry 47】 【Chemistry 48】 【Chemistry 49】 [Transformation 50] (In the formula, D ｎ means that n hydrogen atoms are replaced with deuterium, where n is from 1 to the maximum number of hydrogen atoms in the compound.

2. The organic electroluminescent compound according to claim 1, selected from:

10. An organic electroluminescent material comprising the organic electroluminescent compound of claim 1.

11. An organic electroluminescent device comprising the organic electroluminescent compound of claim 1.

12. 12. The organic electroluminescent device according to claim 11, wherein the organic electroluminescent compound is contained in at least one layer of a hole transport layer, a light-emitting layer, a hole auxiliary layer, an electron blocking layer, and a light-emitting auxiliary layer.

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