Polycyclic aromatic derivative compounds and organic electroluminescent devices using the same

Abstract

The present application relates to polycyclic aromatic derivative compounds and high-efficiency and long-life organic electroluminescent devices having significantly improved luminous efficiency by using the same. The present application can realize an organic electroluminescent device having high efficiency and long life, and thus can be effectively used for industrial applications including flat panel display devices, flexible display devices, monochrome or white flat lighting devices, and monochrome or white flexible lighting devices.

Description

Technical Field

[0001] This invention relates to polycyclic aromatic derivatives and efficient and durable organic electroluminescent devices using said polycyclic aromatic derivatives with significantly improved luminescence efficiency. Background Technology

[0002] Organic electroluminescent devices are self-emissive devices in which electrons injected from the electron injection electrode (cathode) recombine with holes injected from the hole injection electrode (anode) in the emissive layer to form excitons, which emit light while releasing energy. Such organic electroluminescent devices offer advantages such as low driving voltage, high brightness, wide viewing angle, and short response time, and can be applied to full-color light-emitting flat panel displays. Due to these advantages, organic electroluminescent devices have attracted attention as a next-generation light source.

[0003] The above-mentioned characteristics of organic electroluminescent devices are achieved through structural optimization of the organic layer of the device, and are supported by stable and effective materials used for the organic layer (e.g., hole injection materials, hole transport materials, luminescent materials, electron transport materials, electron injection materials, and electron blocking materials). However, further research is still needed to develop structurally optimized organic layers for organic electroluminescent devices and stable and effective materials for the organic layers of organic electroluminescent devices.

[0004] Therefore, there is a continuous need to develop structures for organic electroluminescent devices that are optimized to improve their luminescence properties, as well as new materials that can support the optimized structures of organic electroluminescent devices. Summary of the Invention

[0005] Technical issues

[0006] Therefore, the present invention aims to provide an organic compound for use in the organic layer of an organic electroluminescent device to achieve high efficiency and long lifespan of the device. The present invention also aims to provide an organic electroluminescent device comprising said organic compound.

[0007] Technical solution

[0008] One aspect of the present invention provides organic compounds represented by formula I or formula II:

[0009] [Formula I]

[0010]

[0011] [Formula II]

[0012]

[0013] The structures of Formulas I and II, the specific compounds that can be represented by Formulas I and II, and the limitations of rings A to F, X, Y, L1 to L4 and Z are as follows.

[0014] The present invention also provides an organic electroluminescent device comprising a first electrode, a second electrode opposite to the first electrode, and one or more organic layers between the first electrode and the second electrode, wherein one of the organic layers comprises at least one of a specific polycyclic aromatic compound that can be represented by Formula I or Formula II.

[0015] Beneficial effects

[0016] The polycyclic aromatic derivatives of the present invention can be used in the organic layer of organic electroluminescent devices to achieve high efficiency and long lifespan of the devices. Detailed Implementation

[0017] The invention will now be described in more detail.

[0018] This invention relates to polycyclic aromatic derivatives for organic electroluminescent devices represented by formula I or formula II:

[0019] [Formula I]

[0020]

[0021] Rings A through D may be identical or different from each other, and each is independently a substituted or unsubstituted C6-C ring. 50 Monocyclic or polycyclic aromatic hydrocarbon rings, or substituted or unsubstituted C2-C... 50 Monocyclic or polycyclic aromatic heterocycles, where X is selected from B, P, P=O, P=S, and Al, and L1 and L2 are either the same or different from each other, and each is an independent single bond or selected from: -O-, -S-, and -Se-, where Y is a single bond or selected from... -O-, -S-, and -Se-, each Z independently is CR or N, R and R1 to R 10 They may be the same as or different from each other, and each is independently selected from hydrogen, deuterium, substituted or unsubstituted C1-C. 30 Alkyl, substituted or unsubstituted C1-C 30 Alkenyl, substituted or unsubstituted C6-C 50 Aryl, substituted or unsubstituted C3-C 30 cycloalkyl, substituted or unsubstituted C2-C 30 Heterocyclic alkyl, substituted or unsubstituted C2-C 50 heteroaryl, substituted or unsubstituted C1-C 30 Alkoxy, substituted or unsubstituted C6-C 30 aryloxy groups, substituted or unsubstituted C1-C 30 Alkyl thio, substituted or unsubstituted C5-C 30Arylthio, substituted or unsubstituted amino, substituted or unsubstituted silyl, nitro, cyano, and halogen, provided that each of L1 and L2 is At this time, R1 may optionally bond with adjacent ring C or ring D to form alicyclic or aromatic monocyclic or polycyclic rings, provided that R6 to R 10 Each of the following is optionally bonded to ring A or R to form an alicyclic or aromatic monocyclic or polycyclic ring; R is optionally bonded to ring D to form an alicyclic or aromatic monocyclic or polycyclic ring; R2 and R3 are optionally linked to each other to form an alicyclic or aromatic monocyclic or polycyclic ring; R4 and R5 are optionally linked to each other to form an alicyclic or aromatic monocyclic or polycyclic ring; R7 and R8 are optionally linked to each other to form an alicyclic or aromatic monocyclic or polycyclic ring; R9 and R... 10 Optionally linked to each other to form alicyclic or aromatic monocyclic or polycyclic rings, a substituted or unsubstituted monocyclic or polycyclic non-aromatic ring optionally fused with ring A to form a fused ring, a substituted or unsubstituted monocyclic or polycyclic non-aromatic ring optionally fused with ring B to form a fused ring, a substituted or unsubstituted monocyclic or polycyclic non-aromatic ring optionally fused with ring C to form a fused ring, a substituted or unsubstituted monocyclic or polycyclic non-aromatic ring optionally fused with ring D to form a fused ring, and rings A and B optionally linked to each other.

[0022] [Formula II]

[0023]

[0024] Rings A through F may be identical or different from each other, and each is independently a substituted or unsubstituted C6-C ring. 50 Monocyclic or polycyclic aromatic hydrocarbon rings, or substituted or unsubstituted C2-C... 50 Monocyclic or polycyclic aromatic heterocycles, where X is selected from B, P, P=O, P=S, and Al, and L1 to L4 are identical or different from each other, and each is an independent single bond or selected from: -O-, -S-, and -Se-, each Z is independently CR or N, R and R1 to R5 are the same or different from each other, and each is independently selected from hydrogen, deuterium, substituted or unsubstituted C1-C. 30 Alkyl, substituted or unsubstituted C1-C 30 Alkenyl, substituted or unsubstituted C6-C 50 Aryl, substituted or unsubstituted C3-C 30 cycloalkyl, substituted or unsubstituted C2-C 30 Heterocyclic alkyl, substituted or unsubstituted C2-C 50 heteroaryl, substituted or unsubstituted C1-C 30 Alkoxy, substituted or unsubstituted C6-C 30 aryloxy groups, substituted or unsubstituted C1-C 30Alkyl thio, substituted or unsubstituted C5-C 30 Arylthio, substituted or unsubstituted amino, substituted or unsubstituted silyl, nitro, cyano, and halogen, provided that each of L1 to L4 is In this configuration, R1 is optionally bonded to adjacent rings C, D, E, or F to form alicyclic or aromatic monocyclic or polycyclic rings, provided that R is optionally bonded to ring D or E to form alicyclic or aromatic monocyclic or polycyclic rings; R2 and R3 are optionally linked to each other to form alicyclic or aromatic monocyclic or polycyclic rings; R4 and R5 are optionally linked to each other to form alicyclic or aromatic monocyclic or polycyclic rings; substituted or unsubstituted monocyclic or polycyclic non-aromatic rings are optionally fused to ring A to form fused rings; substituted or unsubstituted... A monocyclic or polycyclic nonaromatic ring may optionally fuse with ring B to form a fused ring; a substituted or unsubstituted monocyclic or polycyclic nonaromatic ring may optionally fuse with ring C to form a fused ring; a substituted or unsubstituted monocyclic or polycyclic nonaromatic ring may optionally fuse with ring D to form a fused ring; a substituted or unsubstituted monocyclic or polycyclic nonaromatic ring may optionally fuse with ring E to form a fused ring; a substituted or unsubstituted monocyclic or polycyclic nonaromatic ring may optionally fuse with ring F to form a fused ring; and rings A and B may optionally be connected to each other.

[0025] The use of the aforementioned polycyclic aromatic derivatives makes the organic electroluminescent device efficient and durable.

[0026] According to one embodiment of the present invention, the L2 connecting ring C and ring D in Formula I can be provided in two forms, and the two connecting groups L2 can be the same or different from each other, and can form a ring with ring C and ring D, as shown in Formula I-1:

[0027] [Formula I-1]

[0028]

[0029] According to one embodiment of the invention, the linking group L2 in Formula II can be provided in two forms, and the two linking groups L2 can be the same or different from each other, and can form a ring with ring C and ring D, as shown in Formula II-1:

[0030] [Formula II-1]

[0031]

[0032] According to one embodiment of the invention, the linking group L3 in Formula II can be provided in two forms, and the two linking groups L3 can be the same or different from each other, and can form a ring with ring E and ring F, as shown in Formula II-2:

[0033] [Formula II-2]

[0034]

[0035] According to one embodiment of the present invention, in Formula II, the linking group L2 connecting ring C and ring D can be provided in two forms, and the two linking groups L2 can form a ring with ring C and ring D; and in Formula II, the linking group L3 connecting ring E and ring F can be provided in two forms, and the two linking groups L3 can form a ring with ring E and ring F, as shown in Formula II-3:

[0036] [Formula II-3]

[0037]

[0038] The specific structures of Formulas I and II, as well as modified structures of Formulas I and II containing additional rings, can be found in the specific compounds illustrated below.

[0039] As used in this article, in rings A to F, R and R1 to R 10 The term "substituted" in the definition means substituted with one or more substituents selected from: deuterium, cyano, halogen, hydroxyl, nitro, alkyl, haloalkyl, cycloalkyl, alkenyl, ynyl, heteroalkyl, aryl, arylalkyl, alkylaryl, heteroaryl, heteroarylalkyl, alkoxy, amino, silyl, aryloxy, and a mixture of aliphatic-aromatic cyclic groups, or combinations thereof. The term "unsubstituted" in the same definition, as used herein, means without substituents.

[0040] In "substituted or unsubstituted C1-C" 10 Alkyl group, substituted or unsubstituted C6-C 50 In the aryl group, the number of carbon atoms in the alkyl or aryl group indicates the number of carbon atoms constituting the unsubstituted alkyl or aryl moiety, regardless of the number of carbon atoms in the substituents. For example, a phenyl group substituted with butyl at the para position corresponds to a C6 aryl group substituted with C4 butyl.

[0041] As used herein, the expression "forming a ring with an adjacent substituent" means that the corresponding substituent combines with an adjacent substituent to form a substituted or unsubstituted alicyclic or aromatic ring, and the term "adjacent substituent" can mean a substituent on an atom directly bonded to the atom substituted with the corresponding substituent, a substituent located spatially closest to the corresponding substituent, or another substituent on the atom substituted with the corresponding substituent. For example, two substituents substituted at the ortho position on a benzene ring or two substituents on the same carbon atom in an alicyclic ring can be considered "adjacent" to each other.

[0042] The alkyl group can be straight-chain or branched, and specific examples include, but are not limited to, methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methylbutyl, 1-ethylbutyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethylpropyl, 1,1-dimethylpropyl, isohexyl, 2-methylpentyl, 4-methylhexyl, and 5-methylhexyl.

[0043] The alkenyl group is intended to include straight-chain alkenyl and branched alkenyl groups, and may optionally be substituted with one or more additional substituents. The alkenyl group may specifically be vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1-butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, styryl, or styryl, but is not limited thereto.

[0044] The alkynyl group is intended to include both straight-chain and branched alkynyl groups, and may optionally be substituted with one or more additional substituents. The alkynyl group may be, for example, ethynyl or 2-propynyl, but is not limited thereto.

[0045] Cycloalkyl is intended to include both monocyclic and polycyclic cycloalkyl groups, and may optionally be substituted with one or more additional substituents. As used herein, the term "polycyclic" means that the cycloalkyl group may be directly attached to or fused with one or more additional cyclic groups. The additional cyclic groups may be cycloalkyl, and other examples include heterocyclic, aryl, and heteroaryl groups. Cycloalkyl groups may specifically be, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, adamantyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, or cyclooctyl.

[0046] Heterocyclic alkyl groups are intended to include monocyclic and polycyclic heterocyclic alkyl groups interrupted by heteroatoms such as O, S, Se, N, or Si, and may optionally be substituted with one or more additional substituents. As used herein, the term "polycyclic" means that a heterocyclic alkyl group may be directly attached to or fused with one or more additional cyclic groups. The additional cyclic groups may be heterocyclic alkyl groups, and other examples include cycloalkyl, aryl, and heteroaryl groups.

[0047] Aromatic hydrocarbon rings or aryl groups can be monocyclic or polycyclic. Examples of monocyclic aryl groups include, but are not limited to, phenyl, biphenyl, terphenyl, and styrene. Examples of polycyclic aryl groups include naphthyl, anthraceneyl, phenanthryl, pyrene, perylene, and tetraphenyl. The compounds used include methyl, fluorenyl, acenaphathcenyl, triphenylene, and fluoranyl, but the scope of the invention is not limited thereto.

[0048] Aromatic heterocycles or heteroaryl groups are aromatic groups interrupted by one or more heteroatoms. Examples of aromatic heterocycles or heteroaryl groups include, but are not limited to, thiophene, furanyl, pyrrole, imidazolyl, and thiazolyl. azole group, Diazolyl, Triazolyl, Pyridyl, Bipyridyl, Pyrimidinyl, Triazinyl, Triazolyl, Acridineyl, Pyridazinyl, Quinolinyl, Quinazolinyl, Quinoxalinyl, Phtharazineyl, Pyridopyrimidinyl, Pyridopyrazinyl, Pyrazenopyrazinyl, Isoquinolinyl, Indoleyl, Carbazoleyl, Benzo[] Azolyl, benzimidazolyl, benzothiazolyl, benzocarbazole, benzothiophene, dibenzothiophene, benzofuranyl, dibenzofuranyl, phenanthrolinel, thiazolyl, iso azole group, Diazolyl, thiadiazolyl, benzothiazolyl, and phenthiazinyl.

[0049] Aliphatic hydrocarbon rings are non-aromatic rings consisting only of carbon and hydrogen atoms. Aliphatic hydrocarbon rings are intended to include monocyclic or polycyclic aliphatic hydrocarbon rings and may optionally be substituted with one or more additional substituents. As used herein, the term "polycyclic" means that the aliphatic hydrocarbon ring can be directly attached to or fused with one or more additional cyclic groups. These additional cyclic groups can be aliphatic hydrocarbon rings, and other examples include aliphatic heterocyclic groups, aryl groups, and heteroaryl groups. Specific examples of aliphatic hydrocarbon rings include, but are not limited to, cycloalkyl groups such as cyclopropyl, cyclobutyl, cyclopentyl, adamantyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, and cyclooctyl; cycloalkanes such as cyclohexane and cyclopentane; and cycloalkenes such as cyclohexene and cyclopentene.

[0050] Aliphatic heterocycles are aliphatic rings interrupted by one or more heteroatoms such as O, S, Se, N, and Si. Aliphatic heterocycles are intended to include monocyclic or polycyclic aliphatic heterocycles and may optionally be substituted with one or more additional substituents. As used herein, the term "polycyclic" means that an aliphatic heterocycle, such as a heterocyclic alkyl, heterocyclic alkane, or heterocyclic alkene, can be directly attached to or fused with one or more additional cyclic groups. These additional cyclic groups can be aliphatic heterocycles, and other examples include aliphatic hydrocarbon rings, aryl groups, and heteroaryl groups.

[0051] A mixed aliphatic-aromatic ring is a ring in which at least one aliphatic ring and at least one aromatic ring are connected or fused together and the ring as a whole is non-aromatic. A mixed aliphatic-aromatic polycyclic ring may contain one or more heteroatoms selected from N, O, P and S other than carbon (C).

[0052] Alkoxy groups can specifically be methoxy, ethoxy, propoxy, isobutoxy, sec-butoxy, pentoxy, isopentoxy, or hexoxy, but are not limited thereto.

[0053] The silyl group can be, for example, -SiH3, alkylsilyl, arylsilyl, alkylarylsilyl, and arylheteroarylsilyl. Specific examples of silyl groups include trimethylsilyl, triethylsilyl, triphenylsilyl, trimethoxysilyl, dimethoxyphenylsilyl, diphenylmethylsilyl, diphenylvinylsilyl, methylcyclobutylsilyl, and dimethylfuranylsilyl.

[0054] The amino group can be, for example, -NH2, alkylamino, arylamino, and arylheteroarylamino. Arylamino refers to an aryl-substituted amino group, alkylamino refers to an alkyl-substituted amino group, and arylheteroarylamino refers to an amino group substituted with both aryl and heteroaryl groups. Examples of arylamino groups include substituted or unsubstituted monoarylamino groups, substituted or unsubstituted diarylamino groups, and substituted or unsubstituted triarylamino groups. The aryl and heteroaryl moieties in arylamino and arylheteroarylamino groups can be monocyclic or polycyclic aryl and heteroaryl. Arylamino groups can contain two or more aryl moieties, and arylheteroarylamino groups can contain two or more heteroaryl moieties. In this case, the aryl moieties can be monocyclic or polycyclic aryl moieties, or can be composed of both monocyclic and polycyclic aryl moieties. The heteroaryl moieties can be monocyclic or polycyclic heteroaryl moieties, or can be composed of both monocyclic and polycyclic heteroaryl moieties. The aryl and heteroaryl moieties in arylamine and arylheteroarylamine groups can be selected from those exemplified above.

[0055] The aryl groups in aryloxy and arylthio groups are the same as those described above regarding aryl groups. Specific examples of aryloxy groups include, but are not limited to, phenoxy, p-tolyloxy, m-tolyloxy, 3,5-dimethylphenoxy, 2,4,6-trimethylphenoxy, p-tert-butylphenoxy, 3-biphenoxy, 4-biphenoxy, 1-naphthoxy, 2-naphthoxy, 4-methyl-1-naphthoxy, 5-methyl-2-naphthoxy, 1-anthraoxy, 2-anthraoxy, 9-anthraoxy, 1-phenanthoxy, 3-phenanthoxy, and 9-phenanthoxy. The arylthio group can be, for example, phenylthio, 2-methylphenylthio, or 4-tert-butylphenylthio, but is not limited to these.

[0056] The halogen group can be, for example, fluorine, chlorine, bromine or iodine.

[0057] More specifically, the polycyclic aromatic derivatives according to the present invention represented by Formula I or Formula II may be selected from, but are not limited to, the following compounds 1 to 210:

[0058]

[0059]

[0060]

[0061]

[0062]

[0063]

[0064]

[0065]

[0066]

[0067]

[0068]

[0069]

[0070]

[0071]

[0072]

[0073]

[0074]

[0075] The specific substituents in Formula I or Formula II can be clearly seen from the structures of compounds 1 to 210, but are not intended to limit the range of compounds represented by Formula I or Formula II.

[0076] As can be seen from the specific compounds above, the polycyclic aromatic derivatives of the present invention contain B, P, P=O, P=S, or Al, and have a polycyclic aromatic structure. Introducing substituents into the polycyclic aromatic structure enables the synthesis of organic materials possessing the inherent properties of the substituents. For example, the substituents are designed for use in materials for hole injection layers, hole transport layers, light-emitting layers, electron transport layers, electron injection layers, electron blocking layers, and hole blocking layers in organic electroluminescent devices. This introduction satisfies the requirements for materials used in organic layers, resulting in highly efficient organic electroluminescent devices.

[0077] Another aspect of the present invention relates to an organic electroluminescent device comprising a first electrode, a second electrode, and one or more organic layers between the first electrode and the second electrode, wherein one of the organic layers comprises at least one of an organic compound that can be represented by formula I or formula II.

[0078] That is, according to one embodiment of the present invention, the organic electroluminescent device has a structure in which one or more organic layers are disposed between a first electrode and a second electrode. The organic electroluminescent device of the present invention can be manufactured by suitable methods known in the art using suitable materials known in the art, except that an organic compound of formula I or formula II is used to form the corresponding organic layers.

[0079] The organic layer of the organic electroluminescent device according to the present invention can be formed into a single-layer structure. Alternatively, the organic layer can have a multi-layer stacked structure. For example, the organic layer can have a structure including a hole injection layer, a hole transport layer, a hole blocking layer, a light-emitting layer, an electron blocking layer, an electron transport layer, and an electron injection layer, but is not limited to this structure. The number of organic layers is not limited and can be increased or decreased. The preferred structure of the organic layer of the organic electroluminescent device according to the present invention will be described in more detail in the following embodiment section.

[0080] The organic electroluminescent device of the present invention includes an anode, a hole transport layer, a light-emitting layer, an electron transport layer, and a cathode. The organic electroluminescent device of the present invention may optionally include a hole injection layer between the anode and the hole transport layer, and an electron injection layer between the electron transport layer and the cathode. If necessary, the organic electroluminescent device of the present invention may also include one or two intermediate layers, such as a hole blocking layer or an electron blocking layer.

[0081] According to one embodiment of the invention, one of the organic layers between the first electrode and the second electrode may be a light-emitting layer composed of a host and a compound represented by Formula I or Formula II as a dopant. Based on about 100 parts by weight of the host, the content of the dopant in the light-emitting layer is typically in the range of about 0.01 parts by weight to about 20 parts by weight, but is not limited to this range.

[0082] According to one embodiment of the present invention, the main component may be an anthracene derivative represented by formula C:

[0083] [Formula C]

[0084]

[0085] Where R 21 To R 28 Whether they are the same or different from each other, and as defined by R in Equation I or II, Ar9 and Ar 10 They may be the same as or different from each other, and each is independently selected from hydrogen, deuterium, substituted or unsubstituted C1-C. 30 Alkyl, substituted or unsubstituted C6-C 50 Aryl, substituted or unsubstituted C2-C 30 Alkenyl, substituted or unsubstituted C2-C 20 Alkyne group, substituted or unsubstituted C3-C 30 cycloalkyl, substituted or unsubstituted C5-C 30 Cycloalkenyl, substituted or unsubstituted C2-C 50 heteroaryl, substituted or unsubstituted C2-C 30 Heterocyclic alkyl, substituted or unsubstituted C1-C 30 Alkoxy, substituted or unsubstituted C6-C 30 aryloxy groups, substituted or unsubstituted C1-C 30 Alkyl thio, substituted or unsubstituted C6-C 30 Arylthio, halogen, substituted or unsubstituted amino groups and substituted or unsubstituted silyl groups, L 13 It is a single bond or selected from substituted or unsubstituted C6-C. 20 aryl and substituted or unsubstituted C2-C 20 The heteroaryl group, and k is an integer from 1 to 3, provided that when k is 2 or greater, the linking group L... 13 They are the same or different from each other.

[0086] According to one embodiment of the present invention, Ar9 of formula C can be represented by formula C-1:

[0087] [Formula C-1]

[0088]

[0089] Where R 31 To R 35 They are the same or different from each other, and are defined by R as in Equation I or II, and R 31 To R 35 Each of them may optionally bond with an adjacent substituent to form a saturated or unsaturated ring.

[0090] According to one embodiment of the present invention, the subject represented by formula C may be selected from, but is not limited to, compounds of formulas C1 to C66:

[0091]

[0092]

[0093]

[0094]

[0095] The specific structure of the organic electroluminescent device according to the present invention, the method for manufacturing the device, and the materials used for the organic layer will be described below.

[0096] First, an anode material is coated onto a substrate to form an anode. The substrate can be any substrate used in general electroluminescent devices. The substrate is preferably an organic substrate or a transparent plastic substrate with excellent transparency, surface smoothness, ease of handling, and water resistance. Highly transparent and conductive metal oxides such as indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), or zinc oxide (ZnO) are used as the anode material.

[0097] Hole injection material is coated onto the anode by vacuum thermal evaporation or spin coating to form a hole injection layer. Then, hole transport material is coated onto the hole injection layer by vacuum thermal evaporation or spin coating to form a hole transport layer.

[0098] There are no specific limitations on the hole injection material, as long as it is commonly used in the art. Specific examples of such materials include 4,4',4”-tris(2-naphthylphenyl-phenylamino)triphenylamine (2-TNATA), N,N'-di(1-naphthyl)-N,N'-diphenylbenzidine (NPD), N,N'-diphenyl-N,N'-bis(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine (TPD), N,N'-diphenyl-N,N'-bis(4-(phenyl-m-tolylamino)phenyl]biphenyl-4,4'-diamine (DNTPD), and 1,4,5,8,9,11-hexaazabenzophenanthrenehexanitrile (HAT-CN).

[0099] There are no specific limitations on the hole transport material, as long as it is commonly used in the art. Examples of such materials include N,N'-bis(3-methylphenyl)-N,N'-diphenyl-(1,1-biphenyl)-4,4'-diamine (TPD) and N,N'-bis(naphthyl-1-yl)-N,N'-diphenylbenzidine (α-NPD).

[0100] Subsequently, a hole-assist layer and a light-emitting layer are sequentially formed on the hole transport layer. A hole-blocking layer can optionally be formed on the light-emitting layer by vacuum thermal evaporation or spin coating. The hole-blocking layer is formed as a thin film and blocks holes from passing through the organic light-emitting layer into the cathode. This function of the hole-blocking layer prevents degradation of the device's lifetime and efficiency. Materials with very low highest occupied molecular orbital (HOMO) energy levels are used for the hole-blocking layer. There are no particular limitations on the hole-blocking material, as long as it can transport electrons and has a higher ionization potential than the light-emitting compound. Representative examples of suitable hole-blocking materials include BAlq, BCP, and TPBI.

[0101] Examples of materials used for hole blocking layers include, but are not limited to, BAlq, BCP, Bphen, TPBI, NTAZ, BeBq2, OXD-7, and Liq.

[0102] An electron transport layer is deposited on a hole-blocking layer by vacuum thermal evaporation or spin coating, and an electron injection layer is formed on top of it. A cathode metal is then deposited on the electron injection layer by vacuum thermal evaporation to form a cathode, thus completing the fabrication of the organic electroluminescent device.

[0103] For example, lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), or magnesium-silver (Mg-Ag) can be used as the metal for forming the cathode. The organic electroluminescent device can be a top-emitting type. In this case, a transmissive material such as ITO or IZO can be used to form the cathode.

[0104] The material used in the electron transport layer serves to stably transport electrons injected from the cathode. The electron transport material can be any material known in the art, and examples include, but are not limited to, quinoline derivatives, particularly tris(8-hydroxyquinoline)aluminum (Alq3), TAZ, Balq, bis(benzoquinoline-10-hydroxy)beryllium (Bebq2); and Diazole derivatives, such as PBD, BMD and BND.

[0105] Each of the organic layers can be formed by single-molecule deposition or solution deposition. According to single-molecule deposition, the material for each layer is vapor-deposited into a thin film under heat and vacuum or reduced pressure. According to solution deposition, the material for each layer is mixed with a suitable solvent, and then the mixture is formed into a thin film by a suitable method such as inkjet printing, roll-to-roll coating, screen printing, spraying, dip coating, or spin coating.

[0106] The organic electroluminescent device of the present invention can be used in displays or lighting systems selected from the following: flat panel displays, flexible displays, monochrome flat panel lighting systems, white flat panel lighting systems, flexible monochrome lighting systems, and flexible white lighting systems.

[0107] Invention Embodiments

[0108] The invention will be explained and illustrated in more detail with reference to the following embodiments. However, it will be apparent to those skilled in the art that these embodiments are by no means intended to limit the scope of the invention.

[0109] Synthesis Example 1. Preparation of Compound A

[0110] Synthesis Example 1-1. Synthesis of Intermediate A-1

[0111]

[0112] A-1a (50.0 g) (for synthesis, see Angewandte Chemie-International Edition, 2008, Vol. 47, #9, pp. 1726-1728), A-1b (26.8 g) (for synthesis, see European Journal of Medicinal Chemistry, 2017, Vol. 134, pp. 230-241), bis(tri-tert-butylphosphine)palladium (0) (2.23 g), sodium tert-butoxide (27.9 g), and toluene (500 mL) were placed in a reactor. The mixture was stirred under reflux for 24 hours. The reaction mixture was cooled to room temperature and water (200 mL) was added. The organic layer was extracted with ethyl acetate, concentrated under reduced pressure, and purified by silica gel column chromatography to give A-1 (15.1 g, yield 28.4%).

[0113] Chemical formula: C 24 H 19 The calculated MS (ESI) value for N2S (Pos) is 367.13, and the measured value is 367.1.

[0114] Synthesis Example 1-2. Synthesis of Intermediate A-2

[0115]

[0116] A-2a (12.0 g) (see U.S. Patent Publication No. 2020 / 395553A1 for the synthesis), A-1 (11.9 g), bis(tri-tert-butylphosphine)palladium(0) (0.33 g), sodium tert-butoxide (6.23 g), and toluene (120 mL) were placed in a reactor. The mixture was stirred under reflux for 18 hours. The reaction mixture was cooled to room temperature and water (50 mL) was added. The organic layer was extracted with ethyl acetate, concentrated under reduced pressure, and purified by silica gel column chromatography to give A-2 (17.8 g, 78.4% yield).

[0117] Chemical formula: C 44 H 31 The calculated MS (ESI) value of ClN3S2(Pos) is 700.17, and the measured value is 700.1.

[0118] Synthesis Examples 1-3. Synthesis of Compound A

[0119]

[0120] A-2 (12.0 g) and tert-butylbenzene (120 mL) were placed in a reactor, and 1.7 M tert-butyllithium (30.2 mL) was added dropwise at -60 °C. The mixture was heated to 60 °C and stirred for 2 hours. The reaction mixture was cooled to -60 °C and boron tribromide (3.3 mL) was added dropwise. The resulting mixture was warmed to room temperature and stirred for 1 hour. The mixture was cooled to 0 °C and N,N-diisopropylethylamine (6.0 mL) was added dropwise. The temperature was raised to 120 °C and stirred for 16 hours. The reaction mixture was cooled to room temperature and water (50 mL) and sodium acetate (2.8 g) were added. The organic layer was extracted with ethyl acetate, concentrated under reduced pressure, and purified by silica gel column chromatography to give compound A (2.1 g, 18.2% yield).

[0121] Chemical formula: C 44 H 29 The calculated MS (ESI) value for BN3S2(Pos) is 674.19, while the measured value is 674.1.

[0122] Synthesis Example 2. Preparation of Compound B

[0123] Synthesis Example 2-1. Synthesis of Compound B

[0124]

[0125] Compound B was synthesized from intermediate B-2 in the same manner as in Synthesis Example 1 (yield 17.9%), except that intermediate A-2a was replaced by B-1 (for synthesis, see Korean Patent Publication No. 2239994B1).

[0126] Chemical formula: C 45 H 39 The calculated MS (ESI) value for BN3S (Pos) is 664.30, while the measured value is 664.3.

[0127] Synthesis Example 3. Preparation of Compound C

[0128] Synthesis Example 3-1. Synthesis of Compound C

[0129]

[0130] Compound C was synthesized from intermediate C-2 in the same manner as in Synthesis Example 1 (yield 19.3%), except that intermediate A-2a was replaced by C-1 (for synthesis, see Korean Patent Publication No. 2020-009090158A).

[0131] Chemical formula: C 51 H 47 The calculated MS (ESI) value for BN3S (Pos) is 744.36, while the measured value is 744.3.

[0132] Synthesis Example 4. Preparation of Compound D

[0133] Synthesis Example 4-1. Synthesis of Compound D

[0134]

[0135] Compound D (yield 20.2%) was synthesized from intermediate D-3 in the same manner as in Synthesis Example 1, except that intermediate A-1a was used instead of D-1 (for synthesis, see Angewandte Chemie-International Edition, 2018, Vol. 57, #38, pp. 12380-12384).

[0136] Chemical formula: C 44 H 29 The calculated MS (ESI) value for BN3OS(Pos) is 658.21, and the measured value is 658.2.

[0137] Synthesis Example 5. Preparation of Compound E

[0138] Synthesis Example 5-1. Synthesis of Compound E

[0139]

[0140] Compound E (yield 16.7%) was synthesized from intermediate E-2 in the same manner as in Synthesis Example 1, except that intermediates A-2a and A-1 were replaced by E-1 (for synthesis, see U.S. Patent Publication No. 2020 / 172558A1) and D-2, respectively.

[0141] Chemical formula: C 44 H 29 The MS (ESI) value of BN3O2(Pos) was calculated to be 642.24, while the measured value was 642.2.

[0142] Synthesis Example 6. Preparation of Compound F

[0143] Synthesis Example 6-1. Synthesis of Intermediate F-1

[0144]

[0145] Intermediate F-1 was synthesized from intermediate A-1b in the same manner as in Synthesis Example 1 (yield 30.3%), except that intermediate A-1a was used instead of intermediate F-1a (for synthesis, see Journal of Organometallic Chemistry, 2013, Vol. 735, pp. 58-64).

[0146] Chemical formula: C 26 H 25 The calculated MS(ESI) value for N₂Si(Pos) is 393.18, while the measured value is 393.1.

[0147] Synthesis Example 6-2. Synthesis of Compound F

[0148]

[0149] Compound F (yield 24.8%) was synthesized from intermediate F-3 in the same manner as in Synthesis Example 1, except that intermediates A-2a and A-1 were replaced by F-2 (for synthesis, see U.S. Patent Publication No. 2020 / 172558A1) and F-1, respectively.

[0150] Chemical formula: C 56 H 47 The calculated MS (ESI) value for BN3SSi(Pos) is 832.34, while the measured value is 832.3.

[0151] Synthesis Example 7. Preparation of Compound G

[0152] Synthesis Example 7-1. Synthesis of Intermediate G-1

[0153]

[0154] Intermediate G-1 was synthesized from intermediate A-1b in the same manner as in Synthesis Example 1 (yield 33.1%), except that intermediate A-1a was used instead of intermediate G-1a (for synthesis, see Chemistry-A European Journal, 2010, Vol. 16, #41, pp. 12299-12302).

[0155] Chemical formula: C 24 H 19 The calculated MS (ESI) value for N₂O(Pos) is 351.15, and the measured value is 351.1.

[0156] Synthesis Example 7-2. Synthesis of Compound G

[0157]

[0158] Compound G (yield 23.0%) was synthesized from intermediate G-2 in the same manner as in Synthesis Example 1, except that intermediates A-2a and A-1 were replaced by F-2 (for synthesis, see U.S. Patent Publication No. 2020 / 172558A1) and G-1, respectively.

[0159] Chemical formula: C 54 H 41 The calculated MS (ESI) value for BN3OS(Pos) is 790.31, and the measured value is 790.3.

[0160] Synthesis Example 8. Preparation of Compound H

[0161] Synthesis Example 8-1. Synthesis of Intermediate H-1

[0162]

[0163] Intermediate H-1 was synthesized from intermediate H-1b in the same manner as in Synthesis Example 1 (yield 17.1%), except that intermediates A-1a and A-1b were replaced by H-1a (for synthesis, see Cell Chemical Biology, 2020, Vol. 27, #8, pp. 1063-1072) and H-1b, respectively.

[0164] Chemical formula: C 58 H 51 The calculated MS (ESI) value for BN3S (Pos) is 832.40, and the measured value is 832.4.

[0165] combine Example 8-2. Synthesis of compound H

[0166]

[0167] Compound H was synthesized from intermediate H-3 in the same manner as in Synthesis Example 1 (yield 17.9%), except that intermediates A-2a and A-1 were replaced by H-2 (for synthesis, see U.S. Patent Publication No. 2020 / 172558A1) and H-1, respectively.

[0168] Chemical formula: C 64 H 54 The calculated MS (ESI) value for BN4S (Pos) is 921.42, and the measured value is 921.4.

[0169] Synthesis Example 9. Preparation of Compound I

[0170] Synthesis Example 9-1. Synthesis of Compound I

[0171]

[0172] Compound I was synthesized from intermediate I-2 in the same manner as in Synthesis Example 1 (yield 22.6%), except that intermediate A-2a was replaced with I-1 (for synthesis, see U.S. Patent Publication No. 2018 / 0094000A1).

[0173] Chemical formula: C 58 H 57 The calculated MS (ESI) value for BN3S (Pos) is 838.44, and the measured value is 838.4.

[0174] Synthesis Example 10. Preparation of Compound J

[0175] Synthesis Example 10-1. Synthesis of Intermediate J-1

[0176]

[0177] Intermediate J-1 was synthesized from intermediate J-1a in the same manner as in Synthesis Example 1 (yield 30.0%), except that intermediate A-1b was replaced with J-1a.

[0178] Chemical formula: C 24 H 14 The calculated MS (ESI) value for D5N2S (Pos) is 372.16, while the measured value is 372.1.

[0179] Synthesis Example 10-2. Synthesis of Intermediate J-2

[0180]

[0181] J-2a (10.0 g), J-1 (31.0 g), bis(tri-tert-butylphosphine)palladium (0) (0.43 g), sodium tert-butoxide (8.0 g), and toluene (100 mL) were placed in a reactor. The mixture was stirred under reflux for 18 hours. The reaction mixture was cooled to room temperature and water (40 mL) was added. The organic layer was extracted with ethyl acetate, concentrated under reduced pressure, and purified by silica gel column chromatography to give J-2 (29.9 g, 82.9% yield).

[0182] Chemical formula: C 55 H 30 D 10 The calculated MS (ESI) value for ClN4S2(Pos) is 865.30, while the measured value is 865.3.

[0183] Synthesis Example 10-3. Synthesis of Compound J

[0184]

[0185] Compound J was synthesized from intermediate J-2 in the same manner as in Synthesis Example 1 (yield 24.8%).

[0186] Chemical formula: C 55 H 28 D 10 The calculated MS (ESI) value for BN4S2(Pos) is 839.33, and the measured value is 839.3.

[0187] Synthesis Example 11. Preparation of Compound K

[0188] Synthesis Example 11-1. Synthesis of Intermediate K-1

[0189]

[0190] K-1a (15.0 g) (for synthesis, see Tetrahedron, 2014, Vol. 70, #32, pp. 4754-4759), K-1b (29.1 g) (for synthesis, see Chinese Patent Publication No. 106674210 and US Patent Publication No. 2020 / 172558A1), bis(tri-tert-butylphosphine)palladium(0) (0.39 g), sodium tert-butoxide (7.4 g), and toluene (150 mL) were placed in a reactor. The mixture was stirred under reflux for 12 hours. The reaction mixture was cooled to room temperature and water (60 mL) was added. The organic layer was extracted with ethyl acetate, concentrated under reduced pressure, and purified by silica gel column chromatography to give K-1 (19.3 g, 73.0% yield).

[0191] Chemical formula: C 46 H 50The calculated MS (ESI) value for Cl₂N(Pos) is 686.33, while the measured value is 686.3.

[0192] Synthesis Example 11-2. Synthesis of Intermediate K-2

[0193]

[0194] Intermediate K-2 was synthesized from intermediate K-2a in the same manner as in Synthesis Example 1 (yield 21.4%), except that intermediate A-2a was used instead of K-2a (for synthesis, see Tetrahedron Letters, 2018, Vol. 59, #22, pp. 2145-2149).

[0195] Chemical formula: C 24 H 17 The calculated MS (ESI) value for N2S (Pos) is 365.11, and the measured value is 365.1.

[0196] Synthesis Example 11-3. Synthesis of Intermediate K-3

[0197]

[0198] Intermediate K-3 was synthesized from intermediate K-1 in the same manner as in Synthesis Example 1 (yield 79.5%).

[0199] Chemical formula: C 70 H 65 The calculated MS (ESI) value of ClN3S(Pos) is 1014.46, and the measured value is 1014.4.

[0200] Synthesis Example 11-4. Synthesis of Compound K

[0201]

[0202] Compound K was synthesized from intermediate K-3 in the same manner as in Synthesis Example 1 (yield 19.5%).

[0203] Chemical formula: C 70 H 63 The calculated MS (ESI) value for BN3S(Pos) is 988.49, and the measured value is 988.4.

[0204] Synthesis Example 12. Preparation of Compound L

[0205] Synthesis Example 12-1. Synthesis of Intermediate L-1

[0206]

[0207] Intermediate L-1 was synthesized from intermediates L-1a and F-1a in the same manner as in Synthesis Example 1 (for synthesis, see Tetrahedron, 2019, Vol. 75, #6, pp. 721-731) (yield 28.9%).

[0208] Chemical formula: C 34 H 29 The calculated MS(ESI) value for N₂Si(Pos) is 493.21, and the measured value is 493.2.

[0209] combine Example 12-2. Synthesis of intermediate L-2

[0210]

[0211] Intermediate L-2 was synthesized from intermediate L-2a (for synthesis, see U.S. Patent Publication No. 2020 / 172558A1) and L-1 in the same manner as in Synthesis Example 1 (yield 81.8%).

[0212] Chemical formula: C 78 H 74 The MS (ESI) value of Cl4Si(Pos) is calculated to be 1129.54, and the measured value is 1129.5.

[0213] Synthesis Example 12-3. Synthesis of Compound L

[0214]

[0215] Compound L was synthesized from intermediate L-2 in the same manner as in Synthesis Example 1 (yield 23.8%).

[0216] Chemical formula: C 78 H 71 The calculated MS(ESI) value for BN4Si(Pos) is 1103.56, and the measured value is 1103.5.

[0217] Synthesis Example 13. Preparation of Compound M

[0218] Synthesis Example 13-1. Synthesis of Intermediate M-1

[0219]

[0220] M-1a (23.0 g) (for synthesis, see Chinese Patent Publication No. 111303149A), M-1b (16.6 g) (for synthesis, see Angewandte Chemie-International Edition, 2015, Vol. 54, #51, pp. 15385-15389), tris(dibenzylacetone)dipalladium(0) (1.34 g), bis(diphenylphosphine)-1,1'-binaphthyl (0.91 g), sodium tert-butoxide (14.1 g), and toluene (230 mL) were placed in a reactor. The mixture was stirred under reflux for 18 hours. The reaction mixture was cooled to room temperature and water (100 mL) was added. The organic layer was then separated and purified by silica gel column chromatography to give M-1 (28.1 g, yield 83.6%).

[0221] Chemical formula: C 33 H 32 The calculated MS(ESI) value for NO(Pos) is 458.25, and the measured value is 458.2.

[0222] Synthesis Example 13-2. Synthesis of Intermediate M-2

[0223]

[0224] Compound M-2 was synthesized from intermediates M-1 and M-2a in the same manner as in Synthesis Example 11 (yield 42.7%).

[0225] Chemical formula: C 39 H 34 The MS (ESI) calculated value of Cl₂NO(Pos) is 602.20, and the measured value is 602.2.

[0226] Synthesis Example 13-3. Synthesis of Intermediate M-3

[0227]

[0228] Intermediate M-3 was synthesized from intermediate M-3a in the same manner as in Synthesis Example 1 (yield 25.7%), except that intermediate A-1b was replaced with M-3a (for synthesis, see Tetrahedron, 2019, Vol. 75, #6, pp. 721-731).

[0229] Chemical formula: C 30 H 23 The calculated MS(ESI) value for N2S(Pos) is 443.16, and the measured value is 443.1.

[0230] Synthesis Example 13-4. Synthesis of Intermediate M-4

[0231]

[0232] Intermediate M-4 was synthesized from intermediates M-2 and M-3 in the same manner as in Synthesis Example 1 (yield 80.0%).

[0233] Chemical formula: C 69 H 55 The calculated MS (ESI) value of ClN3OS(Pos) is 1008.38, and the measured value is 1008.3.

[0234] Synthesis Example 13-5. Synthesis of Compound M

[0235]

[0236] Compound M was synthesized from intermediate M-4 in the same manner as in Synthesis Example 1 (yield 22.3%).

[0237] Chemical formula: C 69 H 53 The calculated MS (ESI) value for BN3OS(Pos) is 982.40, and the measured value is 982.4.

[0238] Examples 1 to 10: Fabrication of Organic Electroluminescent Devices

[0239] The ITO glass was patterned to have a 2mm × 2mm luminescent area, followed by cleaning. After the cleaned ITO glass was installed in the vacuum chamber, the base pressure was adjusted to 1 × 10⁻⁶. -7 Torr. 4,4',4”-Tris[2-naphthyl(phenyl)amino]triphenylamine (2-TNATA) and compounds represented by formula G This sequence is followed by deposition on ITO. A mixture of the main component, represented by BH1, and the compounds of the present invention shown in Table 1, in a weight ratio of 98:2, is used to form... A thick luminescent layer. Subsequently, a mixture of the compound represented by formula E-1 and the compound represented by formula E-2 in a 1:1 ratio is used to form a luminescent layer. A thick electron transport layer. A compound represented by formula E-1 is used to form the electron transport layer. A thick electron-injected layer. Al is used to form on the electron-injected layer. A thick Al electrode was used to fabricate the organic electroluminescent device. The luminescence characteristics of the organic electroluminescent device were measured at 0.4 mA.

[0240]

[0241] Comparative Examples 1 and 2

[0242] Organic electroluminescent devices (Comparative Example 1) were manufactured in the same manner as in Examples 1 to 10, except that BD1 was used as the dopant compound instead of the compound of the present invention. Organic electroluminescent devices (Comparative Example 2) were manufactured in the same manner as in Examples 1 to 10, except that BH2 was used as the host compound and BD1 was used as the dopant compound instead of the compound of the present invention. The luminescence characteristics of the organic electroluminescent devices were measured at 0.4 mA. The structures of BH1, BH2, and BD1 are as follows:

[0243]

[0244] The voltage, external quantum efficiency, and lifetime of the organic electroluminescent devices of Examples 1 to 10 and Comparative Examples 1 to 2 were measured. The results are shown in Table 1.

[0245] [Table 1]

[0246]

[0247] As can be seen from the results in Table 1, compared with the devices of Comparative Examples 1 to 2 of BD1, which use structural features that contrast with those of the compounds of the present invention, the organic electroluminescent devices of Examples 1 to 10, each using compounds of Formula I or Formula II as dopant compounds to form the light-emitting layer, exhibit significantly improved efficiency and lifetime characteristics. These results lead to the conclusion that the use of the compounds of the present invention makes organic electroluminescent devices highly efficient and durable.

[0248] Industrial applicability

[0249] The polycyclic aromatic derivatives of this invention can be used in the organic layers of organic electroluminescent devices to achieve high efficiency and long lifespan. Therefore, the polycyclic aromatic derivatives of this invention can find useful industrial applications in various displays (including flat panel displays and flexible displays) and lighting systems (including monochrome flat panel lighting systems, white flat panel lighting systems, flexible monochrome lighting systems, and flexible white lighting systems).

Claims

1. An organic compound represented by formula I or II: [Formula I] Rings A through D may be identical or different from each other, and each is independently a substituted or unsubstituted C6-C ring. 50 Monocyclic or polycyclic aromatic hydrocarbon rings, or substituted or unsubstituted C2-C... 50 Monocyclic or polycyclic aromatic heterocycles, where X is selected from B, P, P=O, P=S, and Al, and L1 and L2 are either the same or different from each other, and each is an independent single bond or selected from: -O-, -S-, and -Se-, provided that the L2 connecting rings C and D are provided in one or two forms, and that the two connecting groups L2 are the same or different from each other and optionally form a ring with rings C and D, and that Y is a single bond or selected from... -O-, -S-, and -Se-, each Z independently is CR or N, R and R1 to R 10 They may be the same as or different from each other, and each is independently selected from hydrogen, deuterium, substituted or unsubstituted C1-C. 30 Alkyl, substituted or unsubstituted C1-C 30 Alkenyl, substituted or unsubstituted C6-C 50 Aryl, substituted or unsubstituted C3-C 30 cycloalkyl, substituted or unsubstituted C 2- C 30 Heterocyclic alkyl, substituted or unsubstituted C2-C 50 heteroaryl, substituted or unsubstituted C1-C 30 Alkoxy, substituted or unsubstituted C6-C 30 aryloxy groups, substituted or unsubstituted C1-C 30 Alkyl thio, substituted or unsubstituted C5-C 30 Arylthio, substituted or unsubstituted amino, substituted or unsubstituted silyl, nitro, cyano, and halogen, provided that R1 is optionally bonded to the adjacent ring C or ring D to form an alicyclic or aromatic monocyclic or polycyclic ring, R6 to R 10 Each of the following is optionally bonded to ring A or R to form an alicyclic or aromatic monocyclic or polycyclic ring; R is optionally bonded to ring D to form an alicyclic or aromatic monocyclic or polycyclic ring; R2 and R3 are optionally linked to each other to form an alicyclic or aromatic monocyclic or polycyclic ring; R4 and R5 are optionally linked to each other to form an alicyclic or aromatic monocyclic or polycyclic ring; R7 and R8 are optionally linked to each other to form an alicyclic or aromatic monocyclic or polycyclic ring; R9 and R... 10 Optionally linked to each other to form alicyclic or aromatic monocyclic or polycyclic rings, a substituted or unsubstituted monocyclic or polycyclic non-aromatic ring optionally fused with ring A to form a fused ring, a substituted or unsubstituted monocyclic or polycyclic non-aromatic ring optionally fused with ring B to form a fused ring, a substituted or unsubstituted monocyclic or polycyclic non-aromatic ring optionally fused with ring C to form a fused ring, a substituted or unsubstituted monocyclic or polycyclic non-aromatic ring optionally fused with ring D to form a fused ring, and rings A and B optionally linked to each other. [Formula II] Rings A through F may be identical or different from each other, and each is independently a substituted or unsubstituted C6-C ring. 50 Monocyclic or polycyclic aromatic hydrocarbon rings, or substituted or unsubstituted C2-C... 50 Monocyclic or polycyclic aromatic heterocycles, where X is selected from B, P, P=O, P=S, and Al, and L1 to L4 are identical or different from each other, and each is an independent single bond or selected from: -O-, -S-, and -Se-, provided that L2 connecting rings C and D is provided in one or two forms, and the two connecting groups L2 are identical or different from each other and optionally form a ring with rings C and D; and L3 connecting rings E and F is provided in one or two forms, and the two connecting groups L3 are identical or different from each other and optionally form a ring with rings E and F; each Z is independently CR or N; R and R1 to R5 are identical or different from each other and are each independently selected from hydrogen, deuterium, substituted or unsubstituted C1-C. 30 Alkyl, substituted or unsubstituted C1-C 30 Alkenyl, substituted or unsubstituted C6-C 50 Aryl, substituted or unsubstituted C3-C 30 cycloalkyl, substituted or unsubstituted C2-C 30 Heterocyclic alkyl, substituted or unsubstituted C2-C 50 heteroaryl, substituted or unsubstituted C1-C 30 Alkoxy, substituted or unsubstituted C6-C 30 aryloxy groups, substituted or unsubstituted C1-C 30 Alkyl thio, substituted or unsubstituted C5-C 30 The composition includes an arylthio group, a substituted or unsubstituted amino group, a substituted or unsubstituted silyl group, a nitro group, a cyano group, and a halogen, provided that R1 is optionally bonded to an adjacent ring C, ring D, ring E, or ring F to form an alicyclic or aromatic monocyclic or polycyclic ring; R is optionally bonded to ring D or ring E to form an alicyclic or aromatic monocyclic or polycyclic ring; R2 and R3 are optionally linked to each other to form an alicyclic or aromatic monocyclic or polycyclic ring; R4 and R5 are optionally linked to each other to form an alicyclic or aromatic monocyclic or polycyclic ring; and a substituted or unsubstituted monocyclic or polycyclic non-aromatic ring is optionally bonded to... Ring A is fused to form a fused ring; a substituted or unsubstituted monocyclic or polycyclic nonaromatic ring is optionally fused with ring B to form a fused ring; a substituted or unsubstituted monocyclic or polycyclic nonaromatic ring is optionally fused with ring C to form a fused ring; a substituted or unsubstituted monocyclic or polycyclic nonaromatic ring is optionally fused with ring D to form a fused ring; a substituted or unsubstituted monocyclic or polycyclic nonaromatic ring is optionally fused with ring E to form a fused ring; a substituted or unsubstituted monocyclic or polycyclic nonaromatic ring is optionally fused with ring F to form a fused ring; and rings A and B are optionally connected to each other.

2. The organic compound according to claim 1, wherein the organic compound is represented by formula I-1, formula II-1, formula II-2 or formula II-3: [Formula I-1] [Formula II-1] [Formula II-2] [Formula II-3] 3. The organic compound according to claim 1, wherein the organic compound is selected from the following compounds:

4. An organic electroluminescent device comprising a first electrode, a second electrode, and one or more organic layers between the first electrode and the second electrode, wherein one of the organic layers comprises an organic compound represented by formula I or formula II according to claim 1.

5. The organic electroluminescent device according to claim 4, wherein the organic layer comprises an electron injection layer, an electron transport layer, a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, and / or a light-emitting layer, wherein at least one of them comprises the organic compound represented by Formula I or Formula II.

6. The organic electroluminescent device according to claim 5, wherein the light-emitting layer is composed of a host and the compound represented by formula I or formula II as a dopant.

7. The organic electroluminescent device according to claim 6, wherein the main body is an anthracene derivative represented by formula C: [Formula C] Where R 21 To R 28 Whether they are the same or different from each other, and as defined by R in Equation I or II, Ar9 and Ar 10 They may be the same as or different from each other, and each is independently selected from hydrogen, deuterium, substituted or unsubstituted C1-C. 30 Alkyl, substituted or unsubstituted C6-C 50 Aryl, substituted or unsubstituted C2-C 30 Alkenyl, substituted or unsubstituted C2-C 20 Alkyne group, substituted or unsubstituted C3-C 30 cycloalkyl, substituted or unsubstituted C5-C 30 Cycloalkenyl, substituted or unsubstituted C2-C 50 heteroaryl, substituted or unsubstituted C2-C 30 Heterocyclic alkyl, substituted or unsubstituted C1-C 30 Alkoxy, substituted or unsubstituted C6-C 30 aryloxy groups, substituted or unsubstituted C1-C 30 Alkyl thio, substituted or unsubstituted C6-C 30 Arylthio, halogen, substituted or unsubstituted amino groups and substituted or unsubstituted silyl groups, L 13 It is a single bond or selected from substituted or unsubstituted C6-C. 20 aryl and substituted or unsubstituted C2-C 20 The heteroaryl group, and k is an integer from 1 to 3, provided that when k is 2 or greater, the linking group L... 13 They are the same or different from each other.

8. The organic electroluminescent device according to claim 7, wherein Ar9 in formula C is represented by formula C-1: [Formula C-1] Where R 31 To R 35 They are the same or different from each other, and are defined by R as in Equation I or II, and R 31 To R 35 Each of them may optionally bond with an adjacent substituent to form a saturated or unsaturated ring.

9. The organic electroluminescent device according to claim 7, wherein the anthracene derivative represented by formula C is selected from compounds of formulas C1 to C66:

10. The organic electroluminescent device according to claim 5, wherein one or more of the layers are formed by deposition or solution processing.

11. The organic electroluminescent device according to claim 4, wherein the organic electroluminescent device is used for a display or lighting system, the display or the lighting system being selected from flat panel displays, flexible displays, monochrome flat panel lighting systems, white flat panel lighting systems, flexible monochrome lighting systems and flexible white lighting systems.

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