Polycyclic aromatic derivative compounds and organic light-emitting elements using them

Abstract

This invention relates to polycyclic aromatic derivative compounds that can be used in various organic material layers in organic light-emitting elements, and organic light-emitting elements comprising said polycyclic aromatic derivative compounds, and highly efficient and long-lifetime organic light-emitting elements that have significantly improved luminous efficiency by employing said polycyclic aromatic compounds as dopant compounds in the light-emitting layer and using anthracene derivatives with specific structures as host compounds.

Description

Technical Field

[0001] This invention relates to polycyclic aromatic derivative compounds and efficient and long-life organic light-emitting devices using the same, which have significantly improved luminous efficiency. Background Technology

[0002] Organic light-emitting devices (OLEDs) are self-emissive devices that emit light when energy is released from excitons, which are formed by the recombination of electrons injected from an electron injection electrode (cathode) and holes injected from a hole injection electrode (anode) in the light-emitting layer. Such OLEDs have attracted considerable attention as a next-generation light source due to their advantages, such as low driving voltage, high brightness, wide viewing angle, and fast response speed, making them suitable for full-color flat panel displays.

[0003] To enable organic light-emitting devices (OLEDs) to exhibit these properties, the structure of the organic layers within the OLED should be optimized, and the materials constituting each organic layer—namely, hole injection materials, hole transport materials, luminescent materials, electron transport materials, electron injection materials, or electron blocking materials—should be based on stable and efficient compositions. However, there is an ongoing need to develop organic layer structures and corresponding materials for stable and efficient OLEDs.

[0004] Furthermore, in addition to recent research on improving the characteristics of organic light-emitting devices by modifying the properties of individual organic layer materials, techniques for improving color purity and increasing luminous efficiency by optimizing the optical thickness between the anode and cathode are considered important factors in improving performance. As an example of this method, using a capping layer for the electrodes can achieve the desired luminous efficiency and excellent color purity.

[0005] Therefore, there is a continuous need to develop structures for organic light-emitting devices that can improve their light-emitting properties, as well as to develop new materials to support these structures. Summary of the Invention

[0006] Technical issues

[0007] Therefore, the present invention was made in view of the above problems, and one object of the present invention is to provide an organic light-emitting compound that can be used in an organic layer of a device to realize an efficient organic light-emitting device, and an organic light-emitting device comprising the thereof.

[0008] Technical solution

[0009] According to the present invention, the above and other objectives can be achieved by providing compounds having organic light-emitting compounds represented by the following [Formula A] or [Formula B].

[0010]

[0011] More specific structures of [Formula A] and [Formula B], the definition of Q1 to Q2, Y1 to Y6, X and Y, and specific polycyclic aromatic compounds represented by [Formula A] and [Formula B] according to the invention will be described later.

[0012] According to another aspect of the invention, an organic light-emitting device is provided, comprising a first electrode, a second electrode facing the first electrode, and an organic layer between the first electrode and the second electrode, wherein the organic layer comprises at least one of polycyclic aromatic compounds represented by [Formula A] and [Formula B].

[0013] Beneficial effects

[0014] The polycyclic aromatic compounds of the present invention can be used in the organic layer of a device to achieve a highly efficient and long-life organic light-emitting device. Attached Figure Description

[0015] Figure 1 This is a representative diagram illustrating the structure of the aromatic derivative compound according to the present invention. Detailed Implementation

[0016] The invention will now be described in detail with reference to the accompanying drawings.

[0017] This invention relates to polycyclic aromatic derivative compounds contained in organic light-emitting devices, represented by the following [Formula A] or [Formula B], and enables the realization of highly efficient organic light-emitting devices with significantly improved lifetimes.

[0018]

[0019]

[0020] in

[0021] Q1 and Q2 may be the same as or different from each other, and each independently represents a substituted or unsubstituted aromatic C6 to C50 hydrocarbon ring or a substituted or unsubstituted C2 to C50 aromatic heterocycle;

[0022] Y and Y1 through Y6 are each independently selected from N-R1, CR2R3, O, S, Se, and SiR4R5, provided that each Y and Y1 through Y6 is the same as or different from each other, and the dashed lines, according to the constraints of Y1 through Y6, indicate single or double bonds.

[0023] X is selected from B, P, and P=O. In a preferred embodiment of the present invention, X is B, and based on the structure of a polycyclic aromatic derivative compound containing boron (B), a highly efficient and long-lifetime organic light-emitting device can be realized.

[0024] R1 to R5 may be the same as or different from each other and are each independently selected from hydrogen, deuterium, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C50 aryl, substituted or unsubstituted C3 to C30 cycloalkyl, substituted or unsubstituted C2 to C50 heteroaryl, substituted or unsubstituted C1 to C30 alkoxy, substituted or unsubstituted C6 to C30 aryloxy, substituted or unsubstituted C1 to C30 alkylthio, substituted or unsubstituted C5 to C30 arylthio, substituted or unsubstituted C1 to C30 alkylamino, substituted or unsubstituted C5 to C30 arylamino, substituted or unsubstituted C1 to C30 alkylsilyl, substituted or unsubstituted C5 to C30 arylsilyl, nitro, cyano, and halogen groups.

[0025] Furthermore, R1 to R5 can be bonded to each other or can each be connected to adjacent substituents to further form alicyclic or aromatic monocyclic or polycyclic rings, and can be bonded to Q1 to Q2 rings to further form alicyclic or aromatic rings or polycyclic rings.

[0026] Furthermore, the substituents of Q1 to Q2 can bond with adjacent Y to further form alicyclic or aromatic monocyclic or polycyclic compounds.

[0027] Examples of its specific structure can be identified from the specific compounds according to the invention described later.

[0028] According to one embodiment of the present invention, framework structures such as [Formula A-1] to [Formula B-1] can be formed, various polycyclic aromatic framework structures can be formed, and efficient and long-life organic light-emitting devices can be obtained by satisfying various organic material layers based thereon.

[0029]

[0030] in

[0031] Z is CR or N, where R is selected from hydrogen, deuterium, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C50 aryl, substituted or unsubstituted C3 to C30 cycloalkyl, substituted or unsubstituted C2 to C50 heteroaryl, substituted or unsubstituted C1 to C30 alkoxy, substituted or unsubstituted C6 to C30 aryloxy, substituted or unsubstituted C1 to C30 alkylthio, and substituted or unsubstituted alkylthio. Substituted or unsubstituted C5 to C30 arylthio groups, substituted or unsubstituted C1 to C30 alkylamine groups, substituted or unsubstituted C5 to C30 arylamine groups, substituted or unsubstituted C2 to C30 arylheteroarylamine groups, substituted or unsubstituted C1 to C30 alkylsilyl groups, substituted or unsubstituted C5 to C30 arylsilyl groups, nitro groups, cyano groups, and halogens (provided that each Z and R is the same or different from each other).

[0032] According to one embodiment of the present invention, all Z can be CR, and at least one of Z can be N to satisfy the desired conditions of various organic material layers of organic light-emitting devices.

[0033] R can be bonded to each other, or each can be connected to an adjacent substituent to form an alicyclic or aromatic monocyclic or polycyclic ring, and the carbon atom of the formed alicyclic or aromatic monocyclic or polycyclic ring can be substituted by at least one heteroatom selected from N, S and O.

[0034] R can bond with Y to further form alicyclic or aromatic monocyclic or polycyclic compounds.

[0035] X, Y, and Y1 to Y6 are defined as in [Equation A] and [Equation B].

[0036] As used herein, the term "substituted" in the definitions of Q1 to Q2, R, and R1 to R9 in Formulas A and B means substituted with one or more of the following substituents: deuterium, cyano, halogen, hydroxyl, nitro, C1 to C2, cyano, hydroxyl, nitro, C1 to C2, hydroxyl ... 24 Alkyl, C3 to C 24 cycloalkyl, C1 to C 24 Haloalkyl, C1 to C 24 alkenyl, C1 to C 24 alkynyl group, C1 to C 24 Heteroalkyl, C1 to C 24 Heterocyclic alkyl, C6 to C 24 Aryl, C6 to C 24 arylalkyl, C2 to C 24 heteroaryl, C2 to C 24 Heteroarylalkyl, C1 to C 24 Alkoxy, C1 to C 24 Alkylamino, C1 to C 24 arylamino, C1 to C24 heteroarylamino, C1 to C 24 Alkyl silyl, C1 to C 24 Arylsilyl groups, and C1 to C 24 Aryloxy groups, or combinations thereof. As used herein, the term “unsubstituted” means that it does not have substituents.

[0037] In "substituted or unsubstituted C1 to C1" 10 Alkyl group, substituted or unsubstituted C6 to C6 30 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.

[0038] 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 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 of a benzene ring or two substituents on the same carbon atom in an alicyclic ring can be considered "adjacent" to each other.

[0039] Alkyl groups can be straight-chain or branched, and the number of carbon atoms therein is not particularly limited, but is preferably 1 to 20. Specific examples of alkyl groups 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.

[0040] The alkenyl group is intended to include both straight-chain and branched alkenyl groups, and may optionally be substituted with one or more other 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.

[0041] The alkynyl group is intended to include both straight-chain and branched alkynyl groups, and may optionally be substituted with one or more other substituents. The alkynyl group may be, for example, ethynyl or 2-propynyl, but is not limited thereto.

[0042] Cycloalkyl is intended to include both monocyclic and polycyclic cycloalkyl groups, and may optionally be substituted with one or more other substituents. As used herein, the term "polycyclic" means that the cycloalkyl group may be directly attached to or fused to one or more other cyclic groups. Other cyclic groups may be cycloalkyl, and other examples include heterocyclic, aryl, and heteroaryl groups. Cycloalkyl may specifically be, but is not limited to, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, or cyclooctyl.

[0043] Heterocyclic alkyl groups are intended to include monocyclic and polycyclic heterocyclic alkyl groups with heteroatoms such as O, S, Se, N, or Si inserted, and may optionally be substituted with one or more other substituents. As used herein, the term "polycyclic" means that the heterocyclic alkyl group may be directly attached to or fused to one or more other cyclic groups. Other cyclic groups may be heterocyclic alkyl groups, and other examples include cycloalkyl, aryl, and heteroaryl groups.

[0044] The aryl group 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, anthracene, phenanthryl, pyrene, perylene, and tetraphenyl. The compounds used include methyl, fluorenyl, acenaphthenicyl, triphenylene, and fluoranthyl, but the scope of the invention is not limited thereto.

[0045] A heterocyclic group is a heterocyclic group containing one or more heteroatoms. Examples of heterocyclic groups include, but are not limited to, thiophene, furanyl, pyrrole, imidazolyl, and triazolyl. 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.

[0046] 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. Mixed aliphatic-aromatic polycyclic rings may contain one or more heteroatoms selected from N, O, P, and S in addition to the carbon atom (C).

[0047] Alkoxy groups can specifically be methoxy, ethoxy, propoxy, isobutoxy, sec-butoxy, pentoxy, isopentoxy, or hexoxy, but are not limited thereto.

[0048] The term silyl is intended to include alkyl-substituted silyl groups and aryl-substituted silyl groups. Specific examples of such silyl groups include trimethylsilyl, triethylsilyl, triphenylsilyl, trimethoxysilyl, dimethoxyphenylsilyl, diphenylmethylsilyl, diphenylvinylsilyl, methylcyclobutylsilyl, and dimethylfuranylsilyl.

[0049] The amino group can be, for example, -NH2, alkylamino, and arylamino. An arylamino is an aryl-substituted amino group, and an alkylamino is an alkyl-substituted amino group. Examples of arylamino groups include substituted or unsubstituted monoarylamino groups, substituted or unsubstituted diarylamino groups, and substituted or unsubstituted triarylamino groups. The aryl moiety in an arylamino group can be a monocyclic aryl or a polycyclic aryl. An arylamino group can contain two or more aryl moieties. In this case, the aryl moieties can be monocyclic or polycyclic aryl. Alternatively, the aryl moieties can consist of both monocyclic and polycyclic aryl moieties. The aryl moieties in an arylamino group can be selected from those exemplified above.

[0050] The aryl moiety in aryloxy and arylthio groups is the same as that described above for 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 thereto.

[0051] The halogen group can be, for example, fluorine, chlorine, bromine or iodine.

[0052] More specifically, the polycyclic aromatic derivative compounds represented by [Formula A] or [Formula B] according to the present invention may be selected from [Compound 1] to [Compound 117], from which specific substituents can be clearly identified, and these compounds should not be construed as limiting the scope of [Formula A] or [Formula B] according to the present invention.

[0053]

[0054]

[0055]

[0056]

[0057]

[0058]

[0059]

[0060]

[0061]

[0062]

[0063] As can be seen from the specific compounds, a polycyclic aromatic structure containing B, P, P=O, etc., is formed, and substituents are introduced therein, thereby synthesizing organic light-emitting materials with the inherent properties of the substituents. For example, by introducing substituents of materials used in the manufacture of organic light-emitting devices for hole injection layers, hole transport layers, light-emitting layers, electron transport layers, electron injection layers, electron blocking layers, hole blocking layers, etc., into the structure, organic light-emitting materials that meet the requirements of the corresponding organic layers can be produced. Based on this, highly efficient organic light-emitting devices can be realized. Furthermore, the compounds according to the present invention can be used alone or in combination with other compounds as materials for different organic layers, or can be used as capping layers (CPLs).

[0064] Furthermore, in another aspect, the present invention relates to an organic light-emitting device comprising a first electrode, a second electrode, and at least one organic layer between the first electrode and the second electrode, wherein the organic layer comprises at least one organic light-emitting compound represented by [Formula A] or [Formula B] according to the present invention.

[0065] That is, an organic light-emitting device according to one embodiment of the present invention may have a structure including a first electrode, a second electrode and at least one organic layer disposed therebetween, and the organic light-emitting device may be manufactured using conventional methods and materials for manufacturing devices, except that an organic light-emitting compound according to [Formula A] or [Formula B] of the present invention is used in the organic layer of the device.

[0066] The organic layer of the organic light-emitting device according to the present invention can have a single-layer structure or a multilayer structure in which two or more organic layers are stacked. 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, an electron injection layer, etc. However, the structure of the organic layer is not limited to this, and it can include fewer or more organic layers. Preferred organic material layer structures of the organic light-emitting device according to the present invention will be described in more detail in the examples given later.

[0067] Furthermore, an organic light-emitting device according to one embodiment of the present invention includes a substrate, a first electrode (anode), an organic material layer, a second electrode (cathode), and a capping layer, wherein the capping layer is formed on top of the second electrode (top emission).

[0068] In the top-emission mode, light formed in the light-emitting layer is emitted toward the cathode, and the light emitted toward the cathode passes through a capping layer (CPL) with a relatively high refractive index formed from the compound according to the invention. At this point, the wavelength is amplified, and thus the luminous efficiency is improved.

[0069] An embodiment of the organic light-emitting device according to the present invention will be described in more detail below.

[0070] The organic light-emitting device according to the present invention includes an anode, a hole transport layer, a light-emitting layer, an electron transport layer, and a cathode. If necessary, a hole injection layer may be included between the anode and the hole transport layer, and an electron injection layer may be included between the electron transport layer and the cathode. One or two intermediate layers may also be included, as well as a hole blocking layer or an electron blocking layer. As described above, depending on the characteristics of the organic light-emitting device, the organic light-emitting device may also include organic layers with various functions, such as the aforementioned capping layer.

[0071] As a more preferred embodiment of the present invention, the organic layer between the first electrode and the second electrode includes a light-emitting layer, the light-emitting layer comprising a host and a dopant, and the compound represented by [Formula A] or [Formula B] according to the present invention is included in the light-emitting layer as a dopant.

[0072] The light-emitting layer of the organic electroluminescent device according to the present invention comprises an anthracene derivative represented by formula C as the host compound:

[0073]

[0074] Where R 21 To R 28 They may be the same or different from each other and, as in equations A-1 or A-2, R1 to R2 13 As specified, 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 to C2. 30 Alkyl, substituted or unsubstituted C6 to C 50 Aryl, substituted or unsubstituted C2 to C 30 Alkenyl, substituted or unsubstituted C2 to C 20 Alkyne group, substituted or unsubstituted C3 to C 30 cycloalkyl, substituted or unsubstituted C5 to C6 30 Cycloalkenyl, substituted or unsubstituted C2 to C 50 heteroaryl, substituted or unsubstituted C2 to C 30 Heterocyclic alkyl groups, substituted or unsubstituted C1 to C2 30 Alkoxy, substituted or unsubstituted C6 to C 30 aryloxy groups, substituted or unsubstituted C1 to C2 groups 30 Alkyl thio, substituted or unsubstituted C6 to C 30 arylthio, substituted or unsubstituted C1 to C2 30 Alkylamine, substituted or unsubstituted C6 to C 30 arylamine, substituted or unsubstituted C1 to C2 30Alkyl silyl groups, and substituted or unsubstituted C6 to C6 groups. 30 Arylsilyl, L 13 It is a single bond or selected from substituted or unsubstituted C6 to C6 bonds. 20 aryl and substituted or unsubstituted C2 to C3 20 Hypoaryl groups, preferably single bonds or substituted or unsubstituted C6 to C6 bonds. 20 arylene, 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.

[0075] Ar9 in equation C is represented by equation C-1:

[0076]

[0077] Where R 31 To R 35 They may be the same or different from each other and, as in equations A-1 or A-2, R1 to R2 13 Limited by, and R 31 To R 35 Each can optionally bond with an adjacent substituent to form a saturated or unsaturated ring.

[0078] The compound of formula C used in the organic electroluminescent device of the present invention can be specifically selected from compounds of formulas C1 to C48:

[0079]

[0080]

[0081]

[0082] The organic electroluminescent device of the present invention may further include a hole transport layer and an electron blocking layer, each of which may contain a compound represented by formula D:

[0083]

[0084] Where R 41 To R 43 They may be the same as or different from each other, and each is independently selected from hydrogen, deuterium, substituted or unsubstituted C1 to C2. 20 Alkyl, substituted or unsubstituted C6 to C 50 Aryl, substituted or unsubstituted C7 to C 50 Arylalkyl, substituted or unsubstituted C3 to C4 30 cycloalkyl, substituted or unsubstituted C1 to C 30 Alkyl silyl, substituted or unsubstituted C6 to C 30Arylsilanes and halogens, L 31 To L 34 They may be the same or different from each other, and each is independently a single bond or selected from substituted or unsubstituted C6 to C6 bonds. 50 aryl and substituted or unsubstituted C2 to C3 50 Aryl esters 31 To Ar 34 They may be the same as or different from each other, and each is independently selected from substituted or unsubstituted C6 to C6. 50 Aryl groups and substituted or unsubstituted C2 to C3 groups 50 Heteroaryl, n is an integer from 0 to 4, provided that when n is 2 or greater, it contains R. 43 The aromatic rings are either identical or distinct, and m1 to m3 are integers from 0 to 4, provided that both m1 and m3 are 2 or greater. 41 R 42 and R 43 The groups may be the same or different from each other, and the hydrogen or deuterium atom is not attached to the R of the aromatic ring. 41 To R 43 Carbon atom bonding.

[0085] In equation D, Ar 31 To Ar 34 At least one of them is represented by E:

[0086]

[0087] Where R 51 To R 54 They may be the same as or different from each other, and each is independently selected from hydrogen, deuterium, substituted or unsubstituted C1 to C2. 30 Alkyl, substituted or unsubstituted C6 to C 50 Aryl, substituted or unsubstituted C2 to C 30 Alkenyl, substituted or unsubstituted C2 to C 20 Alkyne group, substituted or unsubstituted C3 to C 30 cycloalkyl, substituted or unsubstituted C5 to C6 30 Cycloalkenyl, substituted or unsubstituted C2 to C 50 heteroaryl, substituted or unsubstituted C2 to C 30 Heterocyclic alkyl groups, substituted or unsubstituted C1 to C2 30 Alkoxy, substituted or unsubstituted C6 to C 30 aryloxy groups, substituted or unsubstituted C1 to C2 groups 30 Alkyl thio, substituted or unsubstituted C5 to C6 30 arylthio, substituted or unsubstituted C1 to C2 30Alkylamine, substituted or unsubstituted C5 to C6 30 arylamine, substituted or unsubstituted C1 to C2 30 Alkyl silyl, substituted or unsubstituted C5 to C6 30 Arylsilyl, nitro, cyano, and halogen, optionally linked together to form a ring, where Y is a carbon or nitrogen atom, Z is a carbon, oxygen, sulfur, or nitrogen atom, and Ar... 35 To Ar 37 They may be the same as or different from each other, and each is independently selected from substituted or unsubstituted C5 to C6. 50 Aryl groups and substituted or unsubstituted C3 to C4 groups 50 Heteroaryl groups, without Ar if Z is an oxygen or sulfur atom. 37 If Y and Z are nitrogen atoms, then only Ar exists. 35 Ar 36 and Ar 37 One of them, if Y is a nitrogen atom and Z is a carbon atom, then there is no Ar. 36 The condition is R 51 To R 54 and Ar 35 To Ar 37 One of them is the linking group L in formula D. 31 To L 34 One of the keys is connected to a single key.

[0088] The compound of formula D used in the organic electroluminescent device of the present invention can be specifically selected from compounds of formulas D1 to D79:

[0089]

[0090]

[0091]

[0092]

[0093]

[0094] The compound of formula D used in the organic electroluminescent device of the present invention can be specifically selected from compounds of formulas D101 to D145:

[0095]

[0096]

[0097]

[0098] The organic electroluminescent device of the present invention may further include a hole transport layer and an electron blocking layer, each of which may contain a compound represented by formula F:

[0099]

[0100] Where R 61 To R 63 They may be the same as or different from each other, and each is independently selected from hydrogen, deuterium, substituted or unsubstituted C1 to C2. 30 Alkyl, substituted or unsubstituted C6 to C 50 Aryl, substituted or unsubstituted C2 to C 30 Alkenyl, substituted or unsubstituted C2 to C 20 Alkyne group, substituted or unsubstituted C3 to C 30 cycloalkyl, substituted or unsubstituted C5 to C6 30 Cycloalkenyl, substituted or unsubstituted C2 to C 50 heteroaryl, substituted or unsubstituted C2 to C 30 Heterocyclic alkyl groups, substituted or unsubstituted C1 to C2 30 Alkoxy, substituted or unsubstituted C6 to C 30 aryloxy groups, substituted or unsubstituted C1 to C2 groups 30 Alkyl thio, substituted or unsubstituted C6 to C 30 arylthio, substituted or unsubstituted C1 to C2 30 Alkylamine, substituted or unsubstituted C6 to C 30 arylamine, substituted or unsubstituted C1 to C2 30 Alkyl silyl, substituted or unsubstituted C6 to C 30 Arylsilyl, substituted or unsubstituted C1 to C 30 Alkyl germanium, substituted or unsubstituted C1 to C2 30 Arylgermanium, cyano, nitro and halogens, and Ar 51 To Ar 54 They may be the same as or different from each other, and each is independently substituted or unsubstituted C6 to C6. 40 aryl or substituted or unsubstituted C2 to C 30 Mixed aromatic compounds.

[0101] The compound of formula F used in the organic electroluminescent device of the present invention can be specifically selected from compounds of formulas F1 to F33:

[0102]

[0103]

[0104]

[0105] 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.

[0106] First, an anode material is coated onto a substrate to form the anode. The substrate can be any substrate used in general electroluminescent devices. Preferably, the substrate is an organic substrate or a transparent plastic substrate that excels in 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.

[0107] 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.

[0108] 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), and N,N'-diphenyl-N,N'-bis(4-(phenyl-m-tolylamino)phenyl)biphenyl-4,4'-diamine (DNTPD).

[0109] 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).

[0110] Subsequently, a hole-assist layer and a light-emitting layer are sequentially laminated 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 forms 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.

[0111] Examples of materials used for hole blocking layers include, but are not limited to, BAlq, BCP, Bphen, TPBI, NTAZ, BeBq2, OXD-7, and Liq.

[0112] 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 the electron transport layer. 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.

[0113] 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.

[0114] The material used in the electron transport layer serves to stably transport electrons injected from the cathode. The electron transport material can be any electron transport material known in the art, and examples include, but are not limited to, quinoline derivatives, particularly tris(8-quinoline)aluminum (Alq3), TAZ, Balq, bis(benzoquinoline-10-hydroxy)beryllium (Bebq2), ADN, and... Diazole derivatives such as PBD, BMD, and BND.

[0115] The organic layers can be formed using either single-molecule deposition or solution methods. According to single-molecule deposition, the material for each layer is vapor-deposited into a thin film under heating and vacuum or reduced pressure. According to solution methods, the material for each layer is mixed with a suitable solvent, and then the mixture is formed into a thin film using suitable methods such as inkjet printing, roll-to-roll coating, screen printing, spraying, dip coating, or spin coating.

[0116] The organic electroluminescent device of the present invention can be used in a display or lighting system selected from the following: flat panel display, flexible display, monochrome flat panel lighting system, white flat panel lighting system, flexible monochrome lighting system and flexible white lighting system.

[0117] Invention Embodiments

[0118] The invention will now be described in more detail with reference to preferred embodiments. However, it will be apparent to those skilled in the art that these embodiments are provided for illustrative purposes only and should not be construed as limiting the scope of the invention.

[0119] Synthesis Example 1. Synthesis of Compound 1

[0120] Synthesis Example 1-1. Synthesis of <Intermediate 1-a>

[0121]

[0122] In a 500 mL reactor under reflux, 25 g (103 mmol) of 2,3-dibromothiophene, 30.2 g (248 mmol) of phenylboronic acid, 42.8 g (310 mmol) of potassium carbonate, 4.8 g (4 mmol) of tetrakis(triphenylphosphine)palladium, 60 mL of water, 130 mL of toluene, and 130 mL of 1,4-dibromothiophene were added. The alkane was stirred for 12 hours. After the reaction was complete, the reaction products were separated into layers, and the organic layer was concentrated under reduced pressure. The residue was separated by chromatography to obtain 22.4 g of <intermediate 1-a> (yield 85.1%).

[0123] Synthesis Example 1-2. Synthesis of <Intermediate 1-b>

[0124]

[0125] 24 g (102 mmol) of <intermediate 1-a> and 240 mL of chloroform were added to a 500 mL reactor and stirred. The reaction product was cooled to 0 °C, and a diluted solution of 15.5 g (102 mmol) of bromine in 50 mL of chloroform was added dropwise. The mixture was then stirred at room temperature for 4 hours. After the reaction was complete, an aqueous solution of sodium thiosulfate was added, and the mixture was stirred and extracted with ethyl acetate and H₂O. The organic layer was concentrated under reduced pressure and separated by chromatography to obtain 30 g of <intermediate 1-b> (yield: 88%).

[0126] Synthesis Example 1-3. Synthesis of <Intermediate 1-c>

[0127]

[0128] In a 100 mL reactor, 4.5 g (16 mmol) of 1-bromo-2,3-dichlorobenzene, 5.8 g (16 mmol) of aniline, 0.1 g (1 mmol) of palladium acetate, 3 g (32 mmol) of sodium tert-butoxide, 0.2 g (1 mmol) of bis(diphenylphosphine)-1,1'-binaphthylene, and 45 mL of toluene were stirred under reflux for 24 hours. After the reaction was complete, the filtrate was concentrated and separated by chromatography to obtain 5.2 g of <intermediate 1-c> (yield 82%).

[0129] Synthesis Example 1-4. Synthesis of <Intermediate 1-d>

[0130]

[0131] In a 500 mL reactor, 20 g (98 mmol) of intermediate 1-b, 18.4 g (98 mmol) of intermediate 1-c, 0.5 g (2 mmol) of palladium acetate, 18.9 g (196 mmol) of sodium tert-butoxide, 0.8 g (4 mmol) of tri-tert-butylphosphine, and 200 mL of toluene were stirred under reflux for 5 hours. After the reaction was complete, the filtrate was concentrated and separated by chromatography to obtain 22 g of intermediate 1-d (yield 75%).

[0132] Synthesis Examples 1-5. <Synthesis of Intermediate 1-e>

[0133]

[0134] 18.5 g of intermediate 1-e was obtained in the same manner as in synthetic examples 1-4, except that intermediate 1-d and diphenylamine were used instead of intermediates 1-b and 1-c. (Yield 74.1%)

[0135] Synthesis Examples 1-6. Synthesis of <Compound 1>

[0136]

[0137] 18.5 g (23 mmol) of <intermediate 1-e> and 190 mL of tert-butylbenzene were added to a 300 mL reactor. 42.5 mL (115 mmol) of tert-butyllithium was added dropwise at -78 °C. After the addition, the product was stirred at 60 °C for 3 hours. Pentane was then removed by purging with nitrogen. 11.3 g (46 mmol) of boron tribromide was added dropwise at -78 °C. After the addition, the mixture was stirred at room temperature for 2 hours, and 5.9 g (46 mmol) of N,N-diisopropylethylamine was added dropwise at 0 °C. After the addition, the mixture was stirred at 120 °C for 2 hours. After the reaction was complete, an aqueous solution of sodium acetate was added at room temperature and stirred. After extraction with ethyl acetate, the organic layer was concentrated and separated by column chromatography to obtain 3.4 g of <compound 1> (yield 15.7%).

[0138] MS (MALDI-TOF): m / z 578.20 [M + ]

[0139] Synthesis Example 2. Synthesis of Compound 19

[0140] Synthesis Example 2-1. Synthesis of <Intermediate 2-a>

[0141]

[0142] In a 1 L reactor, 50 g (177 mmol) of 1-bromo-3-iodobenzene, 36.2 g (389 mmol) of aniline, 1.6 g (7 mmol) of palladium acetate, 51 g (530 mmol) of sodium tert-butoxide, 4.4 g (7 mmol) of bis(diphenylphosphine)-1,1'-binaphthylene, and 500 mL of toluene were stirred under reflux for 24 hours. After the reaction was complete, the resulting product was filtered, the filtrate was concentrated, and chromatographically separated to obtain 42.5 g of <intermediate 2-a> (yield 50%).

[0143] Synthesis Example 2-2. Synthesis of <Intermediate 2-b>

[0144]

[0145] In a 250 mL reactor, 11 g (42 mmol) of intermediate 2-a, 20 g (101 mmol) of intermediate 1-b, 1 g (2 mmol) of palladium acetate, 12.2 g (127 mmol) of sodium tert-butoxide, 0.7 g (3 mmol) of tri-tert-butylphosphine, and 150 mL of toluene were stirred under reflux for 5 hours. After the reaction was complete, the product was filtered, the filtrate was concentrated, and 11 g of intermediate 2-b was obtained by chromatography (yield 65%).

[0146] Synthesis Examples 2-3. Synthesis of <Compound 19>

[0147]

[0148] 2.7 g of <Compound 19> was obtained in the same manner as in Synthetic Examples 1-6, except that <Intermediate 2-b> was used instead of <Intermediate 1-e>. (Yield 14.7%)

[0149] MS (MALDI-TOF): m / z 736.22 [M + ]

[0150] Synthesis Example 3. Synthesis of Equation 97

[0151] Synthesis Example 3-1. Synthesis of <Intermediate 3-a>

[0152]

[0153] 35.6 g of <intermediate 3-a> was obtained in the same manner as in Synthetic Examples 1-3, except that 1-bromo-2,3-dichloro-5-methylbenzene and 4-tert-butylaniline were used instead of 1-bromo-4-iodobenzene and aniline. (Yield 71.2%)

[0154] Synthesis Example 3-2. Synthesis of <Intermediate 3-b>

[0155]

[0156] In a 2 L reactor, 60.0 g (355 mmol) of diphenylamine, 100.3 g (355 mmol) of 1-bromo-3-iodobenzene, 0.8 g (4 mmol) of palladium acetate, 2 g (4 mmol) of Xantphos, 68.2 g (709 mmol) of sodium tert-butoxide, and 700 mL of toluene were stirred under reflux for 2 hours. After the reaction was complete, the resulting product was filtered at room temperature, and the filtrate was concentrated under reduced pressure and separated by chromatography to obtain 97 g of <intermediate 3-b> (yield 91.2%).

[0157] Synthesis Example 3-3. Synthesis of <Intermediate 3-c>

[0158]

[0159] 31 g of <intermediate 3-c> was obtained in the same manner as in Synthetic Examples 1-4, except that <intermediate 3-a> and <intermediate 3-b> were used instead of <intermediate 1-c> and <intermediate 1-b> (yield 77.7%).

[0160] Synthesis Example 3-4. Synthesis of <Intermediate 3-d>

[0161]

[0162] 31.6 g of intermediate 3-d was obtained in the same manner as in Synthetic Examples 1-3, except that intermediate 1-b and 4-tert-butylaniline were used instead of intermediate 1-b and 4-tert-butylaniline. (Yield 68.2%)

[0163] Synthesis Example 3-5. <Synthesis of Intermediate 3-e>

[0164]

[0165] 21 g of <intermediate 3-e> was obtained in the same manner as in Synthetic Examples 1-4, except that <intermediate 3-c> and <intermediate 3-d> were used instead of <intermediate 1-c> and <intermediate 1-b>. (Yield 67.7%)

[0166] Synthesis Examples 3-6. Synthesis of <Compound 97>

[0167]

[0168] Compound 97 (2.4) was obtained in the same manner as in Synthetic Examples 1-6, except that intermediate 3-e was used instead of intermediate 1-e. (Yield 15.4%)

[0169] MS (MALDI-TOF): m / z 871.41 [M + ]

[0170] Examples 1 to 10: Fabrication of Organic Light-Emitting Devices

[0171] The ITO glass was patterned to adjust the luminescent area to 2mm × 2mm, and then washed. The ITO glass was installed in a vacuum chamber, and the base pressure was set to 1 × 10⁻⁶. -7 Torx, and sequentially deposited DNTPD on ITO. and [Formula H] Then, a mixture of the main component [BH1] described below and the compound of the present invention (3 wt%) was deposited onto... The thickness is increased to form a light-emitting layer. Then, a mixture (1:1) of [Formula E-1] and [Formula E-2] is deposited on the light-emitting layer to a thickness of [thickness]. The thickness is such that an electron transport layer is formed, and [Equation E-1] is deposited on the electron transport layer to... The thickness is such that an electron injection layer is formed, and Al is deposited on the electron injection layer to a thickness of [missing information]. The thickness was determined. As a result, an organic light-emitting device was fabricated. The luminescence characteristics of the organic light-emitting device were measured at 0.4 mA.

[0172]

[0173]

[0174] Comparative Examples 1 to 3

[0175] The organic light-emitting device was manufactured in the same manner as in the examples above, except that [BD1] to [BD3] were used instead of the compounds used in Example 1. The luminescence characteristics of the organic light-emitting device were measured at 0.4 mA. The structures of [BD1] to [BD3] are as follows.

[0176]

[0177] The voltage, brightness, color coordinates, and lifetime of the organic light-emitting devices manufactured according to Examples 1 to 10 and Comparative Examples 1 to 3 were measured, and the results are shown in Table 1 below.

[0178] [Table 1]

[0179]

[0180]

[0181] As can be seen from Examples 1 to 10, compared with the organic light-emitting devices using Comparative Examples 1 to 3, the organic light-emitting devices containing the boron compound according to the present invention exhibit high external quantum efficiency and significantly improved lifetime.

[0182] Examples 11 to 18: Fabrication of Organic Light-Emitting Devices

[0183] The ITO glass was patterned to adjust the luminescent area to 2mm × 2mm, and then washed. The ITO glass was installed in a vacuum chamber, and the base pressure was set to 1 × 10⁻⁶. -7 Torque, and sequentially deposited 2-TNATA (4,4′,4″-tris[2-naphthyl(phenyl)amino]triphenylamine) on ITO. and hole transport layer Then, the mixture of the main component described in [Table 2] and the compound of the present invention (3% by weight) was deposited onto... The thickness is increased to form a light-emitting layer. Then, [Formula E-2] is deposited on the light-emitting layer to... The thickness is such that an electron transport layer is formed, and [Equation E-1] is deposited on the electron transport layer to... The thickness is increased to form an electron injection layer, and MgAg is deposited on the electron injection layer to a thickness of [missing information]. The thickness is then increased, and a capping layer is deposited on top of it until... The thickness was determined. As a result, an organic light-emitting device was fabricated. The luminescence characteristics of the organic light-emitting device were measured at 0.4 mA.

[0184] Compare Examples 4 and 5

[0185] Organic light-emitting devices were fabricated in the same manner as in Examples 11 to 18, except that Alq3 was used as a capping layer. The luminescence characteristics of the organic light-emitting devices were measured at 10 mA. The structure of [Alq3] is as follows:

[0186]

[0187] [Table 2]

[0188]

[0189]

[0190] As can be seen from Examples 11 to 18, compared with devices using [Alq3] compounds as a capping layer, organic light-emitting devices containing compounds according to the present invention, especially organic light-emitting devices according to the present invention, exhibit high external quantum efficiency and significantly improved lifetime.

[0191] Industrial applicability

[0192] The polycyclic aromatic derivatives of this invention can be used in the organic layers of organic electroluminescent devices to achieve high efficiency and long lifetime. Due to these advantages, organic electroluminescent devices can find useful industrial applications in a variety of displays and lighting systems, including flat panel displays, flexible displays, monochrome flat panel lighting systems, white flat panel lighting systems, flexible monochrome lighting systems, and flexible white lighting systems.

Claims

1. An organic luminescent compound represented by the following [Formula A-1], [Formula A-1] in X is B; Y is N-R1; Y1 to Y2 are each independently CR2R3; Y3 is S; The condition is that each Y is either the same as or different from the others; The condition is that Y1 and Y2 are either the same or different from each other; The dashed lines, defined by Y1 to Y3, indicate single or double bonds; Z represents CR. R1, R2, and R3 may be the same as or different from each other, and R is independently selected from hydrogen; unsubstituted methyl, ethyl, propyl, or butyl; or diphenylamino groups substituted with or unsubstituted with methyl, ethyl, propyl, or butyl. R1 is independently selected from hydrogen; or is a C6 aryl group substituted with methyl, ethyl, propyl, or butyl, or unsubstituted. R2 and R3 are each independently selected from hydrogen; or phenyl or biphenyl substituted with methyl, ethyl, propyl or butyl or unsubstituted. The condition is that each Z and R is either the same or different from each other.

2. The organic light-emitting compound according to claim 1, wherein [Formula A-1] is selected from the following compounds:

3. An organic light-emitting device, comprising: First electrode; The second electrode facing the first electrode; and An organic layer between the first electrode and the second electrode, The organic layer comprises at least one of the compounds represented by [Formula A-1] according to claim 1.

4. The organic light-emitting device according to claim 3, wherein the organic layer comprises at least one of 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 a light-emitting layer. At least one of the layers contains the organic light-emitting compound represented by [Formula A-1].

5. The organic light-emitting device according to claim 3, wherein the organic layer between the first electrode and the second electrode comprises a light-emitting layer, the light-emitting layer comprising a host and a dopant, and the compound represented by [Formula A-1] is used as a dopant.

6. The organic light-emitting device according to claim 5, wherein the light-emitting layer comprises an anthracene derivative represented by formula C as the host compound: [Formula C] Where R 21 To R 28 Whether they are the same or different and as defined for R in equation A-1, Ar9 and Ar 10 They may be the same as or different from each other, and each is independently selected from hydrogen, deuterium, and unsubstituted C1 to C2. 30 Alkyl, unsubstituted C6 to C 50 Aryl, unsubstituted C2 to C 30 Alkenyl, unsubstituted C2 to C 20 Alkyne group, or unsubstituted dibenzofuran group, L 13 It is a single bond or selected from an unsubstituted C6 aryl 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.

7. The organic light-emitting device according to claim 4, wherein one or more of the layers are formed by deposition or solution processing.

8. The organic light-emitting device according to claim 3, wherein the organic light-emitting device is used in a display or lighting system selected from: flat panel display, flexible display, monochrome flat panel lighting system, white flat panel lighting system, flexible monochrome lighting system and flexible white lighting system.

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