Compound and organic light-emitting element comprising same

Abstract

The present specification relates to a compound of chemical formula 1 capable of improving efficiency and lifespan characteristics of an organic light-emitting device, and an organic light-emitting device including an anode; a cathode; and one or more organic layers disposed between the anode and the cathode, wherein one or more of the organic layers include a compound of Chemical Formula 1.

Description

Technical Field

[0001] This application claims priority to Korean Patent Application No. 10-2024-0071395, filed on May 31, 2024, with the Korean Intellectual Property Office, the contents of which are incorporated herein by reference in their entirety.

[0002] This disclosure relates to compounds and organic light-emitting devices containing the same. Background Technology

[0003] Generally, organic light emission refers to the phenomenon of converting electrical energy into light energy using organic materials. Organic light-emitting devices (OLEDs) typically have a structure comprising an anode, a cathode, and an organic layer between them. Here, the organic layer usually has a multilayer structure composed of different materials to improve the efficiency and stability of the OLED. For example, it can consist of a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer. In the structure of an OLED, when a voltage is applied between the two electrodes, holes are injected from the anode into the organic layer, and electrons are injected from the cathode into the organic layer. When the injected holes and electrons recombine, they form excitons, and when the excitons return to the ground state, they emit light.

[0004] New materials need to be developed for organic light-emitting devices. Summary of the Invention

[0005] Technical issues

[0006] This specification provides compounds and organic light-emitting devices containing them.

[0007] Technical solution

[0008] An exemplary embodiment of this specification provides a compound of formula 1:

[0009] [Chemical Formula 1]

[0010]

[0011] In chemical formula 1,

[0012] At least one of R1 to R12 is of chemical formula 2, and the remaining R1 to R12 that are not of chemical formula 2 are the same or different, and are independently hydrogen; deuterium; substituted or unsubstituted aryl; or substituted or unsubstituted heteroaryl.

[0013] [Chemical Formula 2]

[0014]

[0015] In chemical formula 2,

[0016] Y1 is either O or S.

[0017] L1 is a direct bond; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group.

[0018] l1 is either 1 or 2, and if l1 is 2, then L1 is either the same or different.

[0019] G1 through G3 may be the same or different, and are independently hydrogen; deuterium; deuterated or unsubstituted phenyl; deuterated or unsubstituted biphenyl; deuterated or unsubstituted naphthyl; deuterated or unsubstituted phenanthryl; or deuterated or unsubstituted C 5-20 Mixed aromatics,

[0020] g1 to g3 are each an integer from 1 to 4.

[0021] If g1 is 2 or greater, then two or more G1 values ​​are the same or different.

[0022] If g2 is 2 or greater, then two or more G2 values ​​are either the same or different.

[0023] If g3 is 2 or greater, then two or more G3s are the same or different.

[0024] m is 0 or 1.

[0025] If m is 0, then g2 is an integer from 1 to 4 and g1 + g2 ≤ 7.

[0026] If m is 1, then g2 is 1 or 2 and g1 + g2 + g3 ≤ 9.

[0027] For the portion bonded to chemical formula 1, and

[0028] Chemical formula 1 contains at least one deuterium.

[0029] Furthermore, an exemplary embodiment of this specification provides an organic light-emitting device comprising: an anode; a cathode; and one or more organic layers disposed between the anode and the cathode, wherein one or more of the organic layers comprises a compound of formula 1.

[0030] Furthermore, an exemplary embodiment of this specification provides an organic light-emitting device comprising: an anode; a cathode; a first light-emitting layer disposed between the anode and the cathode; and a second light-emitting layer disposed between the first light-emitting layer and the cathode and in contact with the first light-emitting layer, wherein the first light-emitting layer comprises a compound of chemical formula 1, and the second light-emitting layer comprises a compound of chemical formula H.

[0031] [Chemical formula H]

[0032]

[0033] In the chemical formula H,

[0034] L20 and L21 may be the same or different, and are independently direct bonds; substituted or unsubstituted aryl groups; or substituted or unsubstituted divalent heterocyclic groups.

[0035] Ar20 and Ar21 may be the same or different, and are independently hydrogen; deuterium; substituted or unsubstituted aryl; or substituted or unsubstituted heterocyclic groups.

[0036] R301 is hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, and

[0037] r301 is an integer from 1 to 8, and if r301 is 2 or greater, then two or more R301 are the same or different.

[0038] Beneficial effects

[0039] The compounds described in this specification can be used as materials for the organic layer of organic light-emitting devices (OLEDs). Conventionally used anthracene-based compounds utilize triplet-triplet fusion (TTF) as their primary light-emitting mechanism. In OLEDs using anthracene-based compounds as the host of the light-emitting layer, the region where holes and electrons recombine (recombination region) corresponds to the region of light emission (light-emitting region). If a compound of Formula 1, which has a higher triplet energy than the anthracene-based compounds described in this specification, is used as the host along with a second host having a lower triplet energy, excitons are formed as holes and electrons recombine within the compound. Singlet states participate in light emission, and triplet states transfer to the second host with the lower triplet energy (Dexter energy transfer). The anthracene-based compound or the second host that has transferred to the triplet state emits light via TTF. This improves the efficiency and lifetime characteristics of the OLED. Attached Figure Description

[0040] Figures 1 to 4 An example of the structure of an organic light-emitting device according to an exemplary embodiment of this specification is shown.

[0041] Figure 5 The MS spectrum of compound A is shown.

[0042] [Detailed Description of Key Elements]

[0043] 1: Base

[0044] 2: Anode

[0045] 3: Hole injection layer

[0046] 4: Hole transport layer

[0047] 34: Hole Injection and Transport Layer

[0048] 5: Cavity blocking layer

[0049] 6: Emissive layer

[0050] 6-1: First light-emitting layer

[0051] 6-2: Second light-emitting layer

[0052] 7: Electron blocking layer

[0053] 8: Electron transport layer

[0054] 9: Electron injection layer

[0055] 10: Cathode Detailed Implementation

[0056] The contents of this disclosure will be described in more detail below.

[0057] According to an exemplary embodiment of this specification, a compound of formula 1 is a compound in which formula 2 is bonded to... The specific location of the nucleus and its bonding to chemical formula 2 and triplet energy levels of substituents (T) s 1) Higher than or equal to The triplet energy level, or a compound in which the elements are bonded to chemical formula 2 and triplet energy levels of substituents (T) s 1) lower than triplet energy levels and T s 1 and The difference between the triplet energy levels is greater than 0 eV and is 0.2 eV or less. Since the compound of Formula 1 has a higher triplet energy than conventionally used anthracene-based compounds, it transfers the triplet energy to the second host used together. This reduces triplet quenching of the compound compared to using the second host (anthracene-based compound) alone, and can improve the efficiency and lifetime characteristics of organic light-emitting devices.

[0058] Chemical formula 1 contains at least one deuterium.

[0059] According to an exemplary embodiment of this specification, since the physicochemical properties of deuterium (e.g., bond length, etc.) differ from those of hydrogen, and the stretching amplitude of the CD bond is smaller than that of the CH bond, the van der Waals radius of deuterium is smaller than that of hydrogen, and generally, the CD bond is shorter and stronger than the CH bond. Therefore, if Formula 1 contains deuterium as a substituent, the energy of the ground state is reduced, and due to the shortening of the bond length between deuterium and carbon, the volume of the molecular hard core is reduced, and thus, the polarizability can be reduced, and the film volume can be increased due to the weakening of intermolecular interactions. Furthermore, these properties can provide the effect of reducing the crystallinity of the film (i.e., forming an amorphous state), and can generally be effective in improving the lifetime and operating characteristics of organic light-emitting devices, and the heat resistance can be improved compared to conventional organic light-emitting devices.

[0060] Examples of substituents described below are not limited to those in this specification.

[0061] In this instruction manual, Indicates a connection.

[0062] Throughout this specification, the term "combination thereof" used in Markush-type expressions means a mixture or combination of one or more of the constituent elements described in a Markush-type expression, and means including one or more of the constituent elements.

[0063] The term "substitution" refers to the replacement of a hydrogen atom bonded to a carbon atom in a compound by another substituent. There are no restrictions on the position of the substitution, as long as it is a position where a hydrogen atom can be substituted. When two or more substitutions are present, the two or more substituents can be the same or different.

[0064] The term "substituted or unsubstituted" in this specification means substituted with one or more of the following substituents: deuterium; halogen group; cyano; alkyl; cycloalkyl; alkoxy; alkenyl; haloalkyl; silyl; aryl; fused ring group of aromatic and aliphatic hydrocarbon rings; and heteroaryl, substituted with substituents connected to two or more of the above substituents, or without any substituents.

[0065] In this specification, the connection of two or more substituents means that the hydrogen of one substituent is attached to another substituent. For example, the connection of two substituents includes the formation of a structure through the connection of a phenyl and a naphthyl group. or Furthermore, the connection of three substituents not only includes the sequential connection of (substituent 1)-(substituent 2)-(substituent 3), but also includes the connection of (substituent 2) and (substituent 3) with (substituent 1). For example, phenyl, naphthyl, and isopropyl can be connected to form , or The above definition also applies to cases where four or more substituents are connected.

[0066] Examples of halogen groups in this specification include fluorine, chlorine, bromine, or iodine groups.

[0067] In this specification, alkyl groups may be linear or branched, and there is no particular limitation on the number of carbon atoms, but specifically from 1 to 30. Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, 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-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, etc., but are not limited to these.

[0068] In this specification, cycloalkyl groups may specifically have 3 to 30 carbon atoms, but are not particularly limited thereto. Specific examples include, but are 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, cyclooctyl, adamantyl, etc.

[0069] In this specification, alkoxy groups can be linear, branched, or cyclic. The number of carbon atoms in an alkoxy group is not particularly limited, but specifically ranges from 1 to 30. Specifically, it can be methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentoxy, neopentoxy, isopentoxy, n-hexyloxy, 3,3-dimethylbutoxy, 2-ethylbutoxy, n-octoxy, n-nonoxy, n-decoxy, benzyloxy, p-methylbenzyloxy, etc., but is not limited to these.

[0070] In this specification, the alkenyl group can be linear or branched, and the number of carbon atoms is not particularly limited, but specifically from 2 to 30. Specific examples include, but are not limited to, 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, Matrix, styrene, etc.

[0071] In this specification, haloalkyl means an alkyl group in which the hydrogen of the alkyl group is replaced by at least one halogen group.

[0072] In this specification, aryl is not particularly limited, but specifically refers to an aryl group having 6 to 30 carbon atoms, and the aryl group can be monocyclic or polycyclic.

[0073] When the aryl group is a monocyclic aryl group, there is no particular restriction on the number of carbon atoms, but it is specifically between 6 and 30. Specifically, monocyclic aryl groups can include, but are not limited to, phenyl, biphenyl, terphenyl, etc.

[0074] When the aryl group is a polycyclic aryl group, there is no particular restriction on the number of carbon atoms, but it is specifically between 10 and 30. Specifically, polycyclic aryl groups include, but are not limited to, naphthyl, anthraceneyl, phenanthrene, phenylene, pyrene, finadeninyl, etc. base, Benzyl, fluorene, etc.

[0075] In this specification, the fluorene group may be substituted and may be bonded to an adjacent group to form a ring.

[0076] Examples of fluorene include , , , , , , and And so on, but not limited to these.

[0077] In this specification, "adjacent" groups may mean a substituent that replaces an atom directly bonded to the atom substituted by the substituent, a substituent that is stereochemically closest to the substituent, or another substituent that replaces the atom substituted by the substituent. For example, two substituents that replace the atom in the ortho position of the benzene ring and two substituents that replace the atom in the same carbon aliphatic ring can be interpreted as "adjacent" groups.

[0078] In this specification, a heteroaryl group refers to a group comprising one or more non-carbon atoms or heteroatoms, and specifically, the heteroatoms may include one or more atoms selected from O, N, Se, S, etc. Specifically, a heteroaryl group may have 2 to 30 carbon atoms, but is not particularly limited thereto, and may be monocyclic or polycyclic. Examples of heteroaryl groups include thiophene, furanyl, pyrrole, imidazolyl, thiazolyl, etc. azole group, Diazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, triazolyl, acridineyl, pyridazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazenopyrazinyl, isoquinolinyl, indoleyl, carbazoleyl, benzo[] Azolyl, benzimidazolyl, benzothiazolyl, benzocarbazole, benzothiophene, dibenzothiophene, benzofuranyl, phenanthridine, phenanthrolinyl, iso Azolyl, thiadiazolyl, dibenzofuranyl, dibenzothiopyrrolyl, phen Thiol, phen Azinyl, phenothiazinyl, dihydroindocarbazolyl, spirofluorene Examples include, but are not limited to, ton-based, spirofluorene-thion-based, etc.

[0079] In this specification, silane can be alkylsilane, arylsilane, heteroarylsilane, etc. In alkylsilane, the alkyl group can be one of the alkyl groups exemplified above. In arylsilane, the aryl group can be one of the aryl groups exemplified above. And in heteroarylsilane, the heteroaryl group can be one of the heteroaryl groups exemplified above.

[0080] In this specification, the cycloalkyl group can be an aromatic cycloalkyl group, an aliphatic cycloalkyl group, or a fused cycloalkyl group of an aromatic and aliphatic cycloalkyl groups. The foregoing description of aryl groups applies to aromatic cycloalkyl groups, and the foregoing description of cycloalkyl groups applies to aliphatic cycloalkyl groups. Furthermore, fused cycloalkyl groups of aromatic and aliphatic cycloalkyl groups can have a structure in which the aforementioned aryl and cycloalkyl groups are fused together.

[0081] In this specification, the heterocyclic group can be an aromatic heterocyclic group, an aliphatic heterocyclic group, or a fused ring group of an aromatic heterocyclic group and an aliphatic heterocyclic group, and the foregoing description of heteroaryl groups can be applied to aromatic heterocyclic groups.

[0082] In this specification, arylene refers to a divalent aryl group having two bonding positions. The foregoing description of aryl groups can be applied, except that arylene is a divalent group.

[0083] In this specification, a heteroaryl group refers to a divalent heteroaryl group having two bonding positions. The foregoing description of heteroaryl groups can be applied, except that a heteroaryl group is a divalent group.

[0084] In this specification, a five-membered ring refers to a five-membered ring including the above-mentioned hydrocarbon cyclic group, heterocyclic group or their fused structure, the difference being that it is not a monovalent group.

[0085] In this specification, a six-membered ring refers to a six-membered ring including the above-mentioned aryl, heteroaryl, cycloalkyl or combinations thereof, the difference being that it is not a monovalent group.

[0086] In this specification, "or greater" means equal to or greater than (higher than or more than) the reference quantity, value, range, etc., "or less than" means equal to or less than (lower than or less than) the reference quantity, value, range, etc., "greater than" means greater than (higher than or more than) the reference quantity, value, range, etc., and "less than" means less than (lower than or less than) the reference quantity, value, range, etc.

[0087] Unless otherwise defined in this specification, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this disclosure pertains. While similar or equivalent methods and materials to those described in this specification may be used in practicing or testing embodiments of this disclosure, suitable methods and materials are described below. All publications, patent applications, patents, and other references mentioned in this specification are incorporated herein by reference in their entirety, and in the event of conflict, unless expressly stated otherwise, the descriptions (including definitions) in this specification shall prevail. Furthermore, materials, methods, and examples are illustrative only and are not intended to be limiting.

[0088] The compounds of chemical formula 1 are described in detail below.

[0089] According to an exemplary embodiment of this specification, in Formula 1, the substituted or unsubstituted aryl group, the substituted or unsubstituted heteroaryl group, the substituted or unsubstituted arylene group, the substituted or unsubstituted heteroarylene group, and the triplet energy level (T1) of Formula 2 are equal to or higher than [the specified value]. The triplet energy level.

[0090] According to an exemplary embodiment of this specification, in Formula 1 and Formula 2, the triplet energy levels (Ti) of substituted or unsubstituted aryl groups, substituted or unsubstituted heteroaryl groups, substituted or unsubstituted arylene groups, and substituted or unsubstituted heteroaryl groups are described. s 1) equal to or higher than The triplet energy level.

[0091] According to an exemplary embodiment of this specification, in Formula 1, substituted or unsubstituted aryl groups, substituted or unsubstituted heteroaryl groups, substituted or unsubstituted monocyclic or polycyclic arylenes, substituted or unsubstituted monocyclic or polycyclic heteroarylenes, and the triplet energy level (T) of Formula 2 are included. s 1) equal to or higher than The triplet energy level.

[0092] According to an exemplary embodiment of this specification, in Formula 1 and Formula 2, the triplet energy levels (Ti) of substituted or unsubstituted aryl groups, substituted or unsubstituted heteroaryl groups, substituted or unsubstituted monocyclic or polycyclic arylenes, and substituted or unsubstituted monocyclic or polycyclic heteroarylenes are described. s 1) equal to or higher than The triplet energy level.

[0093] According to an exemplary embodiment of this specification, in chemical formula 1, substituted or unsubstituted C 6-30 aryl, substituted or unsubstituted C 2-30 heteroaryl, substituted or unsubstituted C 6-30 Monocyclic or polycyclic arylene, substituted or unsubstituted C 2-30 Monocyclic or polycyclic heteroaryl groups, and the triplet energy level (T) of formula 2. s 1) equal to or higher than The triplet energy level.

[0094] According to an exemplary embodiment of this specification, in chemical formulas 1 and 2, substituted or unsubstituted C 6-30 aryl, substituted or unsubstituted C 2-30 heteroaryl, substituted or unsubstituted C 6-30 Monocyclic or polycyclic aryl groups, and substituted or unsubstituted C 2-30 triplet energy levels (Ti) of monocyclic or polycyclic heteroaryl groups s 1) equal to or higher than The triplet energy level.

[0095] That is, the triplet energy levels (Ti) of the substituents R1 to R12, L1, G1, G2, and G3 (excluding hydrogen and deuterium) in Formulas 1 and 2. s 1) equal to or higher than The triplet energy level.

[0096] According to an exemplary embodiment of this specification, chemical formula 1 The triplet energy level of the nucleus is 2.5 eV.

[0097] According to an exemplary embodiment of this specification, in Formula 1 and Formula 2, the triplet energy levels (Ti) of substituted or unsubstituted aryl groups, substituted or unsubstituted heteroaryl groups, substituted or unsubstituted arylene groups, and substituted or unsubstituted heteroaryl groups are described. s 1) 2.5 eV or higher.

[0098] That is, the triplet energy levels (Ti) of the substituents R1 to R12, L1, G1, G2, and G3 (excluding hydrogen and deuterium) in Formulas 1 and 2. s 1) 2.5 eV or higher.

[0099] According to an exemplary embodiment of this specification, in Formula 1 and Formula 2, the triplet energy levels (Ti) of substituted or unsubstituted aryl groups, substituted or unsubstituted heteroaryl groups, substituted or unsubstituted arylene groups, and substituted or unsubstituted heteroaryl groups are described. s 1) lower than The triplet energy level, and T s 1 and The energy difference between the triplet levels is greater than 0 eV and equal to or less than 0.2 eV. Alternatively, T s 1 and The energy difference between the triplet levels is greater than 0 eV and equal to or less than 0.1 eV.

[0100] According to an exemplary embodiment of this specification, in Formula 1, substituted or unsubstituted aryl groups, substituted or unsubstituted heteroaryl groups, substituted or unsubstituted monocyclic or polycyclic arylenes, substituted or unsubstituted monocyclic or polycyclic heteroarylenes, and the triplet energy level (T) of Formula 2 are included. s 1) lower than The triplet energy level, and T s 1 and The energy difference between the triplet levels is greater than 0 eV and equal to or less than 0.2 eV. Alternatively, T s 1 and The energy difference between the triplet levels is greater than 0 eV and equal to or less than 0.1 eV.

[0101] According to an exemplary embodiment of this specification, in Formula 1 and Formula 2, the triplet energy levels (Ti) of substituted or unsubstituted aryl groups, substituted or unsubstituted heteroaryl groups, substituted or unsubstituted monocyclic or polycyclic arylenes, and substituted or unsubstituted monocyclic or polycyclic heteroarylenes are described. s 1) lower than The triplet energy level, and T s 1 and The energy difference between the triplet levels is greater than 0 eV and equal to or less than 0.2 eV. Alternatively, Ts 1 and The energy difference between the triplet levels is greater than 0 eV and equal to or less than 0.1 eV.

[0102] According to an exemplary embodiment of this specification, in chemical formula 1, substituted or unsubstituted C 6-30 aryl, substituted or unsubstituted C 2-30 heteroaryl, substituted or unsubstituted C 6-30 Monocyclic or polycyclic arylene, substituted or unsubstituted C 2-30 Monocyclic or polycyclic heteroaryl groups, and the triplet energy level (T) of formula 2. s 1) lower than The triplet energy level, and T s 1 and The energy difference between the triplet levels is greater than 0 eV and equal to or less than 0.2 eV. Alternatively, T s 1 and The energy difference between the triplet levels is greater than 0 eV and equal to or less than 0.1 eV.

[0103] According to an exemplary embodiment of this specification, in chemical formulas 1 and 2, substituted or unsubstituted C 6-30 aryl, substituted or unsubstituted C 2-30 heteroaryl, substituted or unsubstituted C 6-30 Monocyclic or polycyclic aryl groups, and substituted or unsubstituted C 2-30 triplet energy levels (Ti) of monocyclic or polycyclic heteroaryl groups s 1) lower than The triplet energy level, and T s 1 and The energy difference between the triplet levels is greater than 0 eV and equal to or less than 0.2 eV. Alternatively, T s 1 and The energy difference between the triplet levels is greater than 0 eV and equal to or less than 0.1 eV.

[0104] That is, the triplet energy levels (Ti) of the substituents R1 to R12, L1, G1, G2, and G3 (excluding hydrogen and deuterium) in Formulas 1 and 2. s 1) lower than The triplet energy level, and T s 1 and The energy difference between the triplet levels is greater than 0 eV and equal to or less than 0.2 eV, or greater than 0 eV and equal to or less than 0.1 eV.

[0105] In other words, T s 1 and The triplet energy level is similar because it is similar to... The energy difference between the triplet levels is greater than 0 eV and equal to or less than 0.2 eV, and is related to T s 1 equals or is higher than The triplet energy level has the same effect.

[0106] According to an exemplary embodiment of this specification, in Formula 1 and Formula 2, the triplet energy levels (Ti) of substituted or unsubstituted aryl groups, substituted or unsubstituted heteroaryl groups, substituted or unsubstituted arylene groups, and substituted or unsubstituted heteroaryl groups are described. s 1) with The triplet energy levels are similar to or higher than those of the triplet energy levels.

[0107] Similarity can refer to T s 1 and The energy difference between the triplet levels is greater than 0 eV and equal to or less than 0.2 eV.

[0108] In this specification, energy level refers to the magnitude of energy. Therefore, even when an energy level is represented in the negative (-) direction from the vacuum energy level, the energy level is interpreted as referring to the absolute value of the corresponding energy level. For example, a low energy level or a deep energy level means an increase in absolute value from the vacuum energy level in the negative direction.

[0109] In this specification, the triplet energy can be measured using methods known in the art. Specifically, it can be measured at 77 K using a JASCO FP-8600 (a commercially available device). The measurement of the triplet energy is performed as follows. First, a sample is prepared by dissolving the compound to be measured in a suitable solvent and sealing it in a quartz glass tube. For this sample, the phosphorescence spectrum (ordinate: phosphorescence emission intensity, abscissa: wavelength) is measured at a low temperature (77 K), and a tangent is plotted at the beginning of the short-wavelength side of the phosphorescence spectrum. Then, the wavelength value λ at the intersection of the tangent and the abscissa is calculated by substituting into the following transformation formula. 边缘 (nm) Calculate the triplet energy.

[0110] Transformation: T1 (eV) = 1239.85 / λ 边缘

[0111] According to one exemplary embodiment of this specification, the triplet energy level (T1) of the compound of Formula 1 is 2.3 eV or higher. Furthermore, the triplet energy level (T1) of the compound of Formula 1 is 2.35 eV or higher, 2.37 eV or higher, 2.4 eV or higher, or 2.41 eV or higher, or 2.5 eV or higher.

[0112] According to one exemplary embodiment of this specification, m is 0.

[0113] According to one exemplary embodiment of this specification, m is 1.

[0114] According to one exemplary embodiment of this specification, chemical formula 2 is chemical formula 2-A or 2-B.

[0115] [Chemical Formula 2-A]

[0116]

[0117] [Chemical Formula 2-B]

[0118]

[0119] In chemical formulas 2-A and 2-B,

[0120] Y1, L1, l1, G1 to G3 and g1 to g3 are the same as those defined in Chemical Formula 2.

[0121] According to an exemplary embodiment of this specification, chemical formula 2 is any one of chemical formulas 2-1 to 2-7.

[0122] [Chemical Formula 2-1]

[0123]

[0124] [Chemical Formula 2-2]

[0125]

[0126] [Chemical Formula 2-3]

[0127]

[0128] [Chemical Formula 2-4]

[0129]

[0130] [Chemical Formula 2-5]

[0131]

[0132] [Chemical Formula 2-6]

[0133]

[0134] [Chemical Formula 2-7]

[0135]

[0136] In chemical formulas 2-1 to 2-7,

[0137] Y1, L1, l1, G1 to G3 and g1 to g3 are the same as those defined in Chemical Formula 2.

[0138] According to one exemplary embodiment of this specification, Y1 is O.

[0139] According to an exemplary embodiment of this specification, Y1 is S.

[0140] According to one exemplary embodiment of this specification, chemical formula 2 is any one of chemical formulas 2-8 to 2-14.

[0141] [Chemical Formula 2-8]

[0142]

[0143] [Chemical Formula 2-9]

[0144]

[0145] [Chemical Formula 2-10]

[0146]

[0147] [Chemical Formula 2-11]

[0148]

[0149] [Chemical Formula 2-12]

[0150]

[0151] [Chemical Formula 2-13]

[0152]

[0153] [Chemical Formula 2-14]

[0154]

[0155] In chemical formulas 2-8 to 2-14,

[0156] L1, l1, G1 to G3 and g1 to g3 are the same as those defined in Chemical Formula 2.

[0157] According to an exemplary embodiment of this specification, chemical formula 2 is any one of chemical formulas 2-15 to 2-21.

[0158] [Chemical Formula 2-15]

[0159]

[0160] [Chemical Formula 2-16]

[0161]

[0162] [Chemical Formula 2-17]

[0163]

[0164] [Chemical Formula 2-18]

[0165]

[0166] [Chemical Formula 2-19]

[0167]

[0168] [Chemical Formula 2-20]

[0169]

[0170] [Chemical Formula 2-21]

[0171]

[0172] In chemical formulas 2-15 to 2-21,

[0173] L1, l1, G1 to G3 and g1 to g3 are the same as those defined in Chemical Formula 2.

[0174] According to an exemplary embodiment of this specification, at least one of R1 to R4, R6 to R10 and R12 is chemical formula 2.

[0175] According to an exemplary embodiment of this specification, any one of R1 to R4, R6 to R10 and R12 is chemical formula 2.

[0176] According to an exemplary embodiment of this specification, any two of R1 to R4, R6 to R10 and R12 are chemical formula 2.

[0177] According to an exemplary embodiment of this specification, any three of R1 to R4, R6 to R10 and R12 are chemical formula 2.

[0178] According to one exemplary embodiment of this specification, R1 is chemical formula 2.

[0179] According to one exemplary embodiment of this specification, R2 is chemical formula 2.

[0180] According to one exemplary embodiment of this specification, R3 is chemical formula 2.

[0181] According to one exemplary embodiment of this specification, R6 is chemical formula 2.

[0182] According to one exemplary embodiment of this specification, R12 is chemical formula 2.

[0183] According to one exemplary embodiment of this specification, R1 and R2 may be the same or different, and are independently of chemical formula 2.

[0184] According to one exemplary embodiment of this specification, R1 and R3 may be the same or different, and are independently of chemical formula 2.

[0185] According to one exemplary embodiment of this specification, R1 and R6 may be the same or different, and are independently of chemical formula 2.

[0186] According to one exemplary embodiment of this specification, R1 and R12 may be the same or different, and are independently of chemical formula 2.

[0187] According to one exemplary embodiment of this specification, R2 and R3 may be the same or different, and are independently of chemical formula 2.

[0188] According to one exemplary embodiment of this specification, R2 and R6 may be the same or different, and are independently of chemical formula 2.

[0189] According to one exemplary embodiment of this specification, R2 and R12 may be the same or different, and are independently of chemical formula 2.

[0190] According to one exemplary embodiment of this specification, R3 and R6 may be the same or different, and are independently of chemical formula 2.

[0191] According to one exemplary embodiment of this specification, R3 and R12 may be the same or different, and are independently of chemical formula 2.

[0192] According to one exemplary embodiment of this specification, R6 and R12 may be the same or different, and are independently of chemical formula 2.

[0193] According to one exemplary embodiment of this specification, R1 to R3 may be the same or different, and are independently of chemical formula 2.

[0194] According to one exemplary embodiment of this specification, R1, R2, and R6 may be the same or different, and are independently of chemical formula 2.

[0195] According to one exemplary embodiment of this specification, R1, R3, and R6 may be the same or different, and are independently of chemical formula 2.

[0196] According to one exemplary embodiment of this specification, R2, R3, and R6 may be the same or different, and are independently of chemical formula 2.

[0197] According to one exemplary embodiment of this specification, R1 to R3 and R6 may be the same or different, and are independently of chemical formula 2.

[0198] According to an exemplary embodiment of this specification, chemical formula 1 is any one of chemical formulas 1-1 to 1-6.

[0199] [Chemical Formula 1-1]

[0200]

[0201] [Chemical Formula 1-2]

[0202]

[0203] [Chemical Formulas 1-3]

[0204]

[0205] [Chemical Formulas 1-4]

[0206]

[0207] [Chemical Formulas 1-5]

[0208]

[0209] [Chemical Formulas 1-6]

[0210]

[0211] In chemical formulas 1-1 to 1-6,

[0212] Y1, L1, l1, G1 to G3 and g1 to g3 are the same as those defined in chemical formula 2.

[0213] R1 to R12 may be the same or different, and are independently hydrogen; deuterium; substituted or unsubstituted aryl; or substituted or unsubstituted heteroaryl.

[0214] Y11 is either O or S.

[0215] L11 is a direct bond; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group.

[0216] l11 is either 1 or 2, and if l11 is 2, then L11 is either the same or different.

[0217] G11 to G13 may be the same or different, and are independently hydrogen; deuterium; deuterated or unsubstituted phenyl; deuterated or unsubstituted biphenyl; deuterated or unsubstituted naphthyl; deuterated or unsubstituted phenanthryl; or deuterated or unsubstituted C 5-20 Mixed aromatics,

[0218] g11 to g13 are each an integer from 1 to 4.

[0219] If g11 is 2 or greater, then two or more G11 values ​​are the same or different.

[0220] If g12 is 2 or greater, then two or more G12 values ​​are the same or different.

[0221] If g13 is 2 or greater, then two or more G13s are the same or different.

[0222] m' is 0 or 1.

[0223] If m' is 0, then g12 is an integer from 1 to 4, and g11 + g12 ≤ 7, and

[0224] If m' is 1, then g12 is 1 or 2, and g11+g12+g13≤9.

[0225] According to one exemplary embodiment of this specification, the deuterium substitution rate of chemical formula 1 is 1% or higher.

[0226] According to one exemplary embodiment of this specification, the deuterium substitution rate of chemical formula 1 is 2% or higher.

[0227] According to one exemplary embodiment of this specification, the deuterium substitution rate of chemical formula 1 is 10% or higher.

[0228] According to one exemplary embodiment of this specification, the deuterium substitution rate of chemical formula 1 is 15% or higher.

[0229] According to one exemplary embodiment of this specification, the deuterium substitution rate of chemical formula 1 is from 1% to 100%.

[0230] According to one exemplary embodiment of this specification, the deuterium substitution rate of chemical formula 1 is from 2% to 100%.

[0231] According to one exemplary embodiment of this specification, the deuterium substitution rate of chemical formula 1 is 10% to 100%.

[0232] According to one exemplary embodiment of this specification, the deuterium substitution rate of chemical formula 1 is 15% to 100%.

[0233] According to one exemplary embodiment of this specification, the deuterium substitution rate of chemical formula 1 is from 1% to 99.9%.

[0234] According to one exemplary embodiment of this specification, the deuterium substitution rate of chemical formula 1 is from 2% to 99.9%.

[0235] According to one exemplary embodiment of this specification, the deuterium substitution rate of chemical formula 1 is from 10% to 99.9%.

[0236] According to one exemplary embodiment of this specification, the deuterium substitution rate of chemical formula 1 is from 15% to 99.9%.

[0237] In this specification, "containing deuterium", "deuterated" or "deuterated" means that hydrogen at a substituted position in the compound is replaced by deuterium.

[0238] In this specification, "fully deuterated" means a compound or group in which all hydrogen atoms in the molecule are replaced by deuterium, and has the same meaning as "100% deuterated".

[0239] In this specification, "X% deuterated", "degree of deuteration X%", or "deuteration rate X%" means that X% of the hydrogens at the substituted positions in the structure are replaced by deuterium. For example, when the structure is dibenzofuran, "25% deuterated" dibenzofuran, "degree of deuteration of 25%" dibenzofuran, or "deuteration rate of 25%" dibenzofuran can mean that 2 out of the 8 hydrogens at the substituted positions in dibenzofuran are replaced by deuterium, or it can mean that all 8 hydrogens at the substituted positions are replaced by 25% deuterium, or that 4 out of the 8 hydrogens at the substituted positions are replaced by 50% deuterium.

[0240] In this specification, the substituted deuterium has a deuterium substitution rate of 1% or higher and 99.9% or lower.

[0241] In this specification, "degree of deuteration" or "deuteration substitution rate" can be determined by known methods such as nuclear magnetic resonance spectroscopy (NMR spectroscopy). 1 It can be determined by methods such as ¹H NMR, thin-layer chromatography / mass spectrometry (TLC / MS), and gas chromatography / mass spectrometry (GC / MS).

[0242] Specifically, when measured by nuclear magnetic resonance spectroscopy (NMR spectroscopy) 1 When analyzing "degree of deuteration" or "rate of deuteration" using ¹H NMR, the degree of deuteration or rate of deuteration can be determined by adding dimethylformamide (DMF) as an internal standard. 1 Calculation of the integrated peak area on the H NMR spectrum.

[0243] Furthermore, when analyzing "degree of deuteration" or "deuteration substitution rate" by thin-layer chromatography / mass spectrometry (TLC / MS), the substitution rate can be calculated based on the maximum (median) value of the molecular weight distribution at the reaction endpoint. For example, when analyzing the degree of deuteration of compound A, if the molecular weight of the starting material is 506 and... Figure 5 The maximum molecular weight (median) of compound A in the MS spectrum is 527. Therefore, 21 of the 26 hydrogens at the substituted positions of the starting material are replaced by deuterium, and thus it can be calculated that about 81% of the hydrogens are deuterated.

[0244]

[0245] [Starting Material] [Compound A]

[0246] In this specification, D represents deuterium.

[0247] According to an exemplary embodiment of this specification, at least one of R1 to R12 is of chemical formula 2, and the remaining R1 to R12 that are not of chemical formula 2 are the same or different, and are independently hydrogen; deuterium; or substituted or unsubstituted aryl groups.

[0248] According to an exemplary embodiment of this specification, at least one of R1 to R12 is of chemical formula 2, and the remaining R1 to R12 that are not of chemical formula 2 are the same or different, and are independently hydrogen; deuterium; or substituted or unsubstituted C. 6-30 Monocyclic or polycyclic aryl groups.

[0249] According to an exemplary embodiment of this specification, at least one of R1 to R12 is of chemical formula 2, and the remaining R1 to R12 that are not of chemical formula 2 are the same or different, and are independently hydrogen; deuterium; or deuterated, C 6-30 Monocyclic or polycyclic aryl groups or combinations thereof substituted or unsubstituted C 6-30 Monocyclic or polycyclic aryl groups.

[0250] According to an exemplary embodiment of this specification, at least one of R1 to R12 is of chemical formula 2, and the remaining R1 to R12 that are not of chemical formula 2 are the same or different, and are independently hydrogen; deuterium; a phenyl substituted with or unsubstituted with deuterium, phenyl, biphenyl, naphthyl or a combination thereof; a biphenyl substituted with or unsubstituted with deuterium, phenyl or a combination thereof; a terphenyl substituted with or unsubstituted with deuterium; a naphthyl substituted with or unsubstituted with deuterium, phenyl, naphthyl or a combination thereof; or a phenanthryl substituted with or unsubstituted with deuterium.

[0251] According to one exemplary embodiment of this specification, L1 is a direct bond; or a substituted or unsubstituted aryl group.

[0252] According to an exemplary embodiment of this specification, L1 is a direct bond; a substituted or unsubstituted monocyclic or polycyclic aryl group; or a substituted or unsubstituted monocyclic or polycyclic heteroaryl group.

[0253] According to an exemplary embodiment of this specification, L1 is a direct bond; a substituted or unsubstituted monocyclic aryl group; or a substituted or unsubstituted polycyclic heteroaryl group.

[0254] According to one exemplary embodiment of this specification, L1 is a direct key; or a substituted or unsubstituted C key. 6-30 Monocyclic or polycyclic aryl groups.

[0255] According to one exemplary embodiment of this specification, L1 is a direct key; C is substituted or unsubstituted. 6-30 Monocyclic or polycyclic arylene groups; or substituted or unsubstituted C 2-30 Monocyclic or polycyclic heteroaryl groups.

[0256] According to one exemplary embodiment of this specification, L1 is a direct key; C is substituted or unsubstituted. 6-30 Monocyclic aryl; or substituted or unsubstituted C 2-30 Polycyclic heteroaryl groups.

[0257] According to an exemplary embodiment of this specification, L1 is a direct bond; a substituted or unsubstituted monocyclic or polycyclic aryl group; or a substituted or unsubstituted monocyclic or polycyclic heteroaryl group containing O or S.

[0258] According to an exemplary embodiment of this specification, L1 is a direct bond; a substituted or unsubstituted monocyclic aryl group; or a substituted or unsubstituted polycyclic heteroaryl group containing O or S.

[0259] According to one exemplary embodiment of this specification, L1 is a direct key; C is substituted or unsubstituted. 6-30 Monocyclic or polycyclic arylene groups; or substituted or unsubstituted C groups containing O or S. 2-30 Monocyclic or polycyclic heteroaryl groups.

[0260] According to one exemplary embodiment of this specification, L1 is a direct key; C is substituted or unsubstituted. 6-30 Monocyclic aryl; or substituted or unsubstituted C containing O or S. 2-30 Polycyclic heteroaryl groups.

[0261] According to one exemplary embodiment of this specification, L1 is a direct key; or via deuterium, C 6-30 Monocyclic or polycyclic aryl groups or combinations thereof substituted or unsubstituted C 6-30 Monocyclic or polycyclic aryl groups.

[0262] According to one exemplary embodiment of this specification, L1 is a direct key; or via deuterium, C 6-30 Monocyclic or polycyclic aryl groups or combinations thereof substituted or unsubstituted C 6-30 Monocyclic aryl.

[0263] According to an exemplary embodiment of this specification, L1 is a direct bond; a phenylene substituted with or unsubstituted with deuterium, biphenyl, naphthyl or a combination thereof; a biphenylene substituted with or unsubstituted with deuterium, phenyl or a combination thereof; or a terphenylene substituted with or unsubstituted with deuterium.

[0264] According to one exemplary embodiment of this specification, G1 to G3 may be the same or different, and are independently hydrogen; deuterium; a deuterated or unsubstituted phenyl; a deuterated or unsubstituted biphenyl; a deuterated or unsubstituted naphthyl; a deuterated or unsubstituted phenanthryl; or a deuterated or unsubstituted C 5-20 Mixed aromatic compounds.

[0265] According to one exemplary embodiment of this specification, G1 to G3 may be the same or different, and are independently hydrogen; deuterium; a deuterated or unsubstituted phenyl; a deuterated or unsubstituted biphenyl; a deuterated or unsubstituted naphthyl; a deuterated or unsubstituted phenanthryl; or a deuterated or unsubstituted C 5-20 Monocyclic to pentacyclic heteroaryl groups.

[0266] According to an exemplary embodiment of this specification, G1 to G3 may be the same or different, and are independently hydrogen; deuterium; a deuterated or unsubstituted phenyl; a deuterated or unsubstituted biphenyl; a deuterated or unsubstituted naphthyl; a deuterated or unsubstituted phenanthryl; a deuterated or unsubstituted benzofuranyl; a deuterated or unsubstituted dibenzofuranyl; a deuterated or unsubstituted benzothiophenyl; or a deuterated or unsubstituted dibenzothiophenyl.

[0267] According to an exemplary embodiment of this specification, chemical formula 1 is one of the following compounds.

[0268]

[0269]

[0270]

[0271]

[0272]

[0273]

[0274]

[0275]

[0276]

[0277]

[0278]

[0279]

[0280]

[0281]

[0282]

[0283]

[0284] According to an exemplary embodiment of this specification, compounds of Formula 1 can be prepared into a core structure according to the methods described in the preparation examples below. Other substituents can be combined by methods known in the art, and the type, position, or number of substituents can be varied according to techniques known in the art.

[0285] In this specification, compounds with various band gaps can be synthesized by introducing various substituents into the core structure of the compound represented by Formula 1. Furthermore, in this specification, the HOMO and LUMO energy levels of the compound can be controlled by introducing various substituents into the core structure.

[0286] In addition, this specification provides organic light-emitting devices containing the aforementioned compounds.

[0287] In this specification, when a component is described as being "on" another component, this includes not only the case where the component is in contact with the other component, but also the case where there is another component between the two components.

[0288] In this disclosure, when a part is referred to as "including" a component, it means, unless otherwise stated, that other components may also be included.

[0289] In this specification, the term "layer" is used interchangeably with "film," and the term "layer" is primarily used in this art, referring to a coating that covers a target area. There is no limitation on the size of a "layer," and the dimensions of individual "layers" can be the same or different. In one exemplary embodiment, the size of a "layer" can be the same as the size of the entire device, can correspond to the size of a specific functional region, or can be as small as a single subpixel.

[0290] In this specification, the meaning of "a layer B contains a specific material A" includes both of the following: i) a layer B contains one or more materials A; and ii) a layer B consists of one or more layers, and one or more of the multiple layers B contain materials A.

[0291] In this specification, the inclusion of a specific material A in a C layer or a D layer means: i) at least one of one or more C layers contains material A; ii) at least one of one or more D layers contains material A; or iii) one or more C layers and one or more D layers contain material A.

[0292] The organic light-emitting device according to this specification is an organic light-emitting device comprising: an anode; a cathode; and one or more organic layers disposed between the anode and the cathode, wherein at least one of the organic layers contains the compound represented by chemical formula 1 described above.

[0293] The organic light-emitting device described in this specification can be prepared using conventional methods and materials for preparing organic light-emitting devices, except that the organic layer is formed using a compound of the above-described chemical formula 1.

[0294] During the fabrication of organic light-emitting devices, the compound can be formed into an organic layer using solution coating and vacuum deposition methods. Here, solution coating methods refer to, but are not limited to, spin coating, dip coating, inkjet printing, screen printing, spraying, and roll coating.

[0295] The organic layers of the organic light-emitting device described in this specification can be formed as a single-layer structure, but they can also be formed as a multilayer structure in which two or more organic layers are stacked. For example, the organic light-emitting device of this disclosure can have a structure including at least one of the following layers as organic layers: a hole transport layer, a hole injection layer, an electron blocking (hole control) layer, a hole transport and injection layer, a light-emitting layer, an electron transport layer, an electron injection layer, a hole blocking (electron control) layer, and an electron transport and injection layer. However, the structure of the organic light-emitting device of this specification is not limited to this, and may include fewer or more organic layers.

[0296] At this point, the light-emitting layer may contain the aforementioned compound as the main body of the light-emitting layer, and may also contain other main bodies and dopants. The other main bodies may be contained together with the aforementioned compound in the organic layer, or they may be contained in another adjacent organic layer.

[0297] In the organic light-emitting device of this specification, the light-emitting layer may comprise a host and a dopant, and the total host and dopant may be contained in a weight ratio of 99:1 to 1:99, specifically 99:1 to 70:30, and more specifically 99:1 to 85:15.

[0298] According to an exemplary embodiment of this specification, the light-emitting layer is a blue light-emitting layer with a maximum emission wavelength of 440 nm to 480 nm.

[0299] The organic light-emitting device described in this specification may also include one or more organic layers from the following: hole transport layer, hole injection layer, electron blocking (hole control) layer, electron injection and transport layer, electron transport layer, electron injection layer, hole blocking (electron control) layer, and hole injection and transport layer.

[0300] In one exemplary embodiment of this specification, the organic light-emitting device includes an anode; a cathode; and two or more organic layers disposed between the anode and the cathode, wherein at least one of the two or more organic layers contains a compound represented by chemical formula 1.

[0301] In one exemplary embodiment of this specification, the organic light-emitting device can be an organic light-emitting device (normal type) having a structure in which an anode, one or more organic layers, and a cathode are sequentially stacked on a substrate.

[0302] In one exemplary embodiment of this specification, the organic light-emitting device may be an organic light-emitting device (inverted type) in which the cathode, one or more organic layers, and the anode are sequentially stacked on a substrate.

[0303] The structure of the organic light-emitting device described in this specification can have the following characteristics: Figures 1 to 4 The structures shown are examples of, but not limited to, those described.

[0304] Figure 1 The structure of an organic light-emitting device in which a substrate 1, an anode 2, a light-emitting layer 6, and a cathode 10 are sequentially stacked is shown. In this structure, the compound may be contained in the light-emitting layer 6.

[0305] Figure 2 The diagram illustrates the structure of an organic light-emitting device in which a substrate 1, an anode 2, a hole injection layer 3, a hole transport layer 4, an electron blocking (hole control) layer 5, a light-emitting layer 6, a hole blocking (electron control) layer 7, an electron transport layer 8, an electron injection layer 9, and a cathode 10 are sequentially stacked. In this structure, the compound may be contained within the light-emitting layer 6.

[0306] Figure 3 The diagram illustrates the structure of an organic light-emitting device in which a substrate 1, an anode 2, a hole injection and transport layer 34, a light-emitting layer 6, an electron transport layer 8, an electron injection layer 9, and a cathode 10 are sequentially stacked. In this structure, the compound may be contained within the light-emitting layer 6.

[0307] Figure 4 The diagram illustrates the structure of an organic light-emitting device in which a substrate 1, an anode 2, a hole injection and transport layer 34, a first light-emitting layer 6-1, a second light-emitting layer 6-2, an electron transport layer 8, an electron injection layer 9, and a cathode 10 are sequentially stacked. In this structure, the compound may be contained in the first light-emitting layer 6-1.

[0308] In one exemplary embodiment of this specification, the electron transport layer comprises at least one layer. When the electron transport layer comprises two layers, it includes a first electron transport layer and a second electron transport layer, wherein the first electron transport layer is disposed in contact with the second light-emitting layer, and the second electron transport layer is disposed on the first electron transport layer. That is, the first electron transport layer may be disposed between the second light-emitting layer and the second electron transport layer.

[0309] In one exemplary embodiment of this specification, the electron blocking (hole control) layer and the light-emitting layer may be disposed adjacent to each other. For example, the electron blocking (hole control) layer and the light-emitting layer may be disposed in physical contact.

[0310] In one exemplary embodiment of this specification, the hole transport layer and the electron blocking (hole control) layer may be disposed adjacent to each other. For example, the hole transport layer and the electron blocking (hole control) layer may be disposed in physical contact.

[0311] The organic light-emitting devices described herein can be prepared using materials and methods known in the art, except that at least one of the organic layers contains the compound described herein, namely the compound of formula 1.

[0312] When an organic light-emitting device comprises multiple organic layers, the organic layers can be formed from the same material or different materials.

[0313] For example, the organic light-emitting device according to this specification can be fabricated by depositing a metal or conductive metal oxide or alloy thereof on a substrate using a PVD (physical vapor deposition) method such as sputtering or electron beam evaporation to form an anode; forming an organic layer on the anode comprising a hole injection layer, a hole transport layer, a light-emitting layer, an electron blocking (hole control) layer, an electron transport layer, and an electron injection layer; and then depositing a material that can be used as a cathode on the organic layer. Alternatively, the organic light-emitting device can also be fabricated by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate.

[0314] Furthermore, when the organic layer of an organic light-emitting device contains two or more compounds, it can be deposited using a co-deposition method or a premixing method.

[0315] The organic layer may also include at least one layer from the following: a hole transport layer, a hole injection layer, an electron blocking (hole control) layer, an electron transport and injection layer, an electron transport layer, an electron injection layer, a hole blocking (electron control) layer, and a hole injection and transport layer.

[0316] Organic layers can have multilayer structures including, but are not limited to, hole injection layers, hole transport layers, hole injection and transport layers, electron blocking (hole control) layers, light-emitting layers, and electron transport layers, electron injection layers, and electron injection and transport layers. They can also have single-layer structures. Furthermore, organic layers can be prepared using various polymer materials via solvent-based methods rather than deposition methods, such as spin coating, dip coating, blade coating, screen printing, inkjet printing, and thermal transfer, to achieve a smaller number of layers.

[0317] The anode is the electrode into which holes are injected. A high work function is preferred as the anode material, allowing for smooth hole injection, typically into an organic layer. Specific examples of anode materials that can be used in this disclosure include, but are not limited to, metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline; and so on.

[0318] The cathode is the electrode into which electrons are injected. Specifically, the cathode material can be a material with a low work function, which facilitates electron injection, typically into an organic layer. Specific examples of cathode materials include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; multilayer materials such as LiF / Al or LiO2 / Al; and so on.

[0319] The hole injection layer serves to smoothly inject holes from the anode into the light-emitting layer. The hole injection material is one that can effectively inject holes from the anode at low voltages, and preferably, the HOMO (highest occupied molecular orbital) of the hole injection material lies between the work function of the anode and the HOMO of the surrounding organic layer. Specific examples of hole injection materials include, but are not limited to, metalloporphyrins, oligothiophenes, arylamine-based compounds, hexanitrile hexaazabenzophenanthrene-based compounds, quinacridone-based compounds, and others. Compounds, including arylamine-based compounds, benzyl nitrile-based compounds, anthraquinones, polyaniline-based and polythiophene-based conductive polymers, etc. Specifically, arylamine-based compounds and benzyl nitrile-based compounds can be used in the hole injection layer.

[0320] In the organic light-emitting devices described in this specification, compounds based on arylamines substituted with carbazole groups and compounds based on benzyl nitrile groups substituted with halogen groups may be used in the hole injection layer, but are not limited thereto.

[0321] According to one exemplary embodiment of this specification, the hole injection layer comprises, but is not limited to, a compound represented by the chemical formula HI-1.

[0322] [Chemical formula HI-1]

[0323]

[0324] In the chemical formula HI-1,

[0325] R315 to R317 may be the same or different, and are independently selected from any of the following: hydrogen; deuterium; substituted or unsubstituted alkyl; substituted or unsubstituted aryl; substituted or unsubstituted heteroaryl; and combinations thereof, or combined with adjacent groups to form substituted or unsubstituted rings.

[0326] r315 is an integer from 1 to 5, and if r315 is 2 or greater, then two or more r315 are the same or different.

[0327] r316 is an integer from 1 to 5. If r316 is 2 or greater, then two or more R316 are the same or different.

[0328] According to an exemplary embodiment of this specification, R317 is selected from any of the following: substituted or unsubstituted aryl groups; substituted or unsubstituted heteroaryl groups; and combinations thereof.

[0329] According to an exemplary embodiment of this specification, R317 is selected from any of the following: carbazolyl; phenyl; biphenyl; triphenylene; and combinations thereof.

[0330] According to one exemplary embodiment of this specification, R315 and R316 may be the same or different, independently being substituted or unsubstituted aryl groups, or bonded to adjacent groups to form an aryl or alkyl-substituted aromatic ring.

[0331] According to one exemplary embodiment of this specification, R315 and R316 may be the same or different, independently phenyl or biphenyl, or bonded to adjacent groups to form indene substituted with phenyl or methyl groups.

[0332] According to an exemplary embodiment of this specification, the chemical formula HI-1 is represented by one of the following compounds.

[0333]

[0334] According to one exemplary embodiment of this specification, the hole injection layer comprises a compound represented by the chemical formula HI-2, but is not limited thereto.

[0335] [Chemical formula HI-2]

[0336]

[0337] In the chemical formula HI-2,

[0338] R411 to R413 may be the same or different, and are independently halogen groups, and

[0339] r411 to r413 are each 4.

[0340] According to an exemplary embodiment of this specification, R411 to R413 are each F.

[0341] According to one exemplary embodiment of this specification, the chemical formula HI-2 is represented by the following compound.

[0342]

[0343] According to an exemplary embodiment of this specification, the hole injection layer comprises chemical formula HI-1 and chemical formula HI-2.

[0344] According to an exemplary embodiment of this specification, the hole injection layer comprises chemical formulas HI-1 and HI-2 in a weight ratio of 1:99 to 99:1. Specifically, they are included in a weight ratio of 10:90 to 90:10.

[0345] Hole transport layers can facilitate hole transport. Suitable hole transport materials are those with high hole mobility, capable of transporting holes from the anode or hole injection layer and transferring them to the light-emitting layer. Specific examples of hole transport materials include, but are not limited to, arylamine-based compounds, carbazole compounds, conductive polymers, and block copolymers containing both conjugated and non-conjugated portions.

[0346] In the organic light-emitting devices described in this specification, carbazole-based compounds substituted with aryl amine groups can be used as the hole transport layer, but are not limited thereto.

[0347] According to one exemplary embodiment of this specification, the hole transport layer comprises, but is not limited to, a compound represented by the chemical formula HI-1.

[0348] An electron blocking (hole control) layer can be disposed between the hole transport layer and the light-emitting layer. The electron blocking (hole control) layer prevents electrons from flowing from the light-emitting layer into the anode and controls the flow of holes into the light-emitting layer to control the overall device performance. As an electron blocking material (hole control material), a compound with the ability to prevent electrons from flowing from the light-emitting layer into the anode and control the flow of holes injected into the light-emitting layer or light-emitting material is preferred. In one exemplary embodiment, an arylamine-based organic material can be used in the electron blocking (hole control) layer, but is not limited thereto.

[0349] In the organic light-emitting devices described in this specification, the electron blocking (hole control) layer may comprise an amine compound containing a carbazole group. For example, the compound may be a compound in which the carbazole group and the amine group are linked by an ortho-, meta-, or para-biphenyl group.

[0350] According to one exemplary embodiment of this specification, the electron blocking (hole control) layer comprises, but is not limited to, a compound of the chemical formula EG-1.

[0351] [Chemical formula EB-1]

[0352]

[0353] In chemical formula EB-1,

[0354] R501 to R504 may be the same or different, and are independently hydrogen; deuterium; substituted or unsubstituted aryl; or substituted or unsubstituted heterocyclic groups.

[0355] L101 is a direct bond; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group.

[0356] Ar101 and Ar102 may be the same or different, independently being substituted or unsubstituted aryl groups; or substituted or unsubstituted heteroaryl groups, and

[0357] l101 is an integer from 1 to 3, and if l101 is 2 or greater, then two or more L101 are the same or different.

[0358] R501 is an integer from 1 to 5, and if r501 is 2 or greater, then two or more R501 values ​​are the same or different.

[0359] R504 is an integer from 1 to 5, and if r504 is 2 or greater, then two or more R504 values ​​are the same or different.

[0360] R502 is an integer from 1 to 3, and if r502 is 2 or greater, then two or more R502 values ​​are the same or different.

[0361] R503 is an integer from 1 to 4, and if r503 is 2 or greater, then two or more R503s are the same or different.

[0362] According to one exemplary embodiment of this specification, R501 to R504 may be the same or different, and are independently hydrogen; or deuterium.

[0363] According to one exemplary embodiment of this specification, R501 to R504 are hydrogen.

[0364] According to one exemplary embodiment of this specification, L101 is a direct key; or C 6-30 Monocyclic or polycyclic aryl groups.

[0365] According to an exemplary embodiment of this specification, L101 is a direct bond; phenylene; or naphthylene.

[0366] According to one exemplary embodiment of this specification, L101 is a direct key.

[0367] According to one exemplary embodiment of this specification, Ar101 and Ar102 may be the same or different, and are independently C 6-30 Monocyclic or polycyclic aryl groups.

[0368] According to one exemplary embodiment of this specification, Ar101 and Ar102 may be the same or different, and are independently phenyl; biphenyl; or naphthyl.

[0369] According to an exemplary embodiment of this specification, EB-1 is represented by one of the following compounds:

[0370]

[0371] The luminescent layer can emit red, green, or blue light and can be made of phosphorescent or fluorescent materials. The aforementioned luminescent materials are those capable of emitting light in the visible light range by transferring and combining holes and electrons from the hole transport layer and electron transport layer, respectively. Specifically, materials with good quantum efficiency for fluorescence or phosphorescence can be used. Specific examples include, but are not limited to, 8-hydroxyquinoline aluminum complexes (Alq3); carbazole compounds; dipolystyrene compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; and benzo[…]. Zyrazoles, benzothiazole-based and benzimidazole-based compounds; polymers based on poly(p-phenylenevinylene) (PPV); spirocyclic compounds; polyfluorene; red fluorene; etc.

[0372] The main materials of the luminescent layer include fused aromatic ring derivatives and heterocyclic compounds. Specifically, fused aromatic ring derivatives include anthracene-based derivatives, pyrene derivatives, naphthalene derivatives, pentane derivatives, phenanthrene compounds, fluoranthene compounds, etc., and heterocyclic compounds include carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, pyrimidine derivatives, etc., but are not limited to these.

[0373] In the organic light-emitting device described in this specification, the main body may be a compound of the above-mentioned chemical formula 1 or an anthracene-based derivative, but is not limited thereto.

[0374] In the organic light-emitting device described in this specification, the host may contain a compound of chemical formula 1 as a first host, and may also contain a second host.

[0375] In the organic light-emitting device described in this specification, the second host can be a compound with the chemical formula H.

[0376] [Chemical formula H]

[0377]

[0378] In the chemical formula H,

[0379] L20 and L21 may be the same or different, and are independently direct bonds; substituted or unsubstituted aryl groups; or substituted or unsubstituted divalent heterocyclic groups.

[0380] Ar20 and Ar21 may be the same or different, and are independently hydrogen; deuterium; substituted or unsubstituted aryl; or substituted or unsubstituted heterocyclic groups.

[0381] R301 is hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, and

[0382] r301 is an integer from 1 to 8, and if r301 is 2 or greater, then two or more R301 are the same or different.

[0383] In one exemplary embodiment of this specification, the first body comprises at least one compound of formula 1.

[0384] In one exemplary embodiment of this specification, the first body comprises two or more compounds of chemical formula 1, and the two or more compounds may be the same or different.

[0385] In one exemplary embodiment of this specification, the first body comprises a compound of formula 1, and may also comprise at least one compound based on formula 1. Compounds.

[0386] In one exemplary embodiment of this specification, the first body comprises a compound of formula 1, and may also comprise at least one compound based on formula 1. Compounds, and at least one non-based Compounds. Not based on The compounds may include, but are not limited to, compounds with higher triplet energy than the chemical formula H.

[0387] based on compounds and non-based The compounds can be existing compounds, but are not limited to them.

[0388] In one exemplary embodiment of this specification, the second body comprises a compound of chemical formula H, and may also comprise at least one anthracene-based compound different from chemical formula H.

[0389] In one exemplary embodiment of this specification, the second body comprises a compound of chemical formula H, and may also comprise an anthracene-based compound different from chemical formula H.

[0390] In one exemplary embodiment of this specification, the second body may be two or more compounds of the chemical formula H, wherein the two or more compounds are different from each other.

[0391] Anthracene-based compounds can be existing compounds, but are not limited to them.

[0392] In one exemplary embodiment of this specification, L20 and L21 may be the same or different, and are independently direct keys; C 6-30 Monocyclic or polycyclic arylene; or C 2-30 Monocyclic or polycyclic divalent heterocyclic groups.

[0393] In one exemplary embodiment of this specification, L20 and L21 may be the same or different, and are independently direct bonds; deuterated or unsubstituted phenylene; deuterated or unsubstituted biphenylene; deuterated or unsubstituted naphthylene; divalent dibenzofuranyl; or divalent dibenzothiopheneyl.

[0394] In one exemplary embodiment of this specification, Ar20 and Ar21 may be the same or different, and are independently substituted or unsubstituted C. 6-30 Monocyclic or polycyclic aryl groups; or substituted or unsubstituted C 2-30 Monocyclic or polycyclic heterocyclic groups.

[0395] In one exemplary embodiment of this specification, Ar20 and Ar21 may be the same or different, and are independently substituted or unsubstituted C. 6-20 Monocyclic to tetracyclic aryl; or substituted or unsubstituted C 6-20 Monocyclic to tetracyclic heterocyclic groups.

[0396] In one exemplary embodiment of this specification, Ar20 and Ar21 may be the same or different, and are independently deuterated or C. 6-20 Monocyclic or polycyclic aryl-substituted or unsubstituted phenyl groups; via deuteration or C 6-20 Monocyclic or polycyclic aryl-substituted or unsubstituted biphenyls; via deuteration or C 6-20 Monocyclic or polycyclic aryl-substituted or unsubstituted triphenyl; via deuteration or C 6-20Monocyclic or polycyclic aryl-substituted or unsubstituted naphthyl groups; via deuteration or C 6-20 Monocyclic or polycyclic aryl-substituted or unsubstituted phenanthrene groups; deuterated or C 6-30 Monocyclic or polycyclic aryl substituted or unsubstituted thiophene group; via C 6-20 Monocyclic or polycyclic aryl-substituted or unsubstituted dibenzofuranyl; via C 6-20 Monocyclic or polycyclic aryl substituted or unsubstituted naphthobenzofuranyl; via C 6-20 Monocyclic or polycyclic aryl-substituted or unsubstituted dibenzothiophene; or via C 6-20 Naphthobenzothiophene group, which is monocyclic or polycyclic aryl substituted or unsubstituted.

[0397] In one exemplary embodiment of this specification, Ar20 and Ar21 may be the same or different, and are independently deuterated or unsubstituted phenyl; deuterated or unsubstituted biphenyl; terphenyl; deuterated or unsubstituted naphthyl; phenyl-substituted or unsubstituted thiophene; phenanthryl; dibenzofuranyl; naphthobenzofuranyl; dibenzothiophene; or naphthobenzothiophene.

[0398] In one exemplary embodiment of this specification, R301 is hydrogen; deuterium; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group.

[0399] In one exemplary embodiment of this specification, R301 is hydrogen; deuterium; or deuterium- or C-terminated. 6-30 Monocyclic or polycyclic aryl groups, or combinations thereof, substituted or unsubstituted C 6-30 Monocyclic or polycyclic aryl groups; or C groups that are deuterated or unsubstituted. 2-30 Monocyclic or polycyclic heteroaryl groups.

[0400] In one exemplary embodiment of this specification, R301 is hydrogen; deuterium; a phenyl group substituted with or unsubstituted with deuterium, phenyl, naphthyl or a combination thereof; a biphenyl group substituted with deuterium; a naphthyl group substituted with or unsubstituted with deuterium, phenyl, naphthyl or a combination thereof; a dibenzofuranyl group substituted with or unsubstituted with deuterium; or a dibenzothiophenyl group substituted with or unsubstituted with deuterium.

[0401] In one exemplary embodiment of this specification, R301 is hydrogen.

[0402] In one exemplary embodiment of this specification, R301 is deuterium.

[0403] According to an exemplary embodiment of this specification, chemical formula H is one of the following compounds:

[0404]

[0405]

[0406]

[0407]

[0408]

[0409]

[0410]

[0411]

[0412]

[0413]

[0414] According to an exemplary embodiment of this specification, the first body and the second body may be deposited on the luminescent layer in a bilayer, co-deposition, or premixed manner.

[0415] According to one exemplary embodiment of this specification, the second body can be used as the superfluorescent (or triple-sensitized fluorescent) body of the luminescent layer.

[0416] When the emissive layer emits red light, phosphorescent materials such as PIQIr(acac) (bis(1-phenylisoquinoline)acetylacetone iridium), PQIr(acac) (bis(1-phenylquinoline)acetylacetone iridium), PQIr (tris(1-phenylquinoline)iridium), and PtOEP (octaethylporphyrin platinum) can be used as the luminescent dopant; or fluorescent materials such as Alq3 (tris(8-hydroxyquinoline)aluminum), but not limited thereto. When the emissive layer emits green light, phosphorescent materials such as Ir(ppy)3 (planar-tris(2-phenylpyridine)iridium) can be used as the luminescent dopant; or fluorescent materials such as Alq3 (tris(8-hydroxyquinoline)aluminum), but not limited thereto. When the luminescent layer emits blue light, phosphorescent materials, such as (4,6-F2ppy)2Irpic, or fluorescent materials, such as spiro-DPVBi, spiro-6P, stilbene (DSB), stilbene arylene (DSA), PFO-based polymers, and PPV-based polymers, can be used as luminescent dopants, but are not limited thereto.

[0417] In the organic light-emitting devices described in this specification, boron-containing polycyclic compounds, Pt-containing compounds, or Ir complexes can be used as light-emitting dopants, but are not limited to these.

[0418] In the organic light-emitting device described in this specification, the light-emitting layer comprises a compound of chemical formula 1 as the main body, and may also contain dopants.

[0419] In the organic light-emitting devices described in this specification, the dopant can be a compound with the chemical formula D.

[0420] [Chemical formula D]

[0421]

[0422] In chemical formula D,

[0423] X1 and X2 may be the same or different, independently CR', NR", or O, and at least one of X1 and X2 is NR".

[0424] A and C may be the same or different, and are independently substituted or unsubstituted 5-membered rings; or substituted or unsubstituted 6-membered rings.

[0425] R401, R', and R" may be the same or different, and are independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted silyl group; a substituted or unsubstituted amino group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, or bonded to an adjacent group to form a substituted or unsubstituted ring, and

[0426] r401 is an integer from 0 to 3, and if r401 is 2 or greater, then two or more R401 are the same or different.

[0427] In the organic light-emitting devices described in this specification, A and C may be the same or different, and are independently substituted or unsubstituted hydrocarbon rings; substituted or unsubstituted heterocycles; or their fused rings.

[0428] In the organic light-emitting devices described in this specification, A and C may be the same or different, and are independently hydrocarbon rings substituted with or unsubstituted with alkyl or arylamine groups; or heterocycles substituted with or unsubstituted with alkyl groups.

[0429] In the organic light-emitting devices described in this specification, A and C may be the same or different, and are independently benzene substituted with arylamine or unsubstituted; tetrahydronaphthalene substituted with alkyl or unsubstituted; benzofuran substituted with alkyl or unsubstituted; or benzothiophene substituted with alkyl or unsubstituted.

[0430] In the organic light-emitting devices described in this specification, A and C may be the same or different, and are independently benzene substituted with diphenylamino or unsubstituted; benzofuran substituted with tert-butyl or unsubstituted; benzothiophene substituted with tert-butyl or unsubstituted; or (1,1,4,4)-tetramethyl-(1,2,3,4)-tetrahydronaphthyl.

[0431] In the organic light-emitting devices described in this specification, R401, R' and R” may be the same or different, and are independently hydrogen; deuterium; substituted or unsubstituted alkyl; substituted or unsubstituted cycloalkyl; or substituted or unsubstituted aryl.

[0432] In the organic light-emitting devices described in this specification, R401 represents hydrogen, deuterium, and C. 1-10 Alkyl; or C 6-30 Aryl.

[0433] In the organic light-emitting devices described in this specification, R401 is methyl; tert-butyl; or phenyl.

[0434] In the organic light-emitting devices described in this specification, R” represents a substituted or unsubstituted aryl group.

[0435] In the organic light-emitting devices described in this specification, R” is a substituted or unsubstituted phenyl group; or a substituted or unsubstituted tetrahydronaphthyl group.

[0436] In the organic light-emitting devices described in this specification, R” is a phenyl substituted with or unsubstituted with tert-butyl; a phenyl substituted with phenyl and adamantyl; a biphenyl substituted with or unsubstituted with tert-butyl; or (1,1,4,4)-tetramethyl-(1,2,3,4)-tetrahydronaphthyl.

[0437] In the organic light-emitting devices described in this specification, r401 is 1.

[0438] According to an exemplary embodiment of this specification, chemical formula D is one of the following compounds:

[0439]

[0440] Furthermore, an exemplary embodiment of this specification provides an organic light-emitting device comprising: an anode; a cathode; a first light-emitting layer disposed between the anode and the cathode; and a second light-emitting layer disposed between the first light-emitting layer and the cathode and in contact with the first light-emitting layer, wherein the first light-emitting layer comprises a compound of chemical formula 1, and the second light-emitting layer comprises a compound of chemical formula H.

[0441] An organic light-emitting device according to an exemplary embodiment of this specification includes two or more light-emitting layers, and the different light-emitting layers may respectively contain a compound of chemical formula 1 and a compound of chemical formula H. For example, the light-emitting layers may include a first light-emitting layer containing a compound of chemical formula 1 and a second light-emitting layer containing a compound of chemical formula H. In this case, the second light-emitting layer may be disposed between the first light-emitting layer and the cathode. The first light-emitting layer and the second light-emitting layer may be disposed in contact with each other. When the first light-emitting layer and the second light-emitting layer respectively contain a compound of chemical formula 1 and a compound of chemical formula H as the main components, the first light-emitting layer and the second light-emitting layer also contain dopant compounds. In this case, the first light-emitting layer and the second light-emitting layer may contain the same type of dopant material or may contain different types of dopant materials, but preferably they contain the same type of dopant material.

[0442] In an organic light-emitting device according to an exemplary embodiment of this specification, a second light-emitting layer is disposed between the first light-emitting layer and the cathode.

[0443] An organic light-emitting device according to an exemplary embodiment of this specification is configured such that the first light-emitting layer and the second light-emitting layer are in direct contact. If these configurations are met, the efficiency of the organic light-emitting device can be further improved.

[0444] According to an exemplary embodiment of this specification, chemical formula 1 is the body of the first light-emitting layer.

[0445] According to one exemplary embodiment of this specification, chemical formula H is the host of the second light-emitting layer.

[0446] According to an exemplary embodiment of this specification, the first light-emitting layer and the second light-emitting layer each contain the dopant described above. The dopant may be the same or different.

[0447] According to an exemplary embodiment of this specification, the first light-emitting layer comprises a compound of Formula 1 as the main body and also comprises a dopant material. In this case, based on the total weight of the compound of Formula 1, the dopant material may be included in the first light-emitting layer at a weight ratio (wt%) of about 0.01 wt% to 20 wt% or 0.01 wt% to 10 wt%.

[0448] According to an exemplary embodiment of this specification, the second light-emitting layer comprises a compound of chemical formula H as the main body and also comprises a dopant material. In this case, based on the total weight of the compound of chemical formula H, the dopant material may be included in the second light-emitting layer at a weight ratio (wt%) of about 0.01 wt% to 20 wt% or 0.01 wt% to 10 wt%.

[0449] A hole-blocking (electron control) layer can be disposed between the electron transport layer and the light-emitting layer. The hole-blocking (electron control) layer is a layer that blocks holes from flowing from the light-emitting layer into the cathode and controls the flow of electrons into the light-emitting layer, thereby controlling the overall performance of the device. As a hole-blocking (electron control) material, compounds that prevent holes from flowing from the light-emitting layer into the cathode and have the ability to control the injection of electrons into the light-emitting layer or light-emitting material are preferred. Depending on the composition of the organic layer used in the device, suitable materials can be used as hole-blocking (electron control) materials. Specific examples include, but are not limited to, those mentioned above. Diazole derivatives, triazole derivatives, phenanthrene-rhein derivatives, BCP, aluminum complexes, etc.

[0450] In one exemplary embodiment of this specification, the hole-blocking (electronic control) layer may comprise a compound having a structure in which an N-containing ring is directly or via a linking group connected to spiro[fluorene-9,9'- [Ton] structure.

[0451] The electron transport layer can facilitate electron transport. Materials with high electron mobility that can effectively receive electrons from the cathode and transport them to the luminescent layer are suitable as electron transport materials. Specific examples include, but are not limited to, the compounds mentioned above or Al complexes of 8-hydroxyquinoline; complexes containing Alq3; organic free radical compounds; hydroxyflavonoid-metal complexes; and so on.

[0452] In one exemplary embodiment of this specification, the electron transport layer may comprise a compound containing an N-ring and may also comprise an n-type dopant or an organometallic compound. According to one exemplary embodiment, the compound containing the N-ring may be a triazine-based compound, and the n-type dopant or organometallic compound may specifically be a lithium metal complex compound, such as lithium 8-hydroxyquinoline, and the compound containing the N-ring and the n-type dopant (or organometallic compound) may be included in a weight ratio of 2:8 to 8:2, for example, 4:6 to 6:4.

[0453] According to one exemplary embodiment of this specification, the electronic transport layer may be one or more layers.

[0454] According to an exemplary embodiment of this specification, the electron transport layer consists of two layers, including a first electron transport layer and a second electron transport layer.

[0455] According to one exemplary embodiment of this specification, the electron transport layer comprises a compound represented by the chemical formula ET-1.

[0456] [Chemical formula ET-1]

[0457]

[0458] In the chemical formula ET-1,

[0459] Any one of R601 to R604 is And the others, whether the same or different, are independently hydrogen; deuterium; or cyano.

[0460] r601 to r604 are each integers from 1 to 4, and if r601 to r604 are each 2 or greater, then r601 to r604 are either the same or different.

[0461] L102 is a direct bond; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group.

[0462] l102 is an integer from 1 to 3, and if l102 is 2 or greater, then two or more L102 are the same or different.

[0463] At least one of Z1 to Z3 is N, and the rest are CH, and

[0464] Ar201 and Ar202 may be the same or different, and are independently substituted or unsubstituted aryl groups; or substituted or unsubstituted heteroaryl groups.

[0465] According to an exemplary embodiment of this specification, R601 to R604 are not... The others may be the same or different, and are independently hydrogen; or cyano.

[0466] According to one exemplary embodiment of this specification, L102 is a direct key; or C 6-30 Monocyclic or polycyclic aryl groups.

[0467] According to an exemplary embodiment of this specification, L102 is a direct bond; phenylene; or naphthylene.

[0468] According to one exemplary embodiment of this specification, L102 is a direct key.

[0469] According to one exemplary embodiment of this specification, Ar201 and Ar202 may be identical or different, and are independently C 6-30 Monocyclic or polycyclic aryl groups.

[0470] According to one exemplary embodiment of this specification, Ar201 and Ar202 may be the same or different, and are independently phenyl; biphenyl; or naphthyl.

[0471] According to an exemplary embodiment of this specification, Z1 to Z3 are N.

[0472] According to an exemplary embodiment of this specification, the chemical formula ET-1 is one of the following compounds.

[0473]

[0474] According to an exemplary embodiment of this specification, the electron transport layer includes a first electron transport layer and a second electron transport layer, the first electron transport layer and the second electron transport layer containing a compound of the chemical formula ET-1, and the compound of the chemical formula ET-1 contained in the first electron transport layer and the second electron transport layer are different from each other.

[0475] According to an exemplary embodiment of this specification, the first electron transport layer and the second electron transport layer comprise compounds of the chemical formula ET-1, and the compounds of the chemical formula ET-1 are different from each other.

[0476] The electron transport layer also contains metal complex compounds. These metal complex compounds can be lithium 8-hydroxyquinoline (LiQ), bis(8-hydroxyquinoline)zinc, bis(8-hydroxyquinoline)copper, bis(8-hydroxyquinoline)manganese, tris(8-hydroxyquinoline)aluminum, tris(2-methyl-8-hydroxyquinoline)aluminum, tris(8-hydroxyquinoline)gallium, bis(10-hydroxybenzo[h]quinoline)beryllium, bis(10-hydroxybenzo[h]quinoline)zinc, bis(2-methyl-8-quinoline)gallium chloride, bis(2-methyl-8-quinoline)(o-cresol)gallium, bis(2-methyl-8-quinoline)(1-naphthol)aluminum, bis(2-methyl-8-quinoline)(2-naphthol)gallium, etc., but are not limited to these.

[0477] According to one exemplary embodiment of this specification, the second electron transport layer comprises a compound of formula ET-1 and a metal complex. The compound of formula ET-1 and the metal complex are included in a weight ratio of 1:9 to 9:1, 4:6 to 6:4, or 1:2 to 2:1.

[0478] The electron injection layer can promote electron injection. Preferred electron injection materials include compounds that possess electron transport capabilities, excellent electron injection effects from the cathode, and superior electron injection performance for the luminescent layer or material, preventing excitons generated in the luminescent layer from migrating to the hole injection layer, and exhibiting excellent thin-film formation capabilities. Specifically, these compounds can be fluorenone, anthraquinone dimethyl ether, biphenylquinone, thiam dioxide, etc. azole, diazole, triazole, imidazole Tetracarboxylic acids, fluorenemethane, anthrone, and their derivatives; metal complexes; and nitrogen-containing 5-membered ring derivatives, but not limited thereto.

[0479] The metal complex compounds can be lithium 8-hydroxyquinoline (LiQ), bis(8-hydroxyquinoline)zinc, bis(8-hydroxyquinoline)copper, bis(8-hydroxyquinoline)manganese, tris(8-hydroxyquinoline)aluminum, tris(2-methyl-8-hydroxyquinoline)aluminum, tris(8-hydroxyquinoline)gallium, bis(10-hydroxybenzo[h]quinoline)beryllium, bis(10-hydroxybenzo[h]quinoline)zinc, bis(2-methyl-8-quinoline)chlorogallium, bis(2-methyl-8-quinoline)(o-cresol)gallium, bis(2-methyl-8-quinoline)(1-naphthol)aluminum, bis(2-methyl-8-quinoline)(2-naphthol)gallium, etc., but are not limited to these.

[0480] In one exemplary embodiment of this specification, the electron injection layer may comprise lithium fluoride (LiF).

[0481] In one exemplary embodiment of this specification, the electron injection layer comprises LiQ (lithium 8-hydroxyquinoline).

[0482] Depending on the materials used, the organic light-emitting device according to the present invention can be a front-emitting type, a rear-emitting type, or a dual-sided emitting type.

[0483] Invention Embodiments

[0484] This specification will be described in detail below by way of examples. However, the embodiments according to this specification can be modified in various other forms, and the scope of this application should not be construed as limited to the following embodiments. The embodiments of this specification are provided to illustrate this specification more fully to those skilled in the art.

[0485] <Synthesis example>

[0486] Synthesis example 1.

[0487]

[0488] 1-Chlorinated [substrate] was heated and stirred in a round-bottom flask under a nitrogen atmosphere. (30 g, 114.2 mmol, 1 equivalent) was completely dissolved in 120 mL (1 M) dichlorobenzene (hereinafter referred to as DCB). After complete dissolution, trifluoromethanesulfonic acid-d (hereinafter referred to as TfOD, 20 equivalent, 202 mL) was added, and the mixture was heated at 130 °C and stirred for 2 hours. After the reaction was complete, the temperature was lowered. The aqueous layer was then removed, and the solution was washed with an aqueous solution of NaHCO3 to determine that the pH was neutral. The organic layer was collected, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized under toluene / EtOH conditions to prepare compound M-1 (21.7 g, 70%).

[0489] As a result of the mass analysis of compound M-1, the deuterium substitution rate was approximately 90%.

[0490] MS [M+H] + =273.

[0491] Synthesis example 2.

[0492]

[0493] Compounds M-1 (8 g, 29.41 mmol, 1 equivalent) and M-2 (8.5 g, 1.1 equivalent) were dissolved in 320 mL (0.1 M) of 1,4-dioxanone in a round-bottom flask under a nitrogen atmosphere. The mixture was stirred in alkane. Even if the compound was not completely dissolved, an aqueous solution of K3PO4 (12.5 g in 80 mL of H2O, 2 equivalents) was added. After adding bis(tri-tert-butylphosphine)palladium(0) (0.15 g, 1 mol%), the mixture was heated and stirred for 2 hours. The temperature was lowered to room temperature, and the solid was obtained by filtration under reduced pressure. The obtained solid was dissolved in toluene and then washed with water. After removing the aqueous layer, drying with anhydrous magnesium sulfate, and concentrating under reduced pressure, compound C-1 (8.7 g, 65%) was prepared by recrystallization under toluene conditions.

[0494] MS [M+H] + =455.

[0495] Synthesis example 3.

[0496]

[0497] Compound C-18 was synthesized in the same manner as in Synthesis Example 2 using M-1 (8 g, 1 equivalent) and M-3 as starting materials. Compound C-18 (8.0 g, 52%) was prepared by recrystallization under toluene conditions.

[0498] MS [M+H] + =521.

[0499] Synthesis example 4.

[0500]

[0501] Compounds M-4 (90% deuterium substitution, 10 g, 28.57 mmol, 1 equivalent) and M-5 (4 g, 1.1 equivalent) were dissolved in 200 mL (0.15 M) of 1,4-dioxane in a round-bottom flask under a nitrogen atmosphere. The mixture was stirred in alkane. Even if the compound was not completely dissolved, an aqueous solution of K₂CO₃ (7.9 g in 50 mL of H₂O, 2 equivalents) was added. After adding tetrakis(triphenylphosphine)palladium(0) (0.33 g, 1 mol%), the mixture was heated and stirred for 3 hours. The temperature was lowered to room temperature. After adding an equal amount of ethanol as the solvent, the mixture was stirred. A solid was obtained by filtration under reduced pressure. The obtained solid was dissolved in toluene and then washed with water. After removing the aqueous layer, drying with anhydrous magnesium sulfate, and concentrating under reduced pressure, compound M-6 (8.3 g, 83%) was prepared by recrystallization under toluene / ethanol conditions.

[0502] MS [M+H] + =353.

[0503] Synthesis example 5.

[0504]

[0505] Compound C-21 was synthesized using M-6 (7 g, 1 equivalent) and M-7 as starting materials in the same manner as in Synthesis Example 2. Compound C-21 (5.2 g, 47%) was prepared by recrystallization under toluene conditions.

[0506] MS [M+H] + =561.

[0507] Synthesis example 6.

[0508]

[0509] Compound M-8 was synthesized using M-4 (7 g, 1 equivalent) and M-2 as starting materials in the same manner as in Synthesis Example 4. Compound M-8 (5.2 g, 47%) was prepared by recrystallization under toluene / ethanol conditions.

[0510] Compound C-23 was synthesized using M-8 (7 g, 1 equivalent) and M-9 as starting materials in the same manner as in Synthesis Example 2. Compound C-23 (5.9 g, 61%) was prepared by recrystallization under toluene conditions.

[0511] MS [M+H] + =670.

[0512] Synthesis example 7.

[0513]

[0514] Compound M-12 was synthesized using M-10 (10 g, 1 equivalent) and M-11 as starting materials in the same manner as in Synthesis Example 4. Compound M-12 (8.9 g, 73%) was prepared by recrystallization under toluene / ethanol conditions.

[0515] Compound C-8 was synthesized in the same manner as in Synthesis Example 2 using M-12 (8 g, 1 equivalent) and M-13 (40% deuterium substitution) as starting materials. Compound C-8 (4.3 g, 33%) was prepared by recrystallization under toluene / ethyl acetate conditions.

[0516] MS [M+H] + =683.

[0517] Synthesis example 8.

[0518]

[0519] Use 1-chloro Compound C-6 was synthesized in the same manner as in Synthesis Example 2 using M-14 (41% deuterium substitution) and M-14 (10 g, 1 equivalent) as starting materials. Compound C-6 (14 g, 61%) was prepared by recrystallization under toluene conditions.

[0520] MS [M+H] + =521.

[0521] Synthesis example 9.

[0522]

[0523] Compound M-17 was synthesized using M-15 (5 g, 1 equivalent) and M-16 as starting materials in the same manner as in Synthesis Example 4. Compound M-17 (5.9 g, 78%) was prepared by recrystallization under toluene / ethyl acetate conditions.

[0524] MS [M+H] + =621.

[0525] Compound C-7 was synthesized in the same manner as in Synthesis Example 2 using M-17 (8 g, 1 equivalent) and M-5 (95% or higher deuterium substitution) as starting materials. Compound C-7 (2.9 g, 54%) was prepared by recrystallization under toluene conditions.

[0526] MS [M+H] + =668.

[0527] Synthesis example 10.

[0528]

[0529] Compound C-20 was synthesized using M-18 (7 g, 1 equivalent) and M-19 as starting materials in the same manner as in Synthesis Example 2. Compound C-20 (8.7 g, 81%) was prepared by recrystallization under toluene conditions.

[0530] MS [M+H] + =526.

[0531] Synthesis example 11.

[0532]

[0533] Use 2-chloro Compound M-20 was synthesized using 30 g (1 equivalent) as the starting material in the same manner as in Synthesis Example 1. Compound M-20 (24.5 g, 79%) was prepared by recrystallization under toluene / ethanol conditions.

[0534] As a result of the mass analysis of compound M-20, the deuterium substitution rate was approximately 90%.

[0535] MS [M+H] + =273.

[0536] Compound C-11 was synthesized in the same manner as in Synthesis Example 2 using M-20 (8 g, 1 equivalent) and M-21 as starting materials. Compound C-11 (9.5 g, 77%) was prepared by recrystallization under toluene conditions.

[0537] MS [M+H] + =421.

[0538] Synthesis example 12.

[0539]

[0540] Use 3-chloro Compound C-2 was synthesized in the same manner as in Synthesis Example 2 using M-22 (10 g, 1 equivalent) and M-22 (64% deuterium substitution) as starting materials. Compound C-2 (11.7 g, 68%) was prepared by recrystallization under toluene conditions.

[0541] MS [M+H] + =452.

[0542] Synthesis example 13.

[0543]

[0544] Use 3-chloro Compound M-24 was synthesized using M-23 as a starting material (10 g, 1 equivalent) and M-23 in the same manner as in Synthesis Example 2. Compound M-24 (14.9, 70%) was prepared by recrystallization under toluene conditions.

[0545] MS [M+H] + =561.

[0546] Compound C-15 was synthesized using M-24 (14 g, 1 equivalent) as the starting material and 30 equivalents of TfOD in the same manner as in Synthesis Example 1. Compound C-15 (3.9 g, 27%) was prepared by recrystallization under toluene conditions.

[0547] As a result of the mass analysis of compound C-15, the deuterium substitution rate was approximately 54%.

[0548] MS [M+H] + =574.

[0549] Synthesis example 14.

[0550]

[0551] Use 6-bromo Compound C-3 was synthesized using d11 (10 g, 1 equivalent, 95% deuterium substitution) and M-25 as starting materials in the same manner as in Synthesis Example 2. Compound C-3 (13.5, 74%) was prepared by recrystallization under toluene conditions.

[0552] MS [M+H] + =581.

[0553] Synthesis example 15.

[0554]

[0555] Use 6-bromo Compound M-27 was synthesized using -d11 (10 g, 1 equivalent, 95% deuterium substitution) and M-26 as starting materials in the same manner as in Synthesis Example 2. Compound M-27 (10.1 g, 88%) was prepared by recrystallization under toluene / ethanol conditions.

[0556] MS [M+H] + =366.

[0557] Synthesis example 16.

[0558]

[0559] Compound M-27 (10 g, 27.3 mmol, 1 equivalent) was dissolved in 140 mL (0.2 M) N,N-dimethylformamide in a round-bottom flask under a nitrogen atmosphere and stirred. After the addition of N-bromosuccinimide (5.4 g, 1.1 equivalent), the mixture was stirred at 40 °C for 6 h. After the reaction was complete, the temperature was lowered to room temperature. After the addition of 70 mL of water and 140 mL of ethanol, the mixture was stirred for 30 min. After filtration, the solid was dissolved in chloroform, washed with aqueous solutions of Na₂S₂O₃ and NaHCO₃, and the aqueous layer was removed. The organic layer was dried with anhydrous magnesium sulfate and concentrated under reduced pressure. Compound M-28 (9.7 g, 80%) was then prepared by recrystallization under toluene / hexane conditions.

[0560] MS [M+H] + =442.

[0561] Synthesis Example 17.

[0562]

[0563] Compound C-9 was synthesized using M-28 (8 g, 1 equivalent) and M-29 as starting materials in the same manner as in Synthesis Example 2. Compound C-9 (5.1 g, 48%) was prepared by recrystallization under toluene conditions.

[0564] MS [M+H] + =588.

[0565] Synthesis example 18.

[0566]

[0567] Use 6-bromo Compound M-31 was synthesized using -d11 (10 g, 1 equivalent, 95% deuterium substitution) and M-30 as starting materials in the same manner as in Synthesis Example 2. Compound M-31 (9.5 g, 77%) was prepared by recrystallization under toluene / hexane conditions.

[0568] MS [M+H] + =391.

[0569] Compound M-32 was synthesized using M-31 (8 g, 1 equivalent) as the starting material in the same manner as in Synthesis Example 16. Compound M-32 (9.1 g, 84%) was prepared by recrystallization under toluene / hexane conditions.

[0570] MS [M+H] + =468.

[0571] Synthesis example 19.

[0572]

[0573] Compound C-14 was synthesized using M-32 (7 g, 1 equivalent) and M-33 as starting materials in the same manner as in Synthesis Example 2. Compound C-14 (3.6 g, 41%) was prepared by recrystallization under toluene conditions.

[0574] MS [M+H] + =672.

[0575] Synthesis example 20.

[0576]

[0577] Use 6-bromo Compound M-34 was synthesized using -d11 (10 g, 1 equivalent, 95% deuterium substitution) and M-5 as starting materials in the same manner as in Synthesis Example 2. Compound M-34 (9.2 g, 91%) was prepared by recrystallization under toluene / hexane conditions.

[0578] MS [M+H] + =320.

[0579] Compound M-35 was synthesized using M-34 (8 g, 1 equivalent) as the starting material in the same manner as in Synthesis Example 16. Compound M-35 (7.9 g, 79%) was prepared by recrystallization under toluene / hexane conditions.

[0580] MS [M+H] + =397.

[0581] Synthesis example 21.

[0582]

[0583] Compound C-17 was synthesized using M-35 (7 g, 1 equivalent) and M-36 as starting materials in the same manner as in Synthesis Example 2. Compound C-17 (2.9 g, 27%) was prepared by recrystallization under toluene conditions.

[0584] MS [M+H] + =617.

[0585] Synthesis example 22.

[0586]

[0587] Use 6-bromo Compound M-38 was synthesized using -d11 (20 g, 1 equivalent, 95% deuterium substitution) and M-37 as starting materials in the same manner as in Synthesis Example 2. Compound M-38 (21.2 g, 80%) was prepared by recrystallization under toluene / hexane conditions.

[0588] MS [M+H] + =421.

[0589] Compound M-39 was synthesized using M-38 (20 g, 1 equivalent) as the starting material in the same manner as in Synthesis Example 16. Compound M-39 (17.5 g, 74%) was prepared by recrystallization under toluene / hexane conditions.

[0590] MS [M+H] + =498.

[0591] Synthesis example 23.

[0592]

[0593] Compound C-22 was synthesized using M-39 (7 g, 1 equivalent) and M-40 as starting materials in the same manner as in Synthesis Example 2. Compound C-22 (3.6 g, 40%) was prepared by recrystallization under toluene conditions.

[0594] MS [M+H] + =644.

[0595] Synthesis example 24.

[0596]

[0597] Compound M-42 was synthesized using M-39 (10 g, 1 equivalent) and M-41 as starting materials in the same manner as in Synthesis Example 2. Compound M-42 (7.8 g, 65%) was prepared by recrystallization under toluene conditions.

[0598] MS [M+H] + =602.

[0599] Compound C-16 was synthesized using M-42 (7 g, 1 equivalent) as the starting material in the same manner as in Synthesis Example 1. Compound C-16 (2.2 g, 31%) was prepared by recrystallization under toluene conditions.

[0600] As a result of the mass analysis of compound C-16, the deuterium substitution rate was approximately 71%.

[0601] MS [M+H] + =610.

[0602] Synthesis example 25.

[0603]

[0604] Compound M-44 was synthesized in the same manner as in Synthesis Example 16 using M-43 (10 g, 1 equivalent, 45% deuterium substitution) as the starting material. Compound M-44 (11.2 g, 89%) was prepared by recrystallization under toluene / ethanol conditions.

[0605] MS [M+H] + =388.

[0606] Compound C-4 was synthesized using M-44 (10 g, 1 equivalent) and M-2 as starting materials in the same manner as in Synthesis Example 2. Compound C-4 (7.7 g, 57%) was prepared by recrystallization under toluene conditions.

[0607] MS [M+H] + =526.

[0608] Synthesis example 26.

[0609]

[0610] Compound M-46 was synthesized using M-45 (10 g, 1 equivalent, 50% deuterium substitution) as the starting material in the same manner as in Synthesis Example 16. Compound M-46 (11.3 g, 93%) was prepared by recrystallization under toluene / ethanol conditions.

[0611] MS [M+H] + =439.

[0612] Compound C-12 was synthesized using M-46 (10 g, 1 equivalent) and M-47 as starting materials in the same manner as in Synthesis Example 2. Compound C-12 (6.9 g, 50%) was prepared by recrystallization under toluene conditions.

[0613] MS [M+H] + =603.

[0614] Synthesis example 27.

[0615]

[0616] Compound M-49 was synthesized using M-48 (10 g, 1 equivalent) as the starting material in the same manner as in Synthesis Example 16. Compound M-49 (9.8 g, 82%) was prepared by recrystallization under toluene / hexane conditions.

[0617] MS [M+H] + =483.

[0618] Compound M-50 was synthesized using M-49 (9 g, 1 equivalent) and M-2 as starting materials in the same manner as in Synthesis Example 2. Compound M-50 (7.6 g, 66%) was prepared by recrystallization under toluene conditions.

[0619] MS [M+H] + =621.

[0620] Synthesis example 28.

[0621]

[0622] Compound C-5 was synthesized using M-50 (7 g, 1 equivalent) as the starting material and 30 equivalents of TfOD in the same manner as in Synthesis Example 1. Compound C-5 (2.7 g, 38%) was prepared by recrystallization under toluene conditions.

[0623] As a result of the mass analysis of compound C-5, the deuterium substitution rate was approximately 71%.

[0624] MS [M+H] + =636.

[0625] Synthesis example 29.

[0626]

[0627] 6,12-dibromodiphenyl ether was subjected to nitrogen atmosphere. (15 g, 38.85 mmol, 1 equivalent) and M-51 (30.21 g, 2.1 equivalent) were dissolved in 750 mL (0.05 M) of 1,4-dioxanone in a round-bottom flask. The mixture was stirred in alkane. Even if the compound was not completely dissolved, an aqueous solution of K3PO4 (24.7 g in 180 mL of H2O, 3 equivalents) was added. After adding bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 1 mol%), the mixture was heated and stirred for 4 hours. The temperature was lowered to room temperature, and the solid was obtained by filtration under reduced pressure. The obtained solid was dissolved in xylene and then washed with water. After removing the aqueous layer, drying with anhydrous magnesium sulfate, and concentrating under reduced pressure, compound M-52 (17.6 g, 73%) was prepared by recrystallization under toluene conditions.

[0628] MS [M+H] + =713.

[0629] Compound C-13 was synthesized using M-52 (10 g, 1 equivalent) as the starting material and with 35 equivalents of TfOD and 0.2 M DCB in the same manner as in Synthesis Example 1. Compound C-13 (4.8 g, 41%) was prepared by recrystallization under toluene conditions.

[0630] As a result of the mass analysis of compound C-13, the deuterium substitution rate was approximately 62%.

[0631] MS [M+H] + =733.

[0632] <Test Example 1: Calculation of Triplet Levels>

[0633] Using the TD-DFT (B3LYP) method / 6-31G Basis set methods are used to calculate the HOMO, LUMO, singlet, and triplet energy levels of the absorption states of the following compounds. Calculation results are identical for hydrogen (H) and deuterium (D) structures.

[0634] The results of calculating the HOMO, LUMO, singlet, and triplet energy levels of the following compounds are shown in Table 1 below.

[0635]

[0636] [Table 1]

[0637]

[0638] The relative values ​​of triplet energy levels for compounds with various functional groups (compounds A1 to A15) were investigated. As shown in Table 1, it was found that the triplet energy level of a compound is determined by the functional group in the compound that has the lowest triplet energy level.

[0639] The triplet energies of compounds B-1 to B-3 and X-4 were determined by compound A-1. Compounds X-2 and X-3, possessing the functional group A-4, exhibited the lowest triplet energy levels, similar to the T1 values ​​of A-4. Because compound B-4 has a triplet energy ratio... With higher functional groups, it can be expected that the triplet state energy of B-4 will be determined by compounds A-5 and A-6, which have similar values.

[0640] Furthermore, although the T1 values ​​of compounds A-9 and A-13 are lower than those of compound A-4, compounds A-9 and A-13 have similar values ​​that are 0.2 eV or less lower than the triplet energy level of compound A-4. Therefore, the T1 values ​​of compounds X-1, X-5, and X-8 are close to those of compounds X-2 and X-3, which are affected by compound A-4.

[0641] <Test Example 2: Fabrication of Organic Light-Emitting Devices>

[0642] Example 1-1

[0643] A glass substrate coated with 1,400 Å thick indium tin oxide (ITO) was immersed in distilled water containing a cleaning agent and then ultrasonically cleaned. A Fischer Co. product was used as the cleaning agent. Distilled water, filtered twice through a Millipore Co. filter, was used. After washing the ITO for 30 minutes, the substrate was ultrasonically cleaned twice for 10 minutes each time with distilled water. Following the distilled water wash, the glass substrate was ultrasonically cleaned using isopropanol, acetone, and methanol as solvents, dried, and then transferred to a plasma cleaner. Additionally, the substrate was cleaned with oxygen plasma for 5 minutes before being transferred to a vacuum evaporation machine.

[0644] A hole injection layer was formed on the ITO transparent electrode prepared as described above by vacuum deposition of compounds HT-A and HI-A to a thickness of 110 Å at a weight ratio of 90:10. A hole transport layer was formed on the hole injection layer by vacuum deposition of HT-A to a thickness of 1000 Å. An electron blocking layer was formed on the hole transport layer by vacuum deposition of HT-B to a thickness of 50 Å. Next, a light-emitting layer was formed on the electron blocking layer by co-depositing compound C-4 and blue fluorescent dopant BD-2 to a thickness of 200 Å at a weight ratio of 97:3 (wt%). Next, a first electron transport layer was formed on the light-emitting layer by vacuum deposition of compound ET-A to a thickness of 50 Å, followed by vacuum deposition of ET-B and LiQ to a thickness of 300 Å. An electron injection layer was formed on the second electron transport layer by vacuum deposition of LiQ to a thickness of 5 Å. The cathode was formed by depositing aluminum and silver to a thickness of 220 Å on an electron injection layer in a weight ratio of 10:1, followed by depositing aluminum to a thickness of 1000 Å on top of that layer.

[0645] In the above process, the deposition rate of the organic material was maintained between 0.4 Å / s and 0.9 Å / s, the deposition rate of aluminum at the cathode was maintained at 2 Å / s, and the vacuum level during deposition was maintained at 1 × 10⁻⁶. -7 Up to 5×10 -8 To prepare organic light-emitting devices.

[0646]

[0647] Examples 1-2 to 1-5

[0648] Organic light-emitting devices of Examples 1-2 to 1-5 were prepared using the same method as in Examples 1-1, except that the host compounds described in Table 2 were used instead of the light-emitting layer materials in Examples 1-1.

[0649] Comparative Examples 1-1 to 1-3

[0650] Organic light-emitting devices of Comparative Examples 1-1 to 1-3 were prepared using the same method as in Examples 1-1, except that the host compounds described in Table 2 were used instead of the light-emitting layer materials in Examples 1-1.

[0651] Table 2 shows the main components used in the luminescent layer. At 10 mA / cm² 2 The operating voltage, luminous efficiency (EQE), and maximum emission wavelength (EL-maximum) of the organic light-emitting device thus fabricated were measured at a current density of 20 mA / cm². 2 The time taken to reach 95% of the initial brightness at the given current density is taken as a relative value (lifetime ratio) relative to Comparative Examples 1-3.

[0652]

[0653] [Table 2]

[0654]

[0655] As shown in Table 2, in Comparative Examples 1-1 and 1-2, the use of [materials] having the same chemical formula as described in this specification was investigated. The performance of organic light-emitting devices based on compounds with different triplet energies (A-4, 2.5 eV) was investigated. Compounds with triplet energies higher than (A-4, 2.5 eV) were also studied. Compound B-7, with a phenanthrene (A-5, 2.74 eV) substituent, and compounds with triplet energy below [missing value] The performance of compound B-6, which has a pyrene (A-3, 2.12 eV) substituent, was compared. Comparative Examples 1-2, which use compound B-7, were inferior to Examples 1-1 to 1-5, which use compounds of this specification, in both efficiency and lifetime.

[0656] Compared with Examples 1-1 to 1-5, which used compounds of this specification, Comparative Example 1-1, which used compound B-6, showed similar efficiency and lifetime, but had the problem that the maximum emission wavelength of the organic light-emitting device was long, and therefore the color purity of the blue light emission was reduced.

[0657] Furthermore, comparing Examples 1-1 to 1-5 of this specification with Comparative Examples 1-3, it was determined that the lifetime of Examples 1-1 to 1-5 was improved compared with Comparative Examples 1-3, which can be attributed to the effect of deuterium substitution.

[0658] <Test Example 3: Fabrication of Organic Light-Emitting Devices>

[0659] Example 2-1

[0660] A glass substrate coated with 1,400 Å thick indium tin oxide (ITO) was immersed in distilled water containing a cleaning agent and then ultrasonically cleaned. A Fischer Co. product was used as the cleaning agent. Distilled water, filtered twice through a Millipore Co. filter, was used. After washing the ITO for 30 minutes, the substrate was ultrasonically cleaned twice for 10 minutes each time with distilled water. Following the distilled water wash, the glass substrate was ultrasonically cleaned using isopropanol, acetone, and methanol as solvents, dried, and then transferred to a plasma cleaner. Additionally, the substrate was cleaned with oxygen plasma for 5 minutes before being transferred to a vacuum evaporation machine.

[0661] A hole injection layer was formed on the ITO transparent electrode prepared as described above by vacuum deposition of compounds HT-A and HI-A to a thickness of 110 Å at a weight ratio of 90:10. A hole transport layer was formed on the hole injection layer by vacuum deposition of HT-A to a thickness of 1000 Å. An electron blocking layer was formed on the hole transport layer by vacuum deposition of HT-B to a thickness of 50 Å. Next, a first emitting layer was formed by co-depositing the substrate of the first emitting layer shown in Table 3 and the blue fluorescent dopant BD-1 at a weight ratio of 95:5 (wt%), and a second emitting layer was formed by co-depositing the substrate of the second emitting layer and the blue fluorescent dopant BD-1 at a weight ratio of 95:5 (wt%).

[0662] The thicknesses of the first and second luminescent layers are shown in Table 3. The sum of the thicknesses of the two luminescent layers is 250 Å. Next, compound ET-A to a thickness of 50 Å is vacuum-deposited on the luminescent layers as a first electron transport layer, followed by the formation of a second electron transport layer of 300 Å thickness by vacuum deposition of ET-B and LiQ at a weight ratio of 2:1. An electron injection layer is formed by vacuum deposition of LiQ to a thickness of 5 Å on the second electron transport layer. A cathode is formed by depositing aluminum and silver to a thickness of 220 Å at a weight ratio of 10:1 on the electron injection layer, followed by the deposition of aluminum to a thickness of 1000 Å.

[0663] In the above process, the deposition rate of the organic material was maintained between 0.4 Å / s and 0.9 Å / s, the deposition rate of aluminum at the cathode was maintained at 2 Å / s, and the vacuum level during deposition was maintained at 1 × 10⁻⁶. -7 Up to 5×10 -8 To prepare organic light-emitting devices.

[0664]

[0665] Examples 2-2 to 2-14, 2-19, 2-22 and 2-23

[0666] The organic light-emitting devices of Examples 2-2 to 2-14 and 2-19 were manufactured using the same method as in Example 2-1, except that the host and dopant compounds described in Table 3 were used instead of the light-emitting layer material of Example 2-1.

[0667] Examples 2-15 to 2-18

[0668] The organic light-emitting devices of Examples 2-15 to 2-18 were manufactured using the same method as in Example 2-1, except that the host and dopant compounds described in Table 3 were used instead of the light-emitting layer material of Example 2-1, and specifically, B-1 and B-2 were co-deposited in a 1:1 weight ratio (wt%) as a second host to replace compound B-2.

[0669] Examples 2-20 to 2-21

[0670] The organic light-emitting devices of Examples 2-20 to 2-21 were manufactured using the same method as in Example 2-1, except that the host and dopant compounds described in Table 3 were used instead of the light-emitting layer material of Example 2-1, and specifically, two types of compounds were co-deposited as the first host in a 1:1 weight ratio (wt%).

[0671] Comparative Examples 2-1 to 2-9

[0672] Organic light-emitting devices of Comparative Examples 2-1 to 2-9 were prepared using the same method as in Example 2-1, except that the host and dopant compounds described in Table 3 were used instead of the light-emitting layer material of Example 2-1.

[0673]

[0674]

[0675]

[0676] Table 3 shows the compounds used in the luminescent layer. At 10 mA / cm² 2 The operating voltage and conversion efficiency (cd / A / y) of the organic light-emitting device prepared from the compound were measured at a current density of 20 mA / cm². 2 The time taken to reach 95% of the initial brightness at the given current density is taken as a relative value (lifetime ratio) relative to Comparative Example 2-1.

[0677] Conversion efficiency (cd / A / y) takes into account the material’s current efficiency (cd / A) and color purity (CIEy), and is an important reference value for the efficiency of OLED devices that aim for high brightness and high color reproducibility.

[0678] [Table 3]

[0679]

[0680]

[0681] As can be seen from Table 3, in organic light-emitting devices comprising two light-emitting layers, at least one compound of Formula 1 is used as the host of the first light-emitting layer. It was determined that, compared to using only anthracene-based compounds as the blue host, an organic light-emitting device comprising a compound of Formula 1 according to an exemplary embodiment of this specification has higher luminous efficiency and lifetime.

[0682] Comparative Examples 2-4 and 2-5 revealed that anthracene-based compounds and The location of compounds has a significant impact on device performance. When a B-5 compound with a low triplet state energy is present in the region where holes and electrons are bound, the resulting triplet state cannot transfer energy to the higher-energy X-7 and accumulates in B-5, which adversely affects the device lifetime.

[0683] In addition, comparative examples 2-8 were identified. The device performance of the compound (in which carbazole other than that of formula 2 is present in formula 1) is inferior to that of the organic light-emitting device containing formula 1 of this specification.

[0684] Furthermore, as determined by Comparative Examples 2-4 and 2-9, deuterium substitution significantly increases lifetime, as shown in the results in Table 2 above.

Claims

1. A compound of chemical formula 1: [Chemical Formula 1] In chemical formula 1, At least one of R1 to R12 is of formula 2, and the remaining R1 to R12 that are not of formula 2 are the same or different, and are independently hydrogen; deuterium; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group. [Chemical Formula 2] In chemical formula 2, Y1 is either O or S. L1 is a direct bond; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group. l1 is either 1 or 2, and if l1 is 2, then L1 is either the same or different. G1 through G3 may be the same or different, and are independently hydrogen; deuterium; deuterated or unsubstituted phenyl; deuterated or unsubstituted biphenyl; deuterated or unsubstituted naphthyl; deuterated or unsubstituted phenanthryl; or deuterated or unsubstituted C 5-20 Mixed aromatics, g1 to g3 are each an integer from 1 to 4. If g1 is 2 or greater, then two or more G1 values ​​are the same or different. If g2 is 2 or greater, then two or more G2 values ​​are either the same or different. If g3 is 2 or greater, then two or more G3s are the same or different. m is 0 or 1. If m is 0, then g2 is an integer from 1 to 4 and g1 + g2 ≤ 7. If m is 1, then g2 is 1 or 2 and g1 + g2 + g3 ≤ 9. For the portion bonded to chemical formula 1, and Chemical formula 1 contains at least one deuterium.

2. The compound according to claim 1, wherein the substituted or unsubstituted aryl group, the substituted or unsubstituted heteroaryl group, the substituted or unsubstituted arylene group, the substituted or unsubstituted heteroaryl group, and the triplet energy level (T) of formula 2 are present. s 1) equal to or higher than The triplet energy level.

3. The compound according to claim 1, wherein the substituted or unsubstituted aryl group, the substituted or unsubstituted heteroaryl group, the substituted or unsubstituted arylene group, the substituted or unsubstituted heteroaryl group, and the triplet energy level (T) of formula 2 are present. s 1) lower than The triplet energy level, and T s 1 and The energy difference between the triplet levels is greater than 0 eV and equal to or less than 0.2 eV.

4. The compound according to claim 1, wherein chemical formula 1 is any one of chemical formulas 1-1 to 1-6: [Chemical Formula 1-1] [Chemical Formula 1-2] [Chemical Formulas 1-3] [Chemical Formulas 1-4] [Chemical Formulas 1-5] [Chemical Formulas 1-6] In chemical formulas 1-1 to 1-6, Y1, L1, l1, G1 to G3 and g1 to g3 are the same as those defined in chemical formula 2. R1 to R12 may be the same or different, and are independently hydrogen; deuterium; substituted or unsubstituted aryl; or substituted or unsubstituted heteroaryl. Y11 is either O or S. L11 is a direct bond; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group. l11 is either 1 or 2, and if l11 is 2, then L11 is either the same or different. G11 to G13 may be the same or different, and are independently hydrogen; deuterium; deuterated or unsubstituted phenyl; deuterated or unsubstituted biphenyl; deuterated or unsubstituted naphthyl; deuterated or unsubstituted phenanthryl; or deuterated or unsubstituted C 5-20 Mixed aromatics, g11 to g113 are each an integer from 1 to 4. If g11 is 2 or greater, then two or more G11 values ​​are the same or different. If g12 is 2 or greater, then two or more G12 values ​​are the same or different. If g13 is 2 or greater, then two or more G13s are the same or different. m' is 0 or 1. If m' is 0, then g12 is an integer from 1 to 4, and g11 + g12 ≤ 7, and If m' is 1, then g12 is 1 or 2, and g11+g12+g13≤9.

5. The compound according to claim 1, wherein chemical formula 2 is any one of chemical formulas 2-1 to 2-7: [Chemical Formula 2-1] [Chemical Formula 2-2] [Chemical Formula 2-3] [Chemical Formula 2-4] [Chemical Formula 2-5] [Chemical Formula 2-6] [Chemical Formula 2-7] In chemical formulas 2-1 to 2-7, Y1, L1, l1, G1 to G3 and g1 to g3 are the same as those defined in Chemical Formula 2.

6. The compound according to claim 1, wherein at least one of R1 to R12 is of formula 2, and the remaining R1 to R12 that are not of formula 2 are the same or different, and are independently hydrogen; deuterium; a phenyl substituted with or unsubstituted with deuterium, phenyl, biphenyl, naphthyl or a combination thereof; a biphenyl substituted with or unsubstituted with deuterium, phenyl or a combination thereof; a terphenyl substituted with or unsubstituted with deuterium; a naphthyl substituted with or unsubstituted with deuterium, phenyl, naphthyl or a combination thereof; or a phenanthrene substituted with or unsubstituted with deuterium.

7. The compound according to claim 1, wherein L1 is a direct bond; a phenylene substituted with or unsubstituted with deuterium, biphenyl, naphthyl or a combination thereof; a biphenylene substituted with or unsubstituted with deuterium, phenyl or a combination thereof; or a terphenylene substituted with or unsubstituted with deuterium.

8. The compound according to claim 1, wherein G1 to G3 are the same or different, and are independently hydrogen; deuterium; a deuterated or unsubstituted phenyl; a deuterated or unsubstituted biphenyl; a deuterated or unsubstituted naphthyl; a deuterated or unsubstituted phenanthryl; a deuterated or unsubstituted benzofuranyl; a deuterated or unsubstituted dibenzofuranyl; a deuterated or unsubstituted benzothiophenyl; or a deuterated or unsubstituted dibenzothiophenyl.

9. The compound according to claim 1, wherein chemical formula 1 is one of the following compounds: 。 10. An organic light-emitting device, comprising: anode; cathode; as well as One or more organic layers are disposed between the anode and the cathode. At least one of the organic layers comprises a compound according to any one of claims 1 to 9.

11. The organic light-emitting device of claim 10, wherein the organic layer comprises a light-emitting layer, and the light-emitting layer contains the compound.

12. The organic light-emitting device according to claim 11, wherein the light-emitting layer comprises the compound as a host.

13. The organic light-emitting device of claim 11, wherein the light-emitting layer comprises the compound as a host and further comprises a dopant.

14. The organic light-emitting device according to claim 13, wherein the dopant is a compound of chemical formula D: [Chemical formula D] In chemical formula D, X1 and X2 may be the same or different, independently CR', NR", or O, and at least one of X1 and X2 is NR". A and C may be the same or different, and are independently substituted or unsubstituted 5-membered rings; or substituted or unsubstituted 6-membered rings. R401, R', and R" may be the same or different, and are independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted silyl group; a substituted or unsubstituted amino group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, or bonded to an adjacent group to form a substituted or unsubstituted ring, and r401 is an integer from 0 to 3, and if r401 is 2 or greater, then two or more R401 are the same or different.

15. The organic light-emitting device of claim 11, wherein the light-emitting layer comprises the compound as a first host and further comprises a second host.

16. The organic light-emitting device according to claim 15, wherein the second host is a compound of chemical formula H: [Chemical formula H] In the chemical formula H, L20 and L21 may be the same or different, and are independently direct bonds; substituted or unsubstituted aryl groups; or substituted or unsubstituted divalent heterocyclic groups. Ar20 and Ar21 may be the same or different, and are independently hydrogen; deuterium; substituted or unsubstituted aryl; or substituted or unsubstituted heterocyclic groups. R301 is hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, and r301 is an integer from 1 to 8, and if r301 is 2 or greater, then two or more R301 are the same or different.

17. The organic light-emitting device of claim 11, wherein the light-emitting layer comprises the compound as a first host, further comprises a second host, and further comprises a dopant.

18. An organic light-emitting device, comprising: anode; cathode; A first light-emitting layer is disposed between the anode and the cathode; as well as A second light-emitting layer is disposed between the first light-emitting layer and the cathode and is in contact with the first light-emitting layer. in The first light-emitting layer comprises the compound according to any one of claims 1 to 9, and The second light-emitting layer contains a compound with the chemical formula H: [Chemical formula H] In the chemical formula H, L20 and L21 may be the same or different, and are independently direct bonds; substituted or unsubstituted aryl groups; or substituted or unsubstituted divalent heterocyclic groups. Ar20 and Ar21 may be the same or different, and are independently hydrogen; deuterium; substituted or unsubstituted aryl; or substituted or unsubstituted heterocyclic groups. R301 is hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, and r301 is an integer from 1 to 8, and if r301 is 2 or greater, then two or more R301 are the same or different.

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