Compound for organic electronic element, organic electronic element using same, and electronic device therefor

Abstract

The invention provides an organic electroluminescent element including a first electrode, a second electrode, and an organic material layer between the first electrode and the second electrode, and an electronic device including the element. By mixing the compounds of Chemical Formula 1 to Chemical Formula 3 to be used as a mixed host material of the organic material layer, it is possible to reduce the driving voltage of the organic electroluminescent element and improve the luminous efficiency and lifespan thereof.

Description

Technical Field

[0001] The present invention relates to an organic electroluminescent element and an electronic device thereof using a compound for an organic electroluminescent element, and more particularly to an organic electroluminescent element and an electronic device thereof using a mixture of three or more compounds as a host of a light-emitting layer. Background Art

[0002] Organic light-emitting diodes (OLEDs) are commonly referred to as organic luminescence (OLDs), which convert electrical energy into light energy using organic materials. Organic electroluminescent devices based on this luminescence phenomenon typically include an anode, a cathode, and an organic layer disposed between the anode and cathode. To improve the luminous efficiency and stability of the OLED, the organic layer is typically constructed as a multilayer structure composed of a variety of different organic materials. For example, the organic layer may include multiple sublayers such as a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer.

[0003] In organic electroluminescent devices, the materials used for the organic layer can be divided into luminescent materials and charge transport materials based on their function. Examples include hole injection materials, hole transport materials, electron transport materials, and electron injection materials. Furthermore, luminescent materials can be divided into high-molecular-weight and low-molecular-weight types based on their molecular weight. Furthermore, based on their luminescence mechanism, they can be divided into fluorescent materials (derived from singlet excited states) and phosphorescent materials (derived from triplet excited states). Furthermore, based on the color of their emission, luminescent materials can be divided into blue, green, and red luminescent materials, as well as yellow and orange luminescent materials for achieving natural colors.

[0004] On the other hand, using a single substance as a luminescent material poses the problem of shifting the maximum emission wavelength to longer wavelengths due to intermolecular interactions, and reducing device efficiency due to reduced purity or luminescence attenuation. Therefore, to increase luminous efficiency by increasing purity and transferring energy, a host / dopant system can be used as a luminescent material. The principle is that if a small amount of a dopant with a smaller energy band gap than the host forming the luminescent layer is mixed into the luminescent layer, excitons generated in the luminescent layer are transferred to the dopant, resulting in efficient light emission. In this case, since the wavelength of the host is shifted toward the wavelength band of the dopant, light of a desired wavelength can be obtained depending on the type of dopant used.

[0005] The current portable display market is experiencing a trend of increasing size due to the development of larger displays. This trend is driving the demand for higher power consumption compared to conventional portable displays. Therefore, power consumption has become a crucial factor for portable displays, which rely on a limited power source such as batteries. Efficiency and lifespan are also issues that must be addressed.

[0006] Efficiency, lifespan, and driving voltage are interrelated. As efficiency increases, the driving voltage decreases. This reduces the crystallization of organic materials due to Joule heating during operation, ultimately leading to a longer lifespan. However, simply improving the organic layer alone won't maximize efficiency. This is because achieving both long lifespan and high efficiency is only possible when the energy levels and T1 values between the organic layers, along with the inherent properties of the materials (mobility, surface characteristics, etc.), are optimally combined.

[0007] Therefore, there is an urgent need to develop luminescent materials with high thermal stability and effective charge balance within the luminescent layer. Specifically, to fully exploit the exceptional properties of organic electroluminescent devices, stable and efficient materials must be used to support the various substances that make up the organic layers within the device, such as hole-injection materials, hole-transport materials, luminescent materials, electron-transport materials, and electron-injection materials. Of particular importance is the development of host materials for the luminescent layer. Summary of the Invention

[0008] Technical issues

[0009] An object of the present invention is to provide a compound capable of reducing the driving voltage of a device and improving the luminous efficiency and life, and an organic electroluminescent device and an electronic device using the compound.

[0010] Technical Solution

[0011] In one aspect, the present invention provides an organic electroluminescent device and an electronic device thereof comprising the compound represented by Chemical Formula 1, the compound represented by Chemical Formula 2, and the compound represented by Chemical Formula 3 in a light-emitting layer.

[0012] <Chemical Formula 1> <Chemical Formula 2>

[0013] <Chemical Formula 3>

[0014] Effects of the Invention

[0015] According to the present invention, since the light-emitting layer includes the compounds represented by Chemical Formulas 1 to 3, the driving voltage of the element can be reduced, and the light-emitting efficiency and lifespan can be improved. BRIEF DESCRIPTION OF THE DRAWINGS

[0016] Figures 1 to 3 This is an illustrative diagram of an organic electroluminescent element according to an embodiment of the present invention.

[0017] Description of Reference Signs

[0018] 100, 200, 300: organic electroluminescent element 110: first electrode

[0019] 120: hole injection layer 130: hole transport layer

[0020] 140: Light-emitting layer 150: Electron transport layer

[0021] 160: electron injection layer 170: second electrode

[0022] 180: Light efficiency improvement layer 210: Buffer layer

[0023] 220: Light-emitting auxiliary layer 320: First hole injection layer

[0024] 330: First hole transport layer 340: First light emitting layer

[0025] 350: First electron transport layer 360: First charge generation layer

[0026] 361: Second charge generation layer 420: Second hole injection layer

[0027] 430: Second hole transport layer 440: Second light-emitting layer

[0028] 450: Second electron transport layer CGL: Charge generation layer

[0029] ST1: First stack ST2: Second stack DETAILED DESCRIPTION

[0030] The terms "aryl" and "arylene" as used herein, unless otherwise specified, each have a carbon number of 6 to 60, but are not limited thereto. In the present invention, aryl or arylene encompasses monocyclic rings, ring aggregates, fused polycyclic rings, and spiro compounds.

[0031] The term "fluorenyl" used in the present invention means a substituted or unsubstituted fluorenyl group, and "fluorenylene" means a substituted or unsubstituted fluorenylene group. The fluorenyl or fluorenylene group used in the present invention include spiro compounds formed by mutual bonding between R and R' in the following structure, and also include cyclic compounds formed by mutual bonding between adjacent R". "Substituted fluorenyl" and "substituted fluorenylene" mean that in the following structure, at least one of the substituents R, R', and R" is a substituent other than hydrogen, and R" in the following structure can have a valence of 1 to 8. Regardless of the valence number, fluorenyl and fluorenylene can be named as fluorenylfluorene ring or fluorene in this specification.

[0032]

[0033] The term "spiro compound" as used herein has a "spiro union," which means that two spiro rings are connected by sharing only one atom. In this case, the atom shared by the two rings is called a "spiro atom," and depending on the number of spiro atoms contained in a compound, these are referred to as "monospiro," "bispiro," or "trispiro" compounds, respectively.

[0034] The term "heterocyclic group" as used in the present invention includes not only aromatic rings such as "heteroaryl" or "heteroarylene", but also non-aromatic rings. Unless otherwise specified, it means a ring having 2 to 60 carbon atoms containing one or more heteroatoms, but the present invention is not limited thereto. The term "heteroatom" as used in the present invention, unless otherwise specified, refers to an element other than carbon, such as N, O, S, P, or Si, and may also include compounds containing heteroatom groups such as SO2 and P=O in the following compounds instead of carbon atoms forming the ring. Heterocyclic groups include monocyclic rings, ring aggregates, fused polycyclic rings, and spirocyclic compounds containing heteroatoms.

[0035]

[0036] As used herein, the term "aliphatic cyclic group" refers to cyclic hydrocarbons other than aromatic hydrocarbons, including monocyclic rings, ring aggregates, fused polycyclic rings, and spirocyclic compounds. Unless otherwise specified, this refers to rings with 3 to 60 carbon atoms, but is not limited thereto. For example, a polycyclic ring formed by fusion of an aromatic ring, benzene, and a non-aromatic ring, cyclohexane, is also considered an aliphatic cyclic group.

[0037] The term "haloalkyl", "haloalkyl" or "halogenated alkyl" used in the present invention, unless otherwise specified, refers to an alkyl group substituted by a halogen. For example, it refers to an alkyl group in which some or all of the hydrogen atoms on the alkyl group are substituted by a halogen.

[0038] In this specification, the "group name" corresponding to an aryl group, arylene group, heterocyclic group, etc., shown as examples of each symbol and its substituent, may be described as the "group name reflecting the valence number," but may also be described as the "name of the parent compound." For example, in the case of "phenanthrene," a type of aryl group, the monovalent "group" is "phenanthryl," and the divalent "group" is "phenanthrylene." While the group name may be described by distinguishing the valence number, it may also be described as "phenanthryl," the name of the parent compound, regardless of the valence number. Similarly, in the case of pyrimidine, regardless of the valence number, it may be described as "pyrimidine," or as the "group name" of the corresponding valence number. For example, in the case of a monovalent group, it may be described as "pyrimidinyl," and in the case of a divalent group, it may be described as "pyrimidinylene."

[0039] In addition, when describing the names of compounds or substituents in the present invention, numerals or letters indicating positions may be omitted. For example, pyrido[4,3-d]pyrimidine may be described as pyridopyrimidine, benzofuro[2,3-d]pyrimidine may be described as benzofuropyrimidine, and 9,9-dimethyl-9H-fluorene may be described as dimethylfluorene. Thus, both benzo[g]quinoxaline and benzo[f]quinoxaline may be described as benzoquinoxaline.

[0040] Furthermore, unless otherwise specified, the chemical formulae used in this specification are applicable in the same manner as the definitions of substituents defined by the indices in the following chemical formulae.

[0041]

[0042] When a is an integer of 0, the substituent R 1 In the absence of a, that is, when a is 0, it means that all carbon atoms forming the benzene ring are bonded with hydrogen atoms. In this case, the representation of hydrogen atoms bonded to carbon atoms can be omitted and the chemical formula or compound can be described. 1 Combined with one of the carbon atoms forming the benzene ring, when a is an integer of 2 or 3, respectively, in the following manner, when a is an integer of 4 to 6, in a similar manner, when a is an integer greater than or equal to 2, R 1 They may be the same as or different from each other.

[0043]

[0044] In this specification, unless otherwise specified, "ring" means an aromatic ring, a heteroaromatic ring, a fluorene ring, an aliphatic ring, or the like. "Number" may mean a condensed ring, and "number" may mean a single ring. For example, naphthalene corresponds to a condensed ring with two rings, anthracene to a condensed ring with three rings, thiophene, furan, and the like to a condensed ring with five rings, and benzene and pyridine to a condensed ring with six rings.

[0045] Furthermore, unless otherwise specified in this specification, the ring formed by the bonding of adjacent groups is selected from the group consisting of C6 to C 60 Aromatic ring group; fluorenyl; C2~C containing at least one hetero atom of O, N, S, Si and P 60 Heterocyclic group; and C3~C 60 In this case, the aromatic ring group may be an aromatic ring, and the heterocyclic group may include a heteroaromatic ring.

[0046] Unless otherwise specified, the term "between adjacent groups" in this specification refers not only to groups between R1 and R2, R2 and R3, R3 and R4, and R5 and R6, but also to groups between R7 and R8, which share a common carbon. It also includes substituents bound to non-directly adjacent ring-constituent elements (such as carbon or nitrogen), such as between R1 and R7, R1 and R8, or R4 and R5. Specifically, when directly adjacent ring-constituent elements, such as carbon or nitrogen, have substituents, they are considered adjacent groups. However, if the directly adjacent ring-constituent element has no substituents, the substituent bound to the next ring-constituent element is considered an adjacent group. Furthermore, substituents bound to the same ring-constituent carbon are also considered adjacent groups. In the following chemical formula, when substituents bound to the same carbon, such as R7 and R8, are bonded to form a ring, a compound containing a spirocyclic moiety may be formed.

[0047] ,

[0048] In this specification, the expression 'adjacent groups combine to form a ring' is used synonymously with 'adjacent groups combine to selectively form a ring' and means that at least one pair of adjacent groups combine to form a ring.

[0049] Furthermore, unless otherwise specified in the present specification, substituents such as aryl, arylene, fluorenyl, fluorenylene, heterocyclic, aliphatic cyclic, alkyl, alkenyl, alkynyl, alkoxy, aryloxy, alkylthio, arylthio, and the like, and rings formed by bonding adjacent groups, can be selected from deuterium, halogen, cyano, nitro, siloxane, C6-C 30 an aryl group, a fluorenyl group, a C2 to C3 group containing at least one hetero atom selected from the group consisting of O, N, S, Si and P 30 Heterocyclic group, C3~C 30 Aliphatic ring group, C1~C 20 Alkyl, C2~C 20 Alkenyl, C2~C 20 Alkynyl, C1~C 20 Alkoxy, C6~C 20 Aryloxy, C1~C 20 Alkylthio, C6~C 20 The arylthio group, C1~C 20 Alkyl or C6~C 20 Aryl substituted or unsubstituted silyl, and C1~C 20 Alkyl or C6~C 20The aryl-substituted or unsubstituted phosphine oxide group may be further substituted with one or more substituents selected from the group consisting of the aryl-substituted or unsubstituted phosphine oxide group.

[0050] Below, refer to Figures 1 to 3 , the stacked structure of the organic electroluminescent device including the compound of the present invention is described.

[0051] In assigning reference numerals to the structural elements of the drawings, it is important to note that identical structural elements, even if shown in different drawings, should be assigned the same reference numerals whenever possible. Furthermore, in describing the present invention, detailed descriptions of related known structures or functions may be omitted if it is determined that such detailed descriptions would obscure the gist of the present invention.

[0052] When describing the structural elements of the present invention, terms such as first, second, A, B, (a), and (b) may be used. These terms are used solely to distinguish one structural element from another and do not limit the nature, order, or sequence of the related structural elements. When a structural element is "connected," "coupled," or "coupled" to another structural element, the structural element may be directly connected or coupled to the other structural element, but it can also be understood that there are other structural elements "connected," "coupled," or "coupled" between the structural elements.

[0053] Furthermore, when a structural element such as a layer, film, region, or plate is located "on" or "above" another structural element, this should be understood not only as being "directly above" the other structural element, but also as meaning that there are other structural elements in between. Conversely, when a structural element is located "directly above" another part, it should be understood that there are no other parts in between.

[0054] Figures 1 to 3 This is an illustrative diagram of an organic electroluminescent element according to an embodiment of the present invention.

[0055] Reference Figure 1 The organic electroluminescent element 100 of one embodiment of the present invention includes a first electrode 110 and a second electrode 170 formed on a substrate (not shown), an organic layer located between the first electrode 110 and the second electrode 170, and an inorganic layer located between the first electrode 110 and the second electrode 170.

[0056] For example, the first electrode 110 may be an anode, and the second electrode 170 may be a cathode. In the case of an inverted type, the first electrode may be a cathode, and the second electrode may be an anode.

[0057] The organic layer refers to a layer containing at least one organic substance. For example, the organic layer may include a hole injection layer 120, a hole transport layer 130, a light-emitting layer 140, an electron transport layer 150, and an electron injection layer 160. However, the electron injection layer (160) may also be an inorganic layer that does not contain organic matter.

[0058] Specifically, a hole injection layer 120 , a hole transport layer 130 , a light emitting layer 140 , an electron transport layer 150 , and an electron injection layer 160 may be sequentially formed on the first electrode 110 .

[0059] Preferably, a light efficiency improvement layer 180 may be formed on the side of the first electrode 110 or the second electrode 170 that is not in contact with the organic layer. When the light efficiency improvement layer 180 is formed, the light efficiency of the organic electroluminescent element may be improved.

[0060] For example, a light efficiency improvement layer 180 may be formed on the second electrode 170 . However, in the case of a front-emitting (topemission) organic light-emitting element, the formation of the light efficiency improvement layer 180 may reduce the loss of optical energy caused by SPPs (surface plasma polarizations) in the second electrode 170 . In the case of a back-emitting (bottom-emitting) organic light-emitting element, the light efficiency improvement layer 180 may serve as a buffer for the second electrode 170 .

[0061] A buffer layer 210 or a light-emitting auxiliary layer 220 may be further formed between the hole transport layer 130 and the light-emitting layer 140. Figure 2 Provide explanation.

[0062] Reference Figure 2 According to another embodiment of the present invention, the organic electroluminescent element 200 may include a hole injection layer 120, a hole transport layer 130, a buffer layer 210, a light-emitting auxiliary layer 220, a light-emitting layer 140, an electron transport layer 150, an electron injection layer 160, and a second electrode 170, which are sequentially formed on the first electrode 110, and a light efficiency improvement layer 180 may be formed on the second electrode.

[0063] Although not shown in Figure 2 An electron transport auxiliary layer may also be formed between the light emitting layer 140 and the electron transport layer 150 .

[0064] In addition, according to another embodiment of the present invention, the organic layer may also be in the form of a stack of multiple hole transport layers, light emitting layers, and electron transport layers. Figure 3 Provide explanation.

[0065] Reference Figure 3According to another embodiment of the present invention, the organic electroluminescent element 300 may include two or more stacks of organic layers (ST1, ST2) formed between the first electrode 110 and the second electrode 170, and a charge generation layer CGL may be formed between the stacks of organic layers.

[0066] Specifically, the organic electroluminescent device according to an embodiment of the present invention may include a first electrode 110 , a first stack ST1 , a charge generation layer (CGL), a second stack ST2 , a second electrode 170 , and a light efficiency improvement layer 180 .

[0067] The first stack ST1, as an organic layer formed on the first electrode 110, may include a first hole injection layer 320, a first hole transport layer 330, a first light-emitting layer 340, and a first electron transport layer 350. The second stack ST2 may include a second hole injection layer 420, a second hole transport layer 430, a second light-emitting layer 440, and a second electron transport layer 450. Thus, the first stack and the second stack may have organic layers with the same stacked structure, or may have organic layers with different stacked structures.

[0068] A charge generation layer (CGL) may be formed between the first stack ST1 and the second stack ST2. The charge generation layer (CGL) may include a first charge generation layer 360 and a second charge generation layer 361. The charge generation layer (CGL) is formed between the first light-emitting layer 340 and the second light-emitting layer 440 to increase the efficiency of current generated in each light-emitting layer and smoothly distribute charge.

[0069] Although the first light-emitting layer 340 may include a light-emitting material comprising a blue host and a blue fluorescent dopant, and the second light-emitting layer 440 may include a material comprising a green host doped with a greenish yellow dopant and a red dopant, the materials of the first light-emitting layer 340 and the second light-emitting layer 440 according to the embodiment of the present invention are not limited thereto.

[0070] exist Figure 3 In the embodiment, n may be an integer of 1 to 5. However, when n is 2, a charge generation layer CGL and a third stack may be further stacked on the second stack ST2.

[0071] like Figure 3 By forming multiple light-emitting layers by means of a multi-layer stacking structure, it is possible not only to prepare an organic electroluminescent element that emits white light by means of the mixing effect of the light emitted by each light-emitting layer, but also to prepare an organic electroluminescent element that emits light of multiple colors.

[0072] The compounds represented by Chemical Formulas 1 to 3 of the present invention may be included in an organic layer. For example, the compounds represented by Chemical Formulas 1 to 3 of the present invention may be used as materials for the hole injection layer 120, 320, 420, the hole transport layer 130, 330, 430, the buffer layer 210, the luminescence auxiliary layer 220, the electron transport layer 150, 350, 450, the light emitting layer 140, 340, 440, or the light efficiency improvement layer 180. Preferably, the light emitting layer 140, 340, 440, and / or the light efficiency improvement layer 180 are the materials, and more preferably, the main body of the light emitting layer 140, 340, 440.

[0073] Even for identical or similar cores, the band gap, electrochemical properties, and surface properties may differ depending on which substituent is bonded at which position. Therefore, it is necessary to study the selection of the core and the combination of sub-substituents bonded to it. In particular, when the energy levels and T1 values between the organic layers and the inherent properties of the material (mobility, surface properties, etc.) are optimally combined, long life and high efficiency can be achieved simultaneously.

[0074] Therefore, the compounds represented by Chemical Formulas 1 to 3 in the present invention are used as materials for the light-emitting layers 140, 340, and 440, thereby optimizing the energy levels and T1 values between organic layers, inherent properties (mobility, surface properties, etc.), and improving the lifespan and efficiency of the organic electroluminescent element.

[0075] The organic electroluminescent element of one embodiment of the present invention can be prepared using a variety of evaporation methods. It can be prepared using evaporation methods such as PVD or CVD. For example, the anode 110 can be formed by evaporating a metal or a conductive metal oxide or an alloy thereof on a substrate, and then an organic layer including a hole injection layer 120, a hole transport layer 130, a light-emitting layer 140, an electron transport layer 150, and an electron injection layer 160 is formed thereon, and then a material that can serve as the cathode 170 is evaporated thereon. In addition, a light-emitting auxiliary layer 220 can be formed between the hole transport layer 130 and the light-emitting layer 140, and an electron transport auxiliary layer (not shown) can be formed between the light-emitting layer 140 and the electron transport layer 150. As described above, it can also be formed in a stacked structure.

[0076] Furthermore, the organic layer can be formed into a smaller number of layers using various polymer materials through solvent treatment or solvent purification methods other than vapor deposition, such as spin coating, nozzle printing, inkjet printing, slit coating, dip coating, roll-to-roll, doctor blade coating, screen printing, or thermal transfer. Because the organic layer of the present invention can be formed using a variety of methods, the scope of protection of the present invention is not limited by the formation method.

[0077] The organic electroluminescent device according to one embodiment of the present invention can be classified as a front-emitting type, a rear-emitting type, or a dual-emitting type according to the materials used.

[0078] Furthermore, the organic electroluminescent element according to an embodiment of the present invention may be selected from the group consisting of an organic electroluminescent element, an organic solar cell, an organic photoreceptor, an organic transistor, a monochromatic lighting element, and a quantum dot display element.

[0079] Another embodiment of the present invention may include an electronic device comprising: a display device including the organic electroluminescent element of the present invention; and a control unit for controlling the display device. In this case, the electronic device may be a current or future wireless communication terminal, including all electronic devices such as mobile phones, navigation systems, game consoles, various televisions, and various computers.

[0080] Hereinafter, an organic electroluminescent device according to one aspect of the present invention will be described.

[0081] An organic electroluminescent element according to one aspect of the present invention includes a first electrode, a second electrode, and an organic layer located between the first electrode and the second electrode, wherein the organic layer includes a light-emitting layer, and the light-emitting layer contains a compound represented by the following chemical formula 1, a compound represented by the following chemical formula 2, and a compound represented by the following chemical formula 3.

[0082] Preferably, the host of the light-emitting layer includes compounds represented by Chemical Formula 1 to Chemical Formula 3. For example, the first host may be the compound of Chemical Formula 1, the second host may be the compound of Chemical Formula 2, and the third host may be the compound of Chemical Formula 3. The host may include three or more compounds.

[0083] Hereinafter, the following Chemical Formulas 1 to 3 will be described in detail.

[0084] <Chemical Formula 1> <Chemical Formula 2>

[0085] <Chemical Formula 3>

[0086] In Chemical Formulae 1 to 3, each symbol can be defined as follows.

[0087] Ar 3 to Ar 5 Independently selected from C6~C 60 aryl; fluorenyl; C3~C 60 and containing at least one hetero atom selected from O, N, S, Si and P C2 ~ C30 However, in the chemical formula 2, excluding Ar 3 to Ar 5 In the case where at least one of the following substituents is or contains the following substituents.

[0088]

[0089] In the structure, the C ring, the D ring and the E ring are independently C6 to C 60 aromatic ring, V and W are independently O, S, N (R 11 ) or C (R 12 )(R 13 ), where R 11 to R 13 and are independently selected from hydrogen; deuterium; halogen; cyano; nitro; C6~C 60 aryl; fluorenyl; C2~C containing at least one hetero atom selected from O, N, S, Si and P 60 Heterocyclic group; C3~C 60 Aliphatic ring group; C1~C 20 Alkyl; C2~C 20 Alkenyl; C2~C 20 Alkynyl; C1~C 20 Alkoxy; and C6~C 60 A group composed of aryloxy groups.

[0090] Therefore, in Ar 3 to Ar 5 In the above, for example, a substituent having a heterocyclic group having five or more rings or a fluorene derivative having five or more rings is excluded.

[0091] L 3 To L 5 Independently selected from single bonds; C6~C 60 Arylene; Fluorenylene; C3~C 60 and containing at least one hetero atom selected from O, N, S, Si and P C2 ~ C 30 A group consisting of a heterocyclic group.

[0092] Ar 6 to Ar 8 Independently of each other, C6~C 60 of aromatic groups.

[0093] L 6 To L 8 Independently selected from single bonds; or C6~C 60 arylene group.

[0094] a1 to a6 are independently integers of 0 to 3, and when they are integers of 2 or more, multiple L 3 To multiple L 8 They may be the same or different.

[0095] Ar 20 and Ar 21 Independently selected from C6~C 60 aryl; fluorenyl; C3~C 30 and containing at least one hetero atom selected from O, N, S, Si and P C2 ~ C 60 A group consisting of a heterocyclic group.

[0096] L 20 and L 21 Independently selected from single bonds; C6~C 60 Arylene; Fluorenylene; C3~C 60 and containing at least one hetero atom selected from O, N, S, Si and P C2 ~ C 60 A group consisting of a heterocyclic group.

[0097] R 40 to R 43 independently selected from hydrogen; deuterium; halogen; cyano; nitro; C6~C 60 aryl; fluorenyl; C2~C containing at least one hetero atom selected from O, N, S, Si and P 60 Heterocyclic group; C3~C 60 Aliphatic ring group; C1~C 20 Alkyl; C2~C 20 Alkenyl; C2~C 20 Alkynyl; C1~C 20 Alkoxy; and C6~C 60 The adjacent groups can be combined with each other to form a ring.

[0098] When adjacent groups, for example, adjacent R 40 Between groups, adjacent R 41 Between groups, adjacent R 42 Between groups, adjacent R 43 When the groups are combined to form a ring, the ring can be selected from C6 to C 60 Aromatic ring group; fluorenyl group; C3 to C3 containing at least one hetero atom selected from the group consisting of O, N, S, Si and P 60 Heterocyclic group; and C6~C 60 A group consisting of aliphatic ring groups.

[0099] When the ring formed by the mutual bonding of adjacent groups is an aromatic ring, the aromatic ring may be, for example, C6 to C 20 、C6~C 18 、C6~C 16 、C6~C 14 、C6~C 13 、C6~C 12 、C6~C 10 , C6, C 10 、C 12 、C 14 、C 15 、C 16 、C 18 Specifically, it can form an aromatic ring group of benzene, naphthalene, anthracene, phenanthrene, pyrene, etc.

[0100] When the ring formed by the combination of adjacent groups is a heterocyclic ring, the heterocyclic ring may be, for example, C2 to C 20 、C2~C 19 、C2~C 18 、C2~C 17 、C2~C 16 、C2~C 15 、C2~C 14 、C2~C 13 、C2~C 12 、C2~C 11 、C2~C 10 , C2~C9, C2~C8, C2~C7, C2~C6, C2~C5, C2~C4, C2~C3, C2, C3, C4, C5, C6, C7, C8, C9, C 10 、C 11 、C 12 、C 13 、C 14 、C 15 、C 16 、C 17 、C 18 、C 19 、C 20 and the like, specifically, pyridine, pyrimidine, furan, pyrrole, indole, quinoline, quinazoline, benzoquinazoline, quinoxaline, benzofuran, naphthobenzofuran, dibenzofuran, dinaphthofuran, thiophene, benzothiophene, naphthobenzothiophene, dibenzothiophene, and the like.

[0101] c1 and c4 are integers from 0 to 4, c2 and c3 are integers from 0 to 3, and when they are integers of 2 or more, multiple R 1 To multiple R 4 Same or different respectively.

[0102] In the Ar 3 to Ar 8 、Ar 20 、Ar 21 、R 40 to R 43 When at least one of the aryl groups is an aryl group, the aryl group may be, for example, C6 to C 30 、C6~C 29 、C6~C 28 、C6~C 27 、C6~C 26 、C6~C 25 、C6~C 24 、C6~C 23 、C6~C 22 、C6~C 21 、C6~C 20 、C6~C 19 、C6~C 18 、C6~C 17 、C6~C 16 、C6~C 15 、C6~C 14 、C6~C 13 、C6~C 12 、C6~C 11 、C6~C 10 , C6, C 10 、C 12 、C 13 、C 14 、C 15 、C 16 、C 17 、C 18 Specifically, phenyl, biphenyl, naphthyl, terphenyl, phenanthrene, triphenylene, and the like.

[0103] In the L 3 To L 8 、L 20 、L 21 When at least one of the arylene groups is an arylene group, the arylene group may be, for example, C6 to C 30 、C6~C 29 、C6~C 28 、C6~C 27 、C6~C 26 、C6~C 25 、C6~C 24 、C6~C 23 、C6~C 22、C6~C 21 、C6~C 20 、C6~C 19 、C6~C 18 、C6~C 17 、C6~C 16 、C6~C 15 、C6~C 14 、C6~C 13 、C6~C 12 、C6~C 11 、C6~C 10 , C6, C 10 、C 12 、C 13 、C 14 、C 15 、C 16 、C 17 、C 18 Specifically, phenylene, biphenyl, naphthylene, terphenyl, phenanthrene, triphenylene, and the like.

[0104] In the Ar 3 to Ar 5 、Ar 20 、Ar 21 、L 20 、L 21 、L 3 To L 5 、R 40 to R 43 When at least one of the groups is a heterocyclic group, the heterocyclic group may be, for example, C2 to C 30 、C2~C 29 、C2~C 28 、C2~C 27 、C2~C 26 、C2~C 25 、C2~C 24 、C2~C 23 、C2~C 22 、C2~C 21 、C2~C 20 、C2~C 19 、C2~C 18 、C2~C 17 、C2~C 16 、C2~C 15 、C2~C 14 、C2~C 13 、C2~C 12 、C2~C11 、C2~C 10 , C2~C9, C2~C8, C2~C7, C2~C6, C2~C5, C2~C4, C2~C3, C2, C3, C4, C5, C6, C7, C8, C9, C 10 、C 11 、C 12 、C 13 、C 14 、C 15 、C 16 、C 17 、C 18 、C 19 、C 20 、C 21 、C 22 、C 23 、C 24 、C 25 、C 26 、C 27 、C 28 、C 29 and the like, specifically, pyridine, pyrimidine, pyrazine, pyridazine, triazine, furan, pyrrole, indene, indole, phenyl-indole, benzindole, phenyl-benzoindole, pyrazinoindole, quinoline, isoquinoline, benzoquinoline, pyridoquinoline, quinazoline, benzoquinazoline, dibenzoquinazoline, phenanthroquinazoline, quinoxaline, benzoquinoxaline, dibenzoquinoxaline, benzofuran, naphthobenzofuran, dibenzofuran, dinaphthofuran, thiophene, benzothiophene, dibenzothiophene, naphthobenzothiophene, dinaphthothiophene, carbazole, benz-carbazole, benzocarbazole, benz-benzocarbazole, naphthalene-benzocarbazole, dibenzocarbazole, benzofuropyridine, benzothienopyridine, benzofurano Pyrimidine, benzothienopyrimidine, benzothienopyrazine, benzofuropyrazine, benzimidazole, benzothiazole, benzoxazole, benzosilol, phenanthroline, dihydro-phenylphenazine, 10-phenyl-10H-phenoxazine, phenoxazine, phenothiazine, dibenzodioxine, benzodibenzodioxine, thianthrene, 9,9-dimethyl-9H-xanthene, 9,9-dimethyl-9H-thioxanthene, dihydrodimethylphenylacridine, spiro[fluorene-9,9'-xanthene], dibenzoselenophene, benzophosphindole, etc.

[0105] In the Ar 3 to Ar 5 、L 3 To L 5 When at least one of the groups is an aliphatic ring group, the aliphatic ring group may be, for example, C3 to C 30 、C3~C 29、C3~C 28 、C3~C 27 、C3~C 26 、C3~C 25 、C3~C 24 、C3~C 23 、C3~C 22 、C3~C 21 、C3~C 20 、C3~C 19 、C3~C 18 、C3~C 17 、C3~C 16 、C3~C 15 、C3~C 14 、C3~C 13 、C3~C 12 、C3~C 11 、C3~C 10 、C3~C8、C3~C6、C6、C 10 、C 11 、C 12 、C 13 、C 14 、C 15 、C 16 、C 17 、C 18 Specifically, an aliphatic ring group such as a cyclopentyl group, an indenyl group, a tetralinyl group, a cyclohexyl group, a norbornyl group, and an adamantyl group.

[0106] In the Ar 3 to Ar 5 At least one of them is a fluorenyl group or L 3 To L 5 When at least one of the fluorenyl groups is a fluorenyl group, the fluorenyl group or fluorenyl group may be 9,9-dimethyl-9H-fluorene, 9,9-diphenyl-9H-fluorene, 9,9'-spirobifluorene, spiro[benzo[b]fluorene-11,9'-fluorene], benzo[b]fluorene, 11,11-diphenyl-11H-benzo[b]fluorene, 9-(naphthalen-2-yl)9-phenyl-9H-fluorene, and the like.

[0107] In Chemical Formulas 1 to 3, Ar 3 to Ar 8 、Ar 20 、Ar 21 、L 3 To L 8 、L20 、L 21 、R 40 to R 43 Can be substituted by a substituent. For example, when Ar 3 to Ar 8 、Ar 20 、Ar 21 、L 3 To L 8 、L 20 、L 21 、R 40 to R 43 When at least one of the substituents is a substituent containing a hydrogen atom, the hydrogen atom may be further substituted by another substituent.

[0108] The Ar 3 to Ar 5 、Ar 20 、Ar 21 、L 3 To L 5 、L 20 、L 21 、R 40 to R 43 , can be selected from deuterium, halogen, C1~C 20 Alkyl or C6~C 20 Aryl substituted or unsubstituted silyl, C1~C 20 Alkyl or C6~C 20 Aryl substituted or unsubstituted phosphine oxide, siloxane, cyano, nitro, C1~C 20 Alkylthio, C1~C 20 Alkoxy, C6~C 30 Aryloxy, C6~C 30 Arylthio, C1~C 20 Halogenated alkyl, C1~C 20 Alkyl, C2~C 20 Alkenyl, C2~C 20 Alkynyl, C6~C 30 Aryl, C6~C substituted by deuterium 30 an aryl group, a fluorenyl group, a C2-C 30 Heterocyclic groups, and C3~C 30 The aliphatic ring group is further substituted by one or more substituents selected from the group consisting of:

[0109] The Ar 6 to Ar 8 、L 6 To L 8 can be selected from deuterium, cyano, C6~C30 Aryl, and C6~C 30 The aryl group is further substituted by one or more substituents selected from the group consisting of the aryl group.

[0110] The Ar 3 to Ar 8 、Ar 20 、Ar 21 、L 3 To L 8 、L 20 、L 21 、R 40 to R 43 When at least one of the is further substituted by an aryl group, the aryl group may be, for example, C6 to C 30 、C6~C 29 、C6~C 28 、C6~C 27 、C6~C 26 、C6~C 25 、C6~C 24 、C6~C 23 、C6~C 22 、C6~C 21 、C6~C 20 、C6~C 19 、C6~C 18 、C6~C 17 、C6~C 16 、C6~C 15 、C6~C 14 、C6~C 13 、C6~C 12 、C6~C 11 、C6~C 10 , C6, C 10 、C 12 、C 13 、C 14 、C 15 、C 16 、C 17 、C 18 etc.

[0111] The Ar 3 to Ar 5 、L 3 To L 8 When at least one of the is further substituted by an aliphatic cyclic group, the aliphatic cyclic group may be, for example, C3 to C 30 、C3~C 29 、C3~C 28 、C3~C 27 、C3~C 26 、C3~C 25、C3~C 24 、C3~C 23 、C3~C 22 、C3~C 21 、C3~C 20 、C3~C 19 、C3~C 18 、C3~C 17 、C3~C 16 、C3~C 15 、C3~C 14 、C3~C 13 、C3~C 12 、C3~C 11 、C3~C 10 、C3~C8、C3~C6、C6、C 10 、C 11 、C 12 、C 13 、C 14 、C 15 、C 16 、C 17 、C 18 Aliphatic cyclic groups such as the above.

[0112] The Ar 3 to Ar 5 、L 3 To L 8 When at least one of the fluorenyl groups is further substituted by a fluorenyl group, the fluorenyl group may be 9,9-dimethyl-9H-fluorene, 9,9-diphenyl-9H-fluorene, 9,9'-spirobifluorene, spiro[benzo[b]fluorene-11,9'-fluorene], benzo[b]fluorene, 11,11-diphenyl-11H-benzo[b]fluorene, 9-(naphthalen-2-yl)9-phenyl-9H-fluorene, and the like.

[0113] The Ar 3 to Ar 5 、Ar 20 、Ar 21 、L 3 To L 5 、L 20 、L 21 、R 40 to R 43 When at least one of the is further substituted by a heterocyclic group, the heterocyclic group may be, for example, C2 to C 30 、C2~C 29 、C2~C 28 、C2~C 27 、C2~C 26 、C2~C 25 、C2~C 24 、C2~C 23 、C2~C22 、C2~C 21 、C2~C 20 、C2~C 19 、C2~C 18 、C2~C 17 、C2~C 16 、C2~C 15 、C2~C 14 、C2~C 13 、C2~C 12 、C2~C 11 、C2~C 10 , C2~C9, C2~C8, C2~C7, C2~C6, C2~C5, C2~C4, C2~C3, C2, C3, C4, C5, C6, C7, C8, C9, C 10 、C 11 、C 12 、C 13 、C 14 、C 15 、C 16 、C 17 、C 18 、C 19 、C 20 、C 21 、C 22 、C 23 、C 24 、C 25 、C 26 、C 27 、C 28 、C 29 etc.

[0114] The Ar 3 to Ar 5 、L 3 To L 8 When at least one of the is further substituted by an alkyl group, the alkyl group may be, for example, C1 to C 20 、C1~C 10 , C1~C4, C1, C2, C3, C4 and the like alkyl groups, for example, methyl, ethyl, tert-butyl and the like.

[0115] The Ar 3 to Ar 5 、L 3 To L 8 When at least one of the alkyl groups is further substituted with a halogenated alkyl group, the halogenated alkyl group may be C1 to C 20 、C1~C 10 , C1-C4, C1, C2, C3, C4 and the like halogenated alkyl groups, for example, trifluoromethyl group and the like.

[0116] In the chemical formula 1, L 3 To L 5 At least one of them may be a structure represented by the following Chemical Formula L-1 or Chemical Formula L-2, but is not limited thereto.

[0117] <Chemical Formula L-1> <Chemical Formula L-2>

[0118] In the chemical formulas L-1 and L-2, each symbol can be defined as follows.

[0119] R 5 and R 6 Independently selected from deuterium, halogen, C1-C 20 Alkyl or C6~C 20 Aryl substituted or unsubstituted silyl, C1~C 20 Alkyl or C6~C 20 Aryl substituted or unsubstituted phosphine oxide, siloxane, cyano, nitro, C1~C 20 Alkylthio, C1~C 20 Alkoxy, C6~C 30 Aryloxy, C6~C 30 Arylthio, C1~C 20 Halogenated alkyl, C1~C 20 Alkyl, C2~C 20 Alkenyl, C2~C 20 Alkynyl, C6~C 30 Aryl, C6~C substituted by deuterium 30 an aryl group, a fluorenyl group, a C2-C 30 Heterocyclic groups, and C3~C 17 The adjacent groups can be combined with each other to form a ring.

[0120] e is an integer from 0 to 4, f is an integer from 0 to 6, and when they are respectively integers of 2 or more, R 5 Respectively, R 6 Same or different respectively.

[0121] The chemical formula L-1 may be selected from the group consisting of the following chemical formulas L-1-1 to L-1-3.

[0122] <Chemical Formula L-1-1> <Chemical Formula L-1-2> <Chemical Formula L-1-3>

[0123] In the chemical formulas L-1-1 to L-1-3, R 5 and e are the same as defined in Chemical Formula L-1.

[0124] The chemical formula L-2 can be expressed as any one of the following chemical formulas L-2-1 to L-2-10.

[0125] <Chemical Formula L-2-1> <Chemical Formula L-2-2> <Chemical Formula L-2-3> <Chemical Formula L-2-4>

[0126] <Chemical Formula L-2-5> <Chemical Formula L-2-6> <Chemical Formula L-2-7>

[0127] <Chemical Formula L-2-8> <Chemical Formula L-2-9> <Chemical Formula L-2-10>

[0128] In the chemical formulas L-2-1 to L-2-10, R 6 and f are the same as defined in Chemical Formula L-2.

[0129] In the chemical formula 1, Ar 3 to Ar 5 At least one of the compounds may be selected from the group consisting of the following chemical formulae Ar-1 to Ar-12, but is not limited thereto.

[0130] <Chemical Formula Ar-1> <Chemical Formula Ar-2> <Chemical Formula Ar-3> <Chemical Formula Ar-4>

[0131] <Chemical Formula Ar-5> <Chemical Formula Ar-6> <Chemical Formula Ar-7> <Chemical Formula Ar-8>

[0132] <Chemical Formula Ar-9> <Chemical Formula Ar-10> <Chemical Formula Ar-11>

[0133] <Chemical formula Ar-12>

[0134] In the chemical formulae Ar-1 to Ar-12, each symbol can be defined as follows.

[0135] R 7 to R11 independently selected from hydrogen, deuterium, halogen, C1-C 20 Alkyl or C6~C 20 Aryl substituted or unsubstituted silyl, C1~C 20 Alkyl or C6~C 20 Aryl substituted or unsubstituted phosphine oxide, siloxane, cyano, nitro, C1~C 20 Alkylthio, C1~C 20 Alkoxy, C6~C 30 Aryloxy, C6~C 30 Arylthio, C1~C 20 Halogenated alkyl, C1~C 20 Alkyl, C2~C 20 Alkenyl, C2~C 20 Alkynyl, C6~C 30 Aryl, C6~C substituted by deuterium 30 an aryl group, a fluorenyl group, a C2 to C3 group containing at least one hetero atom selected from the group consisting of O, N, S, Si and P 30 Heterocyclic groups, and C3~C 30 The adjacent groups can be combined with each other to form a ring.

[0136] X is O or S.

[0137] g is an integer from 0 to 5, h is an integer from 0 to 7, i is an integer from 0 to 9, j is an integer from 0 to 4, k is an integer from 0 to 3, and when they are respectively integers of 2 or more, R 7 Respectively, R 8 Respectively, R 9 Respectively, R 10 Respectively, R 11 Same or different respectively.

[0138] In the chemical formula 2, L 6 To L 8 At least one of them may be a structure represented by the following Chemical Formula L-3 or Chemical Formula L-4.

[0139] <Chemical Formula L-3> <Chemical Formula L-4>

[0140] In the chemical formulas L-3 and L-4, each symbol can be defined as follows.

[0141] R 5' and R 6' Independently selected from hydrogen, deuterium, cyano, C6~C 30 Aryl, and C6~C30 The adjacent groups can be combined with each other to form an aromatic ring.

[0142] When the ring formed by the mutual bonding of adjacent groups is an aromatic ring, the aromatic ring may be, for example, C6 to C 20 、C6~C 18 、C6~C 16 、C6~C 14 、C6~C 13 、C6~C 12 、C6~C 10 , C6, C 10 、C 12 、C 14 、C 15 、C 16 、C 18 Specifically, it can form an aromatic ring group of benzene, naphthalene, anthracene, phenanthrene, pyrene, etc.

[0143] e1 is an integer from 0 to 4, f1 is an integer from 0 to 6, and when they are respectively integers of 2 or more, R 5' Respectively, R 6' Same or different respectively.

[0144] The chemical formula L-3 can be expressed as any one of the following chemical formulas L-3-1 to L-3-3.

[0145] <Chemical Formula L-3-1> <Chemical Formula L-3-2> <Chemical Formula L-3-3>

[0146] In the chemical formula L-3-1 to the chemical formula L-3-3, R 5' and e1 are the same as defined in Chemical Formula L-3.

[0147] The chemical formula L-4 may be selected from the group consisting of the following chemical formulas L-4-1 to L-4-10.

[0148] <Chemical Formula L-4-1> <Chemical Formula L-4-2> <Chemical Formula L-4-3> <Chemical Formula L-4-4>

[0149] <Chemical Formula L-4-5> <Chemical Formula L-4-6> <Chemical Formula L-4-7>

[0150] <Chemical Formula L-4-8> <Chemical Formula L-4-9> <Chemical Formula L-4-10>

[0151] In the chemical formulas L-4-1 to L-4-10, R 6' and f1 are the same as defined in Chemical Formula L-4.

[0152] In the chemical formula 2, Ar 6 to Ar 8 At least one of the compounds may be selected from the group consisting of the following chemical formulae Ar-13 to Ar-20, but is not limited thereto.

[0153] <Chemical Formula Ar-13> <Chemical Formula Ar-14> <Chemical Formula Ar-15> <Chemical Formula Ar-16>

[0154] <Chemical Formula Ar-17> <Chemical Formula Ar-18> <Chemical Formula Ar-19> <Chemical Formula Ar-20>

[0155] In the chemical formulae Ar-13 to Ar-20, each symbol can be defined as follows.

[0156] R 7' to R 9' Independently selected from hydrogen, deuterium, cyano, C6~C 30 Aryl, and C6~C 30 The adjacent groups can be combined with each other to form an aromatic ring.

[0157] When the ring formed by the mutual bonding of adjacent groups is an aromatic ring, the aromatic ring may be, for example, C6 to C 20 、C6~C 18 、C6~C 16 、C6~C 14 、C6~C 13 、C6~C 12 、C6~C 10 , C6, C 10 、C 12 、C 14 、C 15 、C 16 、C 18 Specifically, it can form an aromatic ring group of benzene, naphthalene, anthracene, phenanthrene, pyrene, etc.

[0158] g1 is an integer from 0 to 5, h1 is an integer from 0 to 7, i1 is an integer from 0 to 9, j1 is an integer from 0 to 4, k1 is an integer from 0 to 3, and when they are respectively integers of 2 or more, R 7’ Respectively, R 8’ Respectively, R 9’ Same or different respectively.

[0159] The Chemical Formula 3 may be expressed as any one of the following Chemical Formulas 3-1 to 3-6.

[0160] <Chemical Formula 3-1> <Chemical Formula 3-2>

[0161] <Chemical Formula 3-3> <Chemical Formula 3-4>

[0162] <Chemical Formula 3-5> <Chemical Formula 3-6>

[0163] In the chemical formulas 3-1 to 3-6, Ar 20 、Ar 21 、L 20 、L 21 、R 40 、R 41 、R 42 、R 43 , c1, c2, c3 and c4 are the same as defined in Chemical Formula 3.

[0164] Specifically, the compound represented by Chemical Formula 1 may be one of the following compounds P2-1 to P2-104 and compounds P3-1 to P3-92, and the compound represented by Chemical Formula 2 may be one of compounds P3-1 to P3-92, but is not limited thereto.

[0165] 。

[0166] Specifically, the compound represented by Chemical Formula 3 may be one of the following compounds, but is not limited thereto.

[0167] .

[0168] The reorganization energy of the compound used as a host may affect the performance of the organic light-emitting device. The reorganization energy is described below.

[0169] Reorganization energy (RE) refers to the energy dissipated by changes in the molecular structure when charges (electrons and holes) migrate. It depends on molecular geometry, and the smaller the difference between the potential energy surface (PES) of the neutral state and the PES of the charged state, the smaller the reorganization energy value. The RE value can be calculated using the following formula.

[0170]

[0171] NONE: Neutral geometry of neutral molecules (= no opt.)

[0172] NOAE: Anion geometry of neutral molecules

[0173] NOCE: Cation geometry of neutral molecules

[0174] AONE: Neutral Geometry of Anion Molecules

[0175] AOAE: Anion geometry of anionic molecules (=AO opt.)

[0176] CONE: Neutral geometry of cation molecules

[0177] COCE: cationic geometry of cationic molecules (=CO optimization (CO opt.))

[0178] The reorganization energy value is inversely proportional to the charge mobility. Under the conditions of having the same r and T values, the RE value of each material directly affects the mobility.

[0179] The relationship between RE value and mobility is expressed as follows, explained using charge transfer matrix elements.

[0180]

[0181] λ :Reorganization energy

[0182] μ : Mobility

[0183] r: dimer displacement

[0184] t: intermolecular charge transfer matrix element

[0185] According to the above formula, the smaller the RE value is, the faster the charge mobility is.

[0186] To determine the reorganization energy, a simulation tool that can calculate potential energy based on molecular structure is required. For example, Gaussian09 (G09) and the Jaguar (JG) module of Schrödinger Materials Science can be used. Both G09 and JG analyze molecular properties through quantum mechanics (QM) calculations and offer functions for optimizing molecular structures and calculating the energy (single-point energy) associated with existing molecular structures.

[0187] Molecular QM calculations require significant computing resources. For example, two cluster servers can be used for these calculations. Each cluster server consists of four node workstations and one master workstation. Each node uses a central processing unit (CPU) with more than 36 cores to perform molecular QM calculations through symmetric multi-processing (SMP) parallel computing.

[0188] G09 calculates the reorganization energy using the optimized molecular structures and their potential energies in the neutral and charged states (NONE / COCE). By changing only the charge in the two optimized structures, the charge potential energy (NOCE) of the structure optimized for the neutral state and the neutral potential energy (CONE) of the structure optimized for the charge state are calculated. The reorganization energy is then calculated according to the following relationship.

[0189]

[0190] Since Schrödinger provides the function of automatically performing this calculation process, by only providing the molecular structure of the basic state (NO), the potential energy of each state can be calculated in turn through the JG module, and the RE value can be calculated.

[0191] Hereinafter, examples are given to specifically illustrate the synthesis examples of the compounds represented by Chemical Formulae 1 to 3 and the preparation examples of the organic electroluminescent device of the present invention, but the present invention is not limited to the following examples.

[0192] [Synthesis Example 1] Compound of Chemical Formula 1

[0193] The compound represented by Chemical Formula 1 according to the present invention (final product 2) can be synthesized as shown in Reaction Formula 1, but is not limited thereto.

[0194] <Reaction Formula 1>

[0195] 1. Synthesis Example of P2-1

[0196] Sub3-1 (13.5 g, 32.2 mmol) was dissolved in THF (Tetrahydrofuran) (161 mL), and Sub4-1 (10.0 g, 32.2 mmol), NaOH (3.9 g, 96.7 mmol), Pd(PPh3)4 (2.23 g, 1.93 mmol) and water (81 mL) were added in sequence and reacted at 80°C. After the reaction, C C The organic layer was extracted with MgS After drying and concentration, the concentrate was separated by silica gel column and then recrystallized to obtain 14.5 g (yield 79%) of the product.

[0197] 2. Synthesis Example of P2-19

[0198] Sub3-19 (10.0 g, 29.1 mmol) was dissolved in THF (145 mL), and Sub4-19 (10.0 g, 29.1 mmol), NaOH (3.5 g, 87.2 mmol), Pd(PPh3)4 (2.01 g, 1.74 mmol) and water (73 mL) were added. The product was synthesized according to the method of the synthesis example of P2-1 to obtain 11.6 g of the product (yield 76%).

[0199] 3. Synthesis Example of P2-68

[0200] Sub3-68 (11.0 g, 27.0 mmol) was dissolved in THF (135 mL), and Sub4-68 (10.0 g, 27.0 mmol), NaOH (3.2 g, 81.0 mmol), Pd(PPh3)4 (1.87 g, 1.62 mmol) and water (68 mL) were added. The product was synthesized according to the method of the synthesis example of P2-1 to obtain 12.8 g of the product (yield 77%).

[0201] 4. Synthesis Example of P2-72

[0202] Sub2-41 (6.4 g, 23.8 mmol) was dissolved in THF (119 mL), and Sub4-72 (10.0 g, 23.8 mmol), NaOH (2.9 g, 71.4 mmol), Pd(PPh3)4 (1.65 g, 1.43 mmol) and water (59 mL) were added. The product was synthesized according to the method of the synthesis example of P2-1 to obtain 9.0 g of the product (yield 72%).

[0203] 5. Synthesis Example of P2-97

[0204] Sub3-97 (13.5 g, 31.2 mmol) was dissolved in THF (156 mL), and Sub4-97 (10.0 g, 31.2 mmol), NaOH (3.7 g, 93.7 mmol), Pd(PPh3)4 (2.17 g, 1.87 mmol) and water (78 mL) were added. The product was synthesized according to the method of the synthesis example P2-1 to obtain 13.8 g of the product (yield 75%).

[0205] The FD-MS (Field Desorption-Mass Spectrometry) data of the compound of Chemical Formula 1 of the present invention prepared according to the above synthesis example are shown in Table 1 below.

[0206] [Table 1]

[0207] [Synthesis Example 2] Compound of Chemical Formula 2

[0208] The compound represented by Chemical Formula 2 according to the present invention (final product 2) can be synthesized as shown in Reaction Formula 2, but is not limited thereto.

[0209] <Reaction Formula 2>

[0210] 1. Synthesis Example of P3-1

[0211] Sub3-1 (5.0 g, 24.5 mmol) was dissolved in THF (Tetrahydrofuran) (123 mL), and Sub6-1 (10.3 g, 24.5 mmol), NaOH (2.9 g, 73.5 mmol), Pd(PPh3)4 (1.70 g, 1.47 mmol) and water (61 mL) were added in sequence and reacted at 80°C. After the reaction, C C The organic layer was extracted with MgS After drying and concentration, the concentrate was separated by silica gel column and recrystallized to obtain 10.1 g (yield 89%) of the product.

[0212] 2. Synthesis Example of P3-25

[0213] Sub3-19 (9.0 g, 26.3 mmol) was dissolved in THF (131 mL), and Sub6-25 (10.0 g, 26.3 mmol), NaOH (3.2 g, 78.9 mmol), Pd(PPh3)4 (1.82 g, 1.58 mmol) and water (66 mL) were added. The product was synthesized according to the method of the synthesis example of P3-1 to obtain 10.2 g of the product (yield 84%).

[0214] 3. Synthesis Example of P3-48

[0215] Sub5-48 (11.7 g, 29.8 mmol) was dissolved in THF (149 mL), and Sub6-48 (10.0 g, 29.8 mmol), NaOH (3.6 g, 89.5 mmol), Pd(PPh3)4 (2.07 g, 1.79 mmol) and water (75 mL) were added. The product was synthesized according to the method of the synthesis example of P3-1 to obtain 13.4 g of the product (yield 79%).

[0216] 4. Synthesis Example of P3-75

[0217] Sub5-75 (9.7 g, 24.6 mmol) was dissolved in THF (123 mL), and Sub6-75 (10.0 g, 24.6 mmol), NaOH (3.0 g, 73.8 mmol), Pd(PPh3)4 (1.71 g, 1.48 mmol) and water (62 mL) were added. The product was synthesized according to the method of the synthesis example of P3-1 to obtain 12.9 g of the product (yield 82%).

[0218] 5. Synthesis Example of P3-91

[0219] Sub5-91 (7.4 g, 23.2 mmol) was dissolved in THF (116 mL), and Sub6-91 (10.0 g, 23.2 mmol), NaOH (2.8 g, 69.7 mmol), Pd(PPh3)4 (1.61 g, 1.39 mmol) and water (58 mL) were added. The product was synthesized according to the method of the synthesis example of P3-1 to obtain 11.6 g of the product (yield 85%).

[0220] The FD-MS (Field Desorption-Mass Spectrometry) data of the compound of Chemical Formula 2 of the present invention prepared according to the above synthesis example are shown in Table 2 below.

[0221] [Table 2]

[0222] [Synthesis Example 3] Compound of Chemical Formula 3

[0223] The compound represented by Chemical Formula 3 according to the present invention (final product 5) can be synthesized as shown in Reaction Formula 3, but is not limited thereto.

[0224] <Reaction formula 3>

[0225] 1. Synthesis Example of P5-1

[0226] Sub9-1 (10.0 g, 24.5 mmol) was dissolved in toluene (122 mL), and Sub10-1 (3.8 g, 24.5 mmol), Pd2(dba)3 (0.67 g, 0.73 mmol), P(t-Bu)3 (0.30 g, 1.47 mmol), and NaOt-Bu (4.7 g, 49.0 mmol) were added in sequence and reacted at 80°C. After the reaction, C C The organic layer was extracted with MgS After drying and concentration, the concentrate was separated by silica gel column and recrystallized to obtain 10.1 g (yield 85%) of the product.

[0227] 2. Synthesis Example of P5-16

[0228] Sub9-16 (10.0 g, 20.1 mmol) was dissolved in toluene (100 mL), and Sub10-1 (3.1 g, 20.1 mmol), Pd2(dba)3 (0.55 g, 0.60 mmol), P(t-Bu)3 (0.24 g, 1.20 mmol), and NaOt-Bu (3.9 g, 40.1 mmol) were added. The product was synthesized according to the method of the synthesis example of P5-1 to obtain 9.5 g of the product (yield 82%).

[0229] 3. Synthesis Example of P5-23

[0230] Sub9-23 (10.0 g, 24.5 mmol) was dissolved in toluene (122 mL), and Sub10-23 (8.0 g, 24.5 mmol), Pd2(dba)3 (0.67 g, 0.73 mmol), P(t-Bu)3 (0.30 g, 1.47 mmol), and NaOt-Bu (4.7 g, 49.0 mmol) were added. The product was synthesized according to the method of the synthesis example of P5-1 to obtain 12.2 g of the product (yield 76%).

[0231] 4. Synthesis Example of P5-42

[0232] Sub9-42 (10.0 g, 21.8 mmol) was dissolved in toluene (109 mL), and Sub10-42 (5.1 g, 21.8 mmol), Pd2(dba)3 (0.60 g, 0.65 mmol), P(t-Bu)3 (0.26 g, 1.31 mmol), and NaOt-Bu (4.2 g, 43.6 mmol) were added. The product was synthesized according to the method of the synthesis example of P5-1 to obtain 11.2 g of the product (yield 84%).

[0233] 5. Synthesis Example of P5-48

[0234] Sub9-48 (10.0 g, mmol) was dissolved in toluene (122 mL), and Sub10-48 (7.1 g, 24.5 mmol), Pd2(dba)3 (0.67 g, 0.73 mmol), P(t-Bu)3 (0.30 g, 1.47 mmol), and NaOt-Bu (4.7 g, 49.0 mmol) were added. The product was synthesized according to the method of the synthesis example of P5-1 to obtain 11.7 g of the product (yield 72%).

[0235] The FD-MS (Field Desorption-Mass Spectrometry) data of the compound of Chemical Formula 3 of the present invention prepared according to the above synthesis example are shown in Table 3 below.

[0236] [Table 3]

[0237] Manufacturing and evaluation of organic electroluminescent devices

[0238] [Example 1] Green organic electroluminescent element (phosphorescent host)

[0239] A hole injection layer with a thickness of 70 nm was formed on the ITO layer (anode) by vacuum evaporation. 1 -(2-naphthyl)-N 4 ,N 4 -bis(4-(2-naphthyl(phenyl)amino)phenyl)-N 1 The hole-injection layer was then formed by vacuum-depositing N,N'-bis(1-naphthyl)-N,N'-bisphenyl-[1,1'-biphenyl]-4,4'-diamine (hereinafter referred to as "NPB") to a thickness of 70 nm on the hole-transport layer.

[0240] Next, tris(4-(9H-carbazol-9-yl)phenyl)amine (hereinafter referred to as “TCTA”) was vacuum-evaporated on the hole transport layer to a thickness of 30 nm, thereby forming a light-emitting auxiliary layer.

[0241] Subsequently, on the light-emitting auxiliary layer, a mixture of the compounds P2-32 (first host), P3-25 (second host) and P5-1 (third host) of the present invention in a mass ratio of 5:2:3 was used as the host material, and tris(2-phenylpyridyl)iridium (hereinafter referred to as "Ir(ppy)3") was used as a dopant to make the mass ratio of the host to the dopant 95:5, and a light-emitting layer with a thickness of 30 nm was formed by doping.

[0242] Next, (1,1'-biphenyl-4-ol)bis(2-methyl-8-quinolinol)aluminum (hereinafter referred to as BAlq) was deposited on the light-emitting layer by vacuum evaporation to form a hole blocking layer with a thickness of 10 nm. Subsequently, bis(10-hydroxybenzo[h]quinolinol)beryllium (hereinafter referred to as BeB) was vacuum deposited on the hole blocking layer with a thickness of 60 nm. ) to form an electron transport layer.

[0243] Then, LiF was deposited on the electron transport layer to a thickness of 0.2 nm to form an electron injection layer, and then Al was deposited to a thickness of 150 nm to form a cathode.

[0244] [Example 2] to [Example 48], [Comparative Example 1], [Comparative Example 2]

[0245] The organic electroluminescent element was prepared according to the method of Example 1, except that the mixture of the first host, the second host and the third host listed in Table 4 was used as the host material.

[0246] <Comparative Compound A>

[0247] A forward bias DC voltage was applied to the organic electroluminescent elements prepared in the examples and comparative examples of the present invention, and the electroluminescent (EL) characteristics were measured using a PR-650 from a photo research company in the United States. 2 The T95 lifespan of the reference luminance was measured using a lifespan measurement device manufactured by MC Science Co., Ltd. The measurement results are shown in Table 4 below.

[0248] [Table 4]

[0249] As shown in Table 4, compared to using Comparative Compound A (Comparative Example 1) or the compound represented by Chemical Formula 1 as the second host (Comparative Example 2), using a mixture of the compounds represented by Chemical Formulas 1 to 3 of the present invention as the host for the light-emitting layer (Examples 1 to 48) reduces the driving voltage of the organic electroluminescent device and significantly improves its efficiency and lifetime. Comparative Compound A used in Comparative Example 1 is an indolocarbazole-type substituted triazine compound, while Compound P2-70 used in Comparative Example 2 is a dibenzofuran-substituted triazine compound included in Chemical Formula 1 of the present invention. In contrast, the second host used in the examples of the present invention, represented by Chemical Formula 2, is a triazine compound composed solely of unsubstituted heterocyclic aryl groups.

[0250] In the case of a mixed host, the properties of the organic electroluminescent device vary depending on the substance used as the second host. Therefore, the type of substituent in the triazine compound as the second host affects the performance of the device.

[0251] Since the reorganization energy (RE) value varies depending on the substituent, the reorganization energy value of each compound was observed to observe the effect of reorganization energy on the characteristics of the device. The following Table 6 shows the calculation of RE for these compounds. elec The value of .

[0252] [Table 5]

[0253] A closer look at Table 5 reveals that P3-27 exhibits a lower RE value than both Comparative Compound A and Comparative Compound P2-70. A lower RE value indicates improved charge injection and mobility, facilitating charge injection from the host to the dopant, maintaining a suitable hole-to-electron ratio, and ultimately improving overall device performance.

[0254] Therefore, when the compound of Chemical Formula 2 of the present invention, which is a triazine compound substituted with an aryl group, is used as the second host, compared to the case of using Comparative Compound A or Compound P2-70 of Chemical Formula 1, which is a triazine compound substituted with a heterocyclic group, electrons transferred from the electron transport region can be quickly injected into the host, so that the hole-to-electron ratio can be appropriately maintained, thereby improving the overall driving voltage, efficiency, and life of the device.

[0255] The above description is for illustrative purposes only. A person skilled in the art will be able to make various modifications without departing from the essential characteristics of the present invention. The scope of protection of the present invention should be interpreted in accordance with the scope of protection claimed in the invention, and all technologies within the scope of equivalents thereof should be interpreted as included within the scope of the present invention.

Claims

1. An organic electroluminescent element comprising a first electrode, a second electrode, and an organic layer located between the first electrode and the second electrode, wherein: The organic layer includes a light-emitting layer, and the light-emitting layer includes a compound represented by the following chemical formula 1, a compound represented by the following chemical formula 2, and a compound represented by the following chemical formula 3: <Chemical Formula 1> <Chemical Formula 2> <Chemical Formula 3> In the Chemical Formulas 1 to 3, Ar 3 to Ar 5 Independently selected from C6~C 60 aryl; fluorenyl; C3~C 60 and containing at least one hetero atom selected from O, N, S, Si and P C2 ~ C 30 A group consisting of a heterocyclic group, L 3 To L 5 Independently selected from single bonds; C6~C 60 Arylene; Fluorenylene; C3~C 60 and containing at least one hetero atom selected from O, N, S, Si and P C2 ~ C 30 A group consisting of a heterocyclic group, Ar 6 to Ar 8 Independently of each other, C6~C 60 The aromatic group, L 6 To L 8 Independently selected from single bonds; or C6~C 60 arylene, a1 to a6 are independently integers from 0 to 3, Ar 20 and Ar 21 Independently selected from C6~C 60 aryl; fluorenyl; C3~C 60 and containing at least one hetero atom selected from O, N, S, Si and P C2 ~ C 60 A group consisting of a heterocyclic group, L 20 and L 21 Independently selected from single bonds; C6~C 60 Arylene; Fluorenylene; C3~C 60 and containing at least one hetero atom selected from O, N, S, Si and P C2 ~ C 60 A group consisting of a heterocyclic group, R 40 to R 43 independently selected from hydrogen; deuterium; halogen; cyano; nitro; C6~C 60 aryl; fluorenyl; C2~C containing at least one hetero atom selected from O, N, S, Si and P 60 Heterocyclic group; C3~C 60 Aliphatic ring group; C1~C 20 Alkyl; C2~C 20 Alkenyl; C2~C 20 Alkynyl; C1~C 20 Alkoxy; and C6~C 60 The adjacent groups can combine with each other to form a ring. c1 and c4 are integers from 0 to 4, c2 and c3 are integers from 0 to 3, The Ar 3 to Ar 5 、Ar 20 、Ar 21 、L 20 、L 21 、L 3 To L 5 、R 40 to R 43 , can be selected from deuterium, halogen, C1~C 20 Alkyl or C6~C 20 Aryl substituted or unsubstituted silyl, C1~C 20 Alkyl or C6~C 20 Aryl substituted or unsubstituted phosphine oxide, siloxane, cyano, nitro, C1~C 20 Alkylthio, C1~C 20 Alkoxy, C6~C 30 Aryloxy, C6~C 30 Arylthio, C1~C 20 Halogenated alkyl, C1~C 20 Alkyl, C2~C 20 Alkenyl, C2~C 20 Alkynyl, C6~C 30 Aryl, C6~C substituted by deuterium 30 Aryl, fluorenyl, C2-C12-C13-C16-C17-C18-C19-C19-C18 ...8-C18-C18-C18- 30 Heterocyclic groups, and C3~C 30 One or more substituents in the group consisting of an aliphatic ring group are further substituted, The Ar 6 to Ar 8 、L 6 To L 8 can be selected from deuterium, cyano, C6~C 30 Aryl, and C6~C 30 One or more substituents in the group consisting of aryl groups are further substituted, However, in the chemical formula 2, Ar is excluded. 3 to Ar 5 Contains at least one of the following substituents: and In the structure, the C ring, the D ring and the E ring are independently C6 to C 60 aromatic ring, V and W are independently O, S, N (R 11 ) or C (R 12 )(R 13 ), where R 11 to R 13 and are independently selected from hydrogen; deuterium; halogen; cyano; nitro; C6~C 60 aryl; fluorenyl; C2~C containing at least one hetero atom selected from O, N, S, Si and P 60 Heterocyclic group; C3~C 60 Aliphatic ring group; C1~C 20 Alkyl; C2~C 20 Alkenyl; C2~C 20 Alkynyl; C1~C 20 Alkoxy; and C6~C 60 A group composed of aryloxy groups.

2. The organic electroluminescent element according to claim 1, wherein The compound represented by Chemical Formula 1 is any one of the following compounds, 。 3. The organic electroluminescent element according to claim 1, wherein The compound represented by Chemical Formula 2 is any one of the following compounds: 。 4. The organic electroluminescent element according to claim 1, wherein The compound represented by Chemical Formula 3 is any one of the following compounds: 。 5. The organic electroluminescent device according to claim 1, wherein The organic electroluminescent element further includes a light efficiency improvement layer formed on a surface of the first electrode or the second electrode that is not in contact with the organic layer. The organic electroluminescent element according to claim 1 , wherein: The organic layer includes a hole transport region and an electron transport region.

7. The organic electroluminescent element according to claim 6, wherein The organic layer includes two or more stacks, and the stacks include the hole transport region and the electron transport region.

8. The organic electroluminescent element according to claim 7, wherein The organic layer further includes a charge generation layer formed between the two or more stacks.

9. An electronic device, wherein: include: A display device comprising the organic electroluminescent element according to claim 1; as well as A control unit is used to drive the display device.

10. The electronic device according to claim 9, wherein: The organic electroluminescent element is selected from the group consisting of an organic electroluminescent element, an organic transistor, an element for monochromatic lighting, and an element for quantum dot display.

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