Compound for organic electronic element, organic electronic element using the compound, and electronic device thereof

Abstract

The present invention provides a new compound capable of improving the luminous efficiency, stability, and service life of an element, an organic electronic element using the compound, and an electronic device thereof.

Description

Technical Field

[0001] The present invention relates to a compound for an organic electronic device, an organic electronic device using the compound, and an electronic device thereof. Background Art

[0002] Generally, the organic light emission phenomenon refers to the phenomenon of converting electrical energy into light energy by using an organic material. An organic electronic device using the organic light emission phenomenon generally has a structure including an anode, a cathode, and an organic material layer interposed therebetween. Here, in order to increase the efficiency and stability of the organic electronic device, the organic material layer is usually composed of a multilayer structure made of different materials, and may include, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like.

[0003] The materials used as the organic material layer in the organic electronic device can be classified into light emitting materials and charge transport materials according to their functions, such as hole injection materials, hole transport materials, electron transport materials, electron injection materials, and the like. And the light emitting materials can be classified into a high molecular weight type and a low molecular weight type according to the molecular weight, and can be classified into a fluorescent material derived from the singlet excited state of electrons and a phosphorescent material derived from the triplet excited state of electrons according to the light emission mechanism. In addition, the light emitting materials can be classified into a blue light emitting material, a green light emitting material, and a red light emitting material according to the emission color, and a yellow light emitting material and an orange light emitting material necessary for achieving a more natural color.

[0004] However, when only one material is used as the light emitting material, due to the intermolecular interaction, the maximum emission wavelength shifts to a longer wavelength, and there is a problem that the color purity is reduced or the device efficiency is reduced due to the emission attenuation effect. Therefore, in order to increase the color purity and the light emission efficiency by energy transfer, a host / dopant system can be used as the light emitting material. The principle is that when a small amount of dopant having a smaller band gap than that of the host forming the light emitting layer is mixed in the light emitting layer, the excitons generated in the light emitting layer are transferred to the dopant to emit light efficiently. At this time, since the wavelength of the host shifts to the wavelength band of the dopant, light having a desired wavelength can be obtained according to the type of the dopant used.

[0005] Currently, the portable display market is for large area displays, and their sizes are increasing day by day. Therefore, more power consumption is required than that required for existing portable displays. Therefore, for a portable display with a limited power source (such as a battery), power consumption has become a very important factor, and the problems of efficiency and service life must also be solved.

[0006] Efficiency, service life, and driving voltage are interrelated. When the efficiency increases, the driving voltage decreases relatively. As the driving voltage decreases, the crystallization of the organic material due to Joule heating generated during driving decreases, and thus the service life tends to increase. However, the efficiency cannot be simply maximized by improving the organic material layer. This is because long service life and high efficiency can be achieved simultaneously when the energy levels and T1 values between the organic material layers and the inherent properties of the materials (mobility, interface properties, etc.) are optimally combined.

[0007] Therefore, although the penetration and diffusion of metal oxides from the anode electrode (ITO) into the organic layer are delayed (which is one of the reasons for shortening the service life of organic electronic components), it should have stable properties to resist Joule heating generated during device driving. And OLED devices are mainly formed by deposition methods, and it is necessary to develop a material that can withstand long-term deposition, that is, a material with strong heat resistance.

[0008] In other words, in order to fully exhibit the excellent characteristics of organic electronic components, materials that can be stably and effectively used to form the organic material layer in the device, such as hole injection materials, hole transport materials, light-emitting materials, electron transport materials, electron injection materials, etc., should be given priority. However, stable and effective organic material layers for organic electronic devices have not been fully developed. Therefore, it is necessary to continuously develop new materials, and in particular, it is urgently necessary to develop host materials for the light-emitting layer. Summary of the Invention

[0009] To solve the problems in the above background technology, the present invention discloses a compound with a new structure, and when this compound is applied to organic electronic components, it has been found that the light-emitting efficiency, stability, and service life of the device can be significantly improved.

[0010] Therefore, the object of the present invention is to provide a new compound, an organic electronic component using the compound, and an electronic device thereof.

[0011] Technical Solution

[0012] The present invention provides a compound represented by formula (1).

[0013] Formula (1)

[0014]

[0015] On the other hand, the present invention provides an organic electronic component and an electronic device thereof that contain the compound represented by formula (1).

[0016] Advantages of the Invention

[0017] By using the compounds according to the present invention, high luminous efficiency, low driving voltage, and high heat resistance of the device can be achieved, and the color purity and service life of the device can be greatly improved. BRIEF DESCRIPTION OF THE DRAWINGS

[0018] Figures 1 to 3 is an exemplary view of an organic electroluminescent device according to the present invention. DETAILED DESCRIPTION

[0019] Hereinafter, some embodiments of the present invention will be described in detail. In addition, in the following description of the present invention, when the detailed description of known functions and configurations incorporated herein may make the subject matter of the present invention rather unclear, the detailed description will be omitted.

[0020] In addition, when describing components of the present invention, terms such as first, second, A, B, (a), (b), etc. may be used herein. Each of these terms is not used to define the essence, order, or sequence of the corresponding components, but is only used to distinguish the corresponding components from other components. It should be noted that if a component is described as "connected", "coupled", or "joined" to another component, the component can be directly connected or joined to the other component, but another component can be "connected", "coupled", or "joined" between the components.

[0021] As used in the specification and the appended claims, unless otherwise specified, the following are the meanings of the following terms.

[0022] Unless otherwise specified, the term "halo" or "halogen" as used herein includes fluorine, bromine, chlorine, or iodine.

[0023] Unless otherwise specified, the term "alkyl" or "alkyl group" as used herein has a single bond and has 1 to 60 carbon atoms, and means a saturated aliphatic functional group, including a straight-chain alkyl group, a branched-chain alkyl group, a cycloalkyl group (alicyclic), a cycloalkyl group substituted with an alkyl group, or an alkyl group substituted with a cycloalkyl group.

[0024] Unless otherwise specified, the term "alkenyl" or "alkynyl" as used herein has a double bond or a triple bond and has 2 to 60 carbon atoms, but is not limited thereto, and includes straight-chain or branched-chain groups.

[0025] Unless otherwise specified, the term "cycloalkyl" means an alkyl group forming a ring having 3 to 60 carbon atoms, but is not limited thereto.

[0026] Unless otherwise specified, the term "alkoxy group", "alkoxy", or "alkyloxy group" as used herein means an oxy group connected to an alkyl group having 1 to 60 carbon atoms, but is not limited thereto.

[0027] Unless otherwise indicated, the term "aryloxy group" or "aroxy group" as used herein means an oxy group attached to an aryl group having 6 to 60 carbon atoms, but is not limited thereto.

[0028] Unless otherwise indicated, the terms "aryl group" and "arylene group" used in the present invention each have 6 to 60 carbon atoms, but are not limited thereto. In the present invention, an aryl group or an arylene group means a monocyclic or polycyclic aromatic, and includes an aromatic ring formed by adjacent substituents that are linked or participate in a reaction.

[0029] For example, an aryl group may be phenyl, biphenyl, fluorenyl or spirofluorenyl.

[0030] The prefix "aryl" or "ar" means a group substituted with an aryl group. For example, arylalkyl may be an alkyl group substituted with an aryl group, and arylalkenyl may be an alkenyl group substituted with an aryl group, and the group substituted with an aryl group has the number of carbon atoms as defined herein.

[0031] In addition, when the prefixes are named in sequence, this means that the substituents are listed in the order first described. For example, arylalkoxy means an alkoxy group substituted with an aryl group, alkoxycarbonyl means a carbonyl group substituted with an alkoxy group, and arylcarbonylalkenyl also means an alkenyl group substituted with an arylcarbonyl group, where arylcarbonyl may be a carbonyl group substituted with an aryl group.

[0032] Unless otherwise indicated, the term "heterocyclic group" as used herein contains one or more heteroatoms, but is not limited thereto, has 2 to 60 carbon atoms, includes either a monocyclic or polycyclic ring, and may include a heteroaliphatic ring and a heteroaromatic ring. In addition, it may also combine with adjacent groups to form a heterocyclic group.

[0033] Unless otherwise indicated, the term "heteroatom" as used herein means at least one of N, O, S, P or Si.

[0034] In addition, the term "heterocyclic group" may include a ring in which carbon constituting the ring is replaced by SO 2 For example, the "heterocyclic group" includes the following compounds.

[0035]

[0036] Unless otherwise indicated, the term "fluorenyl group" or "fluorenylene group" as used herein refers to a monovalent or divalent functional group in which R, R' and R" are all hydrogen in the following structure, and the term "substituted fluorenyl group" or "substituted fluorenylene group" means that at least one of the substituents R, R', R" is a substituent other than hydrogen, and includes those in which R and R' are bonded to each other to form a spiro compound together with the carbon to which they are bonded.

[0037]

[0038] As used herein, the term "spiro compound" has "spiro linkage", and spiro linkage means a linkage in which two rings share only one atom. At this time, the atom shared in the two rings is called a "spiro atom", and these compounds are respectively called "monospiro-", "dispiro-", and "trispiro-" according to the number of spiro atoms in the compound.

[0039] Unless otherwise specified, the term "aliphatic" as used herein means an aliphatic hydrocarbon having 1 to 60 carbon atoms, and the term "aliphatic ring" as used herein means an aliphatic hydrocarbon ring having 3 to 60 carbon atoms.

[0040] Unless otherwise specified, the term "ring" as used herein means an aliphatic ring having 3 to 60 carbon atoms, or an aromatic ring having 6 to 60 carbon atoms, or a heterocyclic ring having 2 to 60 carbon atoms, or a fused ring formed by their combination, and includes a saturated ring or an unsaturated ring.

[0041] Other heterocompounds or heterogroups other than the above-mentioned heterocompounds include, but are not limited to, one or more heteroatoms.

[0042] In addition, unless otherwise specified, "substituted" in the term "substituted or unsubstituted" as used herein means substituted by one or more substituents selected from deuterium, halogen, amino group, nitrile group, nitro group, C 1 -C 20 alkyl group, C 1 -C 20 alkoxy group, C 1 -C 20 alkylamine group, C 1 -C 20 alkylthiophene group, C 6 -C 20 arylthiophene group, C 2 -C 20 alkenyl group, C 2 -C 20 alkynyl group, C 3 -C 20 cycloalkyl group, C 6 -C 20 aryl group, deuterium-substituted C 6 -C 20 aryl group, C 8 -C 20 arylalkenyl group, silyl group, boron group, germanium group and C 2 -C 20Heterocyclic groups, but not limited to these substituents.

[0043] In addition, unless otherwise explicitly explained, the definitions of the substituents defined by the formula used in the present invention are the same as those of the following formula.

[0044]

[0045] Here, when a is an integer of zero, the substituent R 1 does not exist. When a is an integer of 1, the only substituent R 1 is attached to any one of the carbons constituting the benzene ring. When a is an integer of 2 or 3, they are combined as follows, where R 1 can be the same as or different from each other. When a is an integer from 4 to 6, they are bonded to the carbons of the benzene ring in a similar manner, but the indication of the hydrogen bonded to the carbon forming the benzene ring is omitted.

[0046]

[0047] Hereinafter, compounds according to aspects of the present invention and organic electronic elements containing the compounds will be described.

[0048] The present invention provides a compound represented by formula (1).

[0049] Formula (1)

[0050]

[0051] Wherein,

[0052] 1) Ar 1 and Ar 2 are each independently a C 6 -C 18 aryl group; or a C 6 -C 18 aryl group substituted with deuterium;

[0053] 2) R 1 、R 2 、R 3 、R 4 、R 5 and R 6 are the same as or different from each other and are each independently hydrogen or deuterium;

[0054] 3) a is an integer from 0 to 7, and b is an integer from 0 to 6.

[0055] In addition, the present invention provides a compound in which formula (1) is represented by formula (1-1) or formula (1-2).

[0056]

[0057] Among them,

[0058] Ar 1 and Ar 2 , R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , a and b are the same as defined above.

[0059] In addition, the present invention provides a compound in which Ar 1 or Ar 2 is represented by any one of the following compounds.

[0060]

[0061] Among them,

[0062] 1) R 1 , R 2 and a are the same as defined above,

[0063] 2) a' and b' are independently integers from 0 to 5, and a" is an integer from 0 to 4,

[0064] 3) * indicates the bonding position.

[0065] In addition, the present invention provides a compound in which the reorganization energy value of the compound represented by formula (1) is less than 0.190.

[0066] In addition, the present invention provides a compound in which the reorganization energy value of the compound represented by formula (1) is 0.155 to 0.170.

[0067] In addition, the present invention provides a compound in which the compound represented by formula (1) is represented by any one of the following compounds P-1 to P-64.

[0068]

[0069]

[0070]

[0071]

[0072]

[0073] Reference Figure 1, the organic electronic device (100) according to the present invention includes a first electrode (110), a second electrode (170), and an organic material layer between the first electrode (110) and the second electrode (170) including a single compound represented by Formula (1) or two or more compounds. In this case, 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.

[0074] The organic material layer may sequentially 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) on the first electrode (110). In this case, the remaining layers except for the light-emitting layer (140) may not be formed. It may also include a hole blocking layer, an electron blocking layer, a light-emitting auxiliary layer (220), a buffer layer (210), etc., and the electron transport layer (150), etc. may be used as a hole blocking layer. (See Figure 2 )

[0075] In addition, the organic electronic device according to an embodiment of the present invention may further include a protective layer or a light efficiency enhancing layer (180). The light efficiency enhancing layer may be formed on one surface of the two surfaces of the first electrode that does not contact the organic material layer, or formed on one surface of the two surfaces of the second electrode that does not contact the organic material layer. The compound according to an embodiment of the present invention applicable to the organic material layer may be used as a host or a dopant of the hole injection layer (120), the hole transport layer (130), the light-emitting auxiliary layer (220), the electron transport auxiliary layer, the electron transport layer (150), and the electron injection layer (160), the light-emitting layer (140), or as a material of the light efficiency enhancing layer. Preferably, for example, the compound according to Formula (1) of the present invention may be used as a host material of the light-emitting layer, the hole blocking layer, or the electron transport layer.

[0076] The organic material layer may include two or more stacked bodies, including a hole transport layer, a light-emitting layer, and an electron transport layer sequentially formed on the anode, and further includes a charge generation layer formed between the two or more stacked bodies (see Figure 3 ).

[0077] In addition, even in the case of the same nucleus, the band gap, electrical properties, interface properties, etc. may vary depending on the position where the substituent is bonded. Therefore, the selection of the combination of the nucleus and the sub-substituents bonded thereto is also very important. In particular, when achieving an optimal combination of the energy levels and T1 values of each organic material layer and the unique properties of the material (mobility, interface properties, etc.), long service life and high efficiency can be achieved simultaneously.

[0078] An organic electroluminescent device according to an embodiment of the present invention can be manufactured using a PVD (Physical Vapor Deposition) method. For example, a conductive metal, metal oxide, or alloy thereof is deposited on a substrate to form an anode, and after forming an organic material 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) thereon, it can be prepared by depositing a material that can be used as a cathode thereon.

[0079] In addition, in the present invention, the organic material layer is formed by any one of a spin coating process, a nozzle printing process, an inkjet printing process, a slot coating process, a dip coating process, and a roll-to-roll process, and the organic material layer provides an organic electronic element containing the compound as an electron transport material.

[0080] As another specific example, the same or different compounds represented by formula (1) are mixed and used in the organic material layer.

[0081] In addition, the present invention provides a light-emitting layer composition containing the compound represented by formula (1), and provides an organic electronic element including the light-emitting layer.

[0082] In addition, the present invention provides a hole blocking layer composition containing the compound represented by formula (1), and provides an organic electronic element including the hole blocking layer.

[0083] In addition, the present invention provides an electron transport layer composition containing the compound represented by formula (1), and provides an organic electronic element including the electron transport layer.

[0084] In addition, the present invention provides an electronic device including a display device including an organic electronic element; and a control unit for driving the display device.

[0085] On the other hand, the organic electronic element is at least one of an organic electroluminescent device, an organic solar cell, an organic photoreceptor, an organic transistor, and a device for monochromatic or white illumination. At this time, the electronic device can be a current or future wired / wireless communication terminal, and covers all kinds of electronic devices, including mobile communication terminals such as mobile phones, personal digital assistants (PDAs), electronic dictionaries, point-to-multipoint (PMPs), remote controls, navigation units, game consoles, various TVs, and various computers.

[0086] Hereinafter, a synthesis example of the compound represented by formula (1) of the present invention and a manufacturing example of the organic electronic element of the present invention will be described in detail with reference to examples, but the present invention is not limited to the following examples.

[0087] [Synthesis Example]

[0088] The compound (final product) represented by formula (1) according to the present invention is synthesized by reacting Sub 1 and Sub 2 as shown in Scheme 1 below, but is not limited thereto.

[0089] <Reaction Scheme 1>

[0090]

[0091] I. Synthesis of Sub 1

[0092] Sub 1 in Reaction Scheme 1 can be synthesized by the reaction route of Reaction Scheme 2 below, but is not limited thereto.

[0093] <Reaction Scheme 2>

[0094]

[0095] Synthesis examples of specific compounds belonging to Sub 1 are as follows.

[0096] 1. Synthesis example of Sub 1-1

[0097]

[0098] (1) Synthesis of Sub 1-1b

[0099] Add naphthalene-2-ylboronic acid (23.9 g, 0.14 mol), Pd(PPh 3 ) 4 (6.1 g, 0.005 mol), NaOH (21 g, 0.52 mol), THF (350 mL) and water (115 mL) to Sub 1-1a (50 g, 0.17 mol), and react at 70 °C for 6 hours.

[0100] When the reaction is complete, cool the temperature of the reaction mixture to room temperature and remove the solvent. Then, separate and concentrate the reaction mixture using a silica gel column or recrystallization method to obtain 48 g (82.4%) of the product Sub 1-1b.

[0101] (2) Synthesis of Sub 1-1

[0102] Add Sub 1-1b (30 g, 0.09 mol), 1,3-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene (29.7 g, 0.09 mol), Pd(PPh 3 ) 4(3.1 g, 0.003 mol), NaOH (10.8 g, 0.27 mol), THF (180 mL) and water (60 mL), and the reaction was carried out at 70 °C for 6 hours. When the reaction was completed, the temperature of the reactants was cooled to room temperature, and the solvent was removed. Then, the concentrated reactants were separated using a silica gel column or recrystallization method to obtain 33 g (80.4%) of the product Sub 1-1.

[0103] 2. Synthesis Example of Sub 1-5

[0104]

[0105] (1) Synthesis of Sub 1-5b

[0106] Add (naphthalen-2-yl-d7)boronic acid (24.5 g, 0.14 mol), Pd(PPh 3 ) 4 (4.8 g, 0.004 mol), NaOH (16.4 g, 0.41 mol), THF (280 mL) and water (90 mL) to Sub 1-5a (40 g, 0.14 mol), and the reaction was carried out at 70 °C for 6 hours. When the reaction was completed, 35 g (73.8%) of the product Sub 1-5b was obtained by using the separation method of Sub 1-1b described above.

[0107] (2) Synthesis of Sub 1-5

[0108] Add Sub 1-5b (35 g, 0.10 mol), 1,3-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene (33.4 g, 0.10 mol), Pd(PPh 3 ) 4 (3.5 g, 0.003 mol), NaOH (12.1 g, 0.30 mol), THF (200 mL), water (70 mL), and the reaction was carried out at 70 °C for 6 hours. When the reaction was completed, the temperature of the reactants was cooled to room temperature, and the solvent was removed. When the reaction was completed, 35 g (73.8%) of the product Sub 1-5 was obtained by using the separation method for Sub 1-1 described above.

[0109] 3. Synthesis Example of Sub 1-7

[0110]

[0111] (1) Synthesis of Sub 1-1b

[0112] 48 g (82.4%) of the product Sub1-1b was obtained by using the synthesis method of Sub 1-1b described above.

[0113] (2) Synthesis of Sub 1-7

[0114] Add Sub 1-1b (30 g, 0.09 mol), 1,2-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene (29.7 g, 0.09 mol), Pd(PPh 3 ) 4 (3.1 g, 0.003 mol), NaOH (10.8 g, 0.27 mol), THF (180 mL) and water (60 mL), and react at 70 °C for 6 hours. When the reaction is complete, 35 g (85.2%) of the product Sub 1-7 is obtained by using the separation method for Sub 1-1 described above.

[0115] 4. Synthesis Example of Sub 1-9

[0116]

[0117] (1) Synthesis of Sub 1-9b

[0118] Add naphthalene-2-ylboronic acid (23.4 g, 0.14 mol), Pd(PPh 3 ) 4 (4.8 g, 0.004 mol), NaOH (16.4 g, 0.41 mol), THF (280 mL) and water (90 mL) to Sub 1-5a (40 g, 0.14 mol), and react at 70 °C for 6 hours. When the reaction is complete, 38 g (81.8%) of the product Sub 1-9b is obtained by using the separation method for Sub 1-1b described above.

[0119] (2) Synthesis of Sub 1-9

[0120] Add Sub 1-9b (38 g, 0.11 mol), 1,2-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene (37 g, 0.11 mol), Pd(PPh 3 ) 4 (3.9 g, 0.003 mol), NaOH (13.5 g, 0.34 mol), THF (230 mL) and water (70 mL), and react at 70 °C for 6 hours. When the reaction is complete, 42 g (81.1%) of the product Sub 1-9 is obtained by using the separation method for Sub 1-1 described above.

[0121] Meanwhile, the compounds belonging to Sub 1 can be the following compounds, but are not limited thereto, and Table 1 below shows the FD-MS (field desorption - mass spectrometry) values of the compounds belonging to Sub 1-1.

[0122]

[0123] [Table 1]

[0124]

[0125] Meanwhile, the compounds belonging to Sub 2 can be the following compounds, but are not limited thereto, and Table 2 below shows the field desorption - mass spectrometry (FD-MS) values of the compounds belonging to Sub 2.

[0126]

[0127] [Table 2]

[0128]

[0129]

[0130] II. Synthesis of the Final Product

[0131] 1. Synthesis Example of P-1

[0132]

[0133] Add Sub 1-1 (20 g, 0.04 mol), Sub 2-1 (11.7 g, 0.04 mol), Pd(PPh 3 ) 4 (1.5 g, 0.001 mol), NaOH (5.3 g, 0.13 mol), THF (90 mL) and water (30 mL), and react at 70 °C for 6 hours. When the reaction is complete, cool the temperature of the reaction mixture to room temperature and remove the reaction solvent. Then, separate and concentrate the reacted mixture using a silica gel column or recrystallization method to obtain 22 g (89.4%) of product P-1.

[0134] 2. Synthesis Example of P-3

[0135]

[0136] Add Sub 1-1 (20 g, 0.04 mol), Sub 2-3 (13.9 g, 0.04 mol), Pd(PPh 3 ) 4(1.5 g, 0.001 mol), NaOH (5.3 g, 0.13 mol), THF (90 mL) and water (30 mL), and the reaction was carried out at 70 °C for 6 hours. When the reaction was completed, 23 g (85.8%) of product P-3 was obtained by using the separation method of P-1 described above.

[0137] 3. Synthesis Example of P-10

[0138]

[0139] Add Sub 1-1 (33 g, 0.07 mol), Sub 2-28 (30.3 g, 0.07 mol), Pd(PPh 3 ) 4 (2.5 g, 0.002 mol), NaOH (8.7 g, 0.22 mol), THF (90 mL) and water (50 mL), and the reaction was carried out at 70 °C for 6 hours. When the reaction was completed, 46 g (89.1%) of product P-10 was obtained by using the separation method of P-1 described above.

[0140] 4. Synthesis Example of P-25

[0141]

[0142] Add Sub 1-2 (30 g, 0.06 mol), Sub 2-1 (17.3 g, 0.06 mol), Pd(PPh 3 ) 4 (2.2 g, 0.002 mol), NaOH (7.8 g, 0.19 mol), THF (130 mL) and water (40 mL), and the reaction was carried out at 70 °C for 6 hours. When the reaction was completed, 30 g (81.5%) of product P-25 was obtained by using the separation method of P-1 described above.

[0143] 5. Synthesis Example of P-29

[0144]

[0145] Add Sub 1-2 (35 g, 0.08 mol), Sub 2-14 (20.6 g, 0.08 mol), Pd(PPh 3 ) 4 (2.6 g, 0.002 mol), NaOH (9.1 g, 0.23 mol), THF (150 mL) and water (50 mL), and the reaction was carried out at 70 °C for 6 hours. When the reaction was completed, 40 g (92.3%) of product P-29 was obtained by using the separation method of P-1 described above.

[0146] 6. Synthesis Example of P-34

[0147]

[0148] Add Sub 1-7 (30 g, 0.07 mol), Sub 2-2 (20.9 g, 0.07 mol), Pd(PPh 3 ) 4 (2.3 g, 0.002 mol), NaOH (7.9 g, 0.20 mol), THF (130 mL) and water (40 mL), and react at 70 °C for 6 hours. When the reaction is completed, 32 g (79.6%) of the product P-34 is obtained by using the above separation method for P-1.

[0149] 7. Synthesis Example of P-51

[0150]

[0151] Add Sub 1-7 (20 g, 0.04 mol), Sub 2-12 (16.1 g, 0.04 mol), Pd(PPh 3 ) 4 (1.5 g, 0.001 mol), NaOH (5.3 g, 0.13 mol), THF (90 mL) and water (30 mL), and react at 70 °C for 6 hours. When the reaction is completed, 26 g (89.7%) of the product P-51 is obtained by using the above separation method for P-1.

[0152] 8. Synthesis Example of P-62

[0153]

[0154] Add Sub 1-9 (15 g, 0.03 mol), Sub 2-14 (8.8 g, 0.03 mol), Pd(PPh 3 ) 4 (1.1 g, 0.001 mol), NaOH (3.9 g, 0.10 mol), THF (65 mL) and water (20 mL), and react at 70 °C for 6 hours. When the reaction is completed, 15 g (80.8%) of the product P-62 is obtained by using the above separation method for P-1.

[0155] Meanwhile, the FD-MS values of the compounds P-1 to P-64 of the present invention prepared according to the above synthesis examples are shown in Table 3 below.

[0156] [Table 3]

[0157]

[0158]

[0159]

[0160] Reorganization energy (abbreviated as RE hereinafter) refers to the energy lost due to the change in the molecular structure arrangement when charges (electrons, holes) move. It depends on the molecular geometry and has the characteristic that its value decreases as the difference between the potential energy surface of the neutral state (abbreviated as PES hereinafter) and the PES of the charged state decreases. The RE value can be obtained by the following formula.

[0161] RE 空穴 : λ + =(E NOCE -E COCE )+(E CONE -E NONE )

[0162] RE 电子 : λ-=(E NOAE -E AOAE )+(E AONE -E NONE )

[0163] Each factor can be defined as follows.

[0164] -NONE: Neutral geometry of the neutral molecule (hereinafter, NO opt.)

[0165] -NOAE: Anionic geometry of the neutral molecule

[0166] -NOCE: Cationic geometry of the neutral molecule

[0167] -AONE: Neutral geometry of the anionic molecule

[0168] -AOAE: Anionic geometry of the anionic molecule (hereinafter, AO opt.)

[0169] -CONE: Neutral geometry of the cationic molecule

[0170] -COCE: Cationic geometry of the cationic molecule (hereinafter, CO opt.)

[0171] Reorganization energy and mobility are inversely proportional to each other, and under the condition that they have the same r and T values, the RE value directly affects the mobility of each material. The relationship between the RE value and the mobility is expressed as follows.

[0172]

[0173]

[0174] Each factor can be defined as follows.

[0175] -λ: Reorganization energy

[0176] -μ: Mobility

[0177] -r: Dimer displacement

[0178] -t: Intermolecular charge transfer matrix element

[0179] As can be seen from the above equation, the lower the RE value, the faster the mobility.

[0180] The RE value requires a simulation tool that can calculate the potential energy based on the molecular structure, and we use the Gaussian09 (hereinafter referred to as G09) and Jaguar (hereinafter referred to as JG) modules of Schrodinger Materials Science. Both G09 and JG are tools for analyzing molecular properties through quantum mechanics (hereinafter referred to as QM) calculations and have the function of optimizing the molecular structure or calculating the energy (single-point energy) of a given molecular structure.

[0181] The process of calculating QM in the molecular structure requires a large amount of computing resources, and we use two cluster servers to perform these calculations. Each cluster server consists of 4 node workstations and 1 master workstation, and each node performs molecular QM calculations through symmetric multiprocessing (SMP) parallel computing using a central processing unit (CPU) with 36 or more cores.

[0182] The optimized molecular structures and their potential energies (NONE / COCE) in the neutral / charged states required for calculating the reorganization energy using G09. The potential energy of the charged state (NOCE) of the structure optimized for the neutral state and the potential energy of the neutral state (CONE) of the structure optimized for the charged state are calculated by changing only the charge to two optimized structures. Then, the reorganization energy is calculated according to the following relationship.

[0183] RE 电荷 : λ = (E NOCE - E COCE ) + (E CONE - E NONE )

[0184] Since provides a function to automatically execute this calculation process, by providing the molecular structure (NO) of the ground state, the potential energy according to each state is calculated sequentially through the JG module, and the RE value is calculated.

[0185] Meanwhile, the RE values of the present invention calculated according to the above calculation method are shown in Table 4 below.

[0186] [Table 4]

[0187] Compound Recombinant Energy (RE) P-1 0.157 P-3 0.158 P-25 0.156 P-26 0.157

[0188] In addition, the RE values of the comparative compounds calculated according to the calculation method described above are shown in Table 5 below.

[0189] [Table 5]

[0190]

[0191]

[0192] [Example 1] Red Organic Light-Emitting Device (Phosphorescent Host)

[0193] The organic electroluminescent device was fabricated by a conventional method using the compound obtained by synthesis as the luminescent host material of the light-emitting layer. First, N1-(naphthalen-2-yl)-N4,N4-bis(4-(naphthalen-2-yl(phenyl)amino)phenyl)-N1-phenylbenzene-1,4-diamine (abbreviated as 2-TNATA) was vacuum-deposited on the ITO layer (anode) formed on a glass substrate to form a 60-nm-thick hole injection layer, and 4,4-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (hereinafter abbreviated as NPD) was vacuum-deposited as a hole-transporting compound on the hole injection layer to a thickness of 60 nm to form a hole-transporting layer.

[0194] As the host on the hole-transporting layer, the compound (P-1) of the present invention represented by formula (1) was used, and (piq) was doped as a dopant material at a weight ratio of 95:5 2 Ir(acac) [bis(1-phenylisoquinolinato)iridium(III) acetylacetonate] was deposited to form a 30-nm-thick light-emitting layer. Subsequently, (1,1'-biphenyl)-4-oleato)bis(2-methyl-8-quinolinolate)aluminum (abbreviated as BAlq) was vacuum-deposited to a thickness of 10 nm as a hole-blocking layer, and tris(8-hydroxyquinolinato)aluminum (abbreviated as Alq3) was deposited to a thickness of 40 nm as an electron-transporting layer. Then, LiF (alkali metal halide) was deposited to a thickness of 0.2 nm as an electron injection layer, and then Al was deposited to a thickness of 150 nm and used as the cathode to prepare the organic electroluminescent device.

[0195] [Example 2] to [Example 4]

[0196] An organic electroluminescent device was prepared in the same manner as in Example 1, except that the compound of the present invention shown in Table 6 was used instead of the compound of the present invention (P-1) as the host material of the light-emitting layer.

[0197] [Example 5]

[0198] An organic electroluminescent device was prepared in the same manner as in Example 1, except that the compound of the present invention (P-1) and the following compound DSNL1 were used as the host material of the light-emitting layer at a weight ratio of 5:5.

[0199] [Example 6] to [Example 24]

[0200] An organic electroluminescent device was prepared in the same manner as in Example 1, except that the compound of the present invention shown in Table 6 and the following compound DSNL1 or DSNL2 were used as the first compound as the host material of the light-emitting layer at a weight ratio of 5:5 instead of the compound of the present invention (P-1).

[0201]

[0202] [Comparative Example 1] to [Comparative Example 4]

[0203] An organic electroluminescent device was fabricated in the same manner as in Example 1, except that the following Comparative Compound A to Comparative Compound D were used as the host material of the light-emitting layer.

[0204]

[0205] [Comparative Example 5] to [Comparative Example 12]

[0206] An organic electroluminescent device was fabricated in the same manner as in Example 1, except that Comparative Compound A to Comparative Compound D and Compound DSNL1 or DSNL2 were used at a weight ratio of 5:5 as the host material of the light-emitting layer.

[0207] By applying a forward bias DC voltage to the organic electronic devices prepared in Examples 1 to 24 and Comparative Examples 1 to 12 prepared in this way, the electroluminescence (EL) characteristics were measured using a PR-650 from photo research, and as a measurement result, the T95 service life was measured using a service life measurement device manufactured by McScience at 2500 cd / m 2 Standard brightness was used to measure the T95 service life. Table 6 below shows the device manufacturing and evaluation results.

[0208] [Table 6]

[0209]

[0210]

[0211] As can be seen from the results in Table 6, when the compound of the present invention is used as a material for the light-emitting layer, it can be seen that the driving voltage is reduced and the efficiency and service life are significantly improved compared with the cases of using Comparative Compounds A to D.

[0212] It was found that when different types of compounds are used in combination, the overall device results are improved compared with when the light-emitting layer compound is used alone. This shows the same trend in the results of Comparative Compounds A to D and the device results of the present invention.

[0213] More specifically, the compound of the present invention has a lower RE value than the comparative compounds. It can be seen that the compound of the present invention has a lower RE value only when a plurality of naphthyl groups linked to a phenylene group are bonded to triazine and their bonding positions are the specific positions described in the present invention. In addition, when a substituent having an excessive number of carbon atoms in the substitution configuration is substituted, it is used as a factor for increasing the RE value.

[0214] Since the RE value is inversely proportional to the mobility, a low RE value means a high mobility, and this mobility means a fast EOD. In summary, it can be seen that the compound of the present invention having a fast EOD value has the characteristics of a fast driving voltage, high efficiency, and long service life.

[0215] Referring to the compounds of the present invention, it can be seen that the RE value has a value of 0.155 to 0.170, and as a common feature of these compounds, the driving voltage is pulled down and the efficiency is increased.

[0216] When the light-emitting layer is composed of a variety of mixtures, its characteristics vary depending on the types of the first compound and the second compound, and the device results of the compound of the present invention and the comparative compounds show the same trend. Finally, it can be seen that the driving voltage, efficiency, and service life are determined according to the injection characteristics of holes and electrons into the dopant. In the present invention, it can be seen that through the relationship between the RE value and the mobility, an overall driving voltage reduction effect, an efficiency and service life increase effect are brought about. In addition, the present invention is an invention in which three substituents are introduced into triazine, and when specific substituents are combined, it has a positive effect on the total mobility and acts in the ratio of holes to electrons (for example, energy balance, stability, etc.), showing an overall improved result.

[0217] Comparing the compounds of the examples, the RE value is determined according to the type of substituent substituted in the same skeleton, and the injection and migration characteristics of holes and electrons are changed according to different RE values. Therefore, the compounds of the examples show different properties from each other according to the type of substituent.

[0218] Although exemplary embodiments of the present invention have been described for illustrative purposes, those skilled in the art will understand that various modifications, additions, and substitutions are possible without departing from the scope and spirit of the present invention as disclosed in the appended claims. Therefore, the embodiments disclosed in the present invention are intended to illustrate the scope of the technical concept of the present invention, and the scope of the present invention is not limited by the embodiments. The scope of the present invention should be interpreted based on the appended claims and should be interpreted to include all technical concepts within the scope equivalent to the claims as belonging to the present invention.

[0219] Brief Description of the Drawings

[0220] 100, 200, 300: Organic electronic element; 110: First electrode

[0221] 120: Hole injection layer; 130: Hole transport layer

[0222] 140: Light-emitting layer; 150: Electron transport layer

[0223] 160: Electron injection layer; 170: Second electrode

[0224] 180: Light efficiency enhancement layer; 210: Buffer layer

[0225] 220: Light-emitting assist layer; 320: First hole injection layer

[0226] 330: First hole transport layer; 340: First light-emitting layer

[0227] 350: First electron transport layer; 360: First charge generation layer

[0228] 361: Second charge generation layer; 420: Second hole injection layer

[0229] 430: Second hole transport layer; 440: Second light-emitting layer

[0230] 450: Second electron transport layer; CGL: Charge generation layer

[0231] ST1: First stack; ST2: Second stack

Claims

1. A compound represented by formula (1): Formula (1) wherein 1) Ar 1 and Ar 2 each independently is a C 6 -C 18 aryl group; or a C 6 -C 18 aryl group substituted with deuterium; 2)R 1 、R 2 、R 3 、R 4 、R 5 and R 6 are the same as or different from one another and are each independently hydrogen or deuterium; 3) a is an integer from 0 to 7 and b is an integer from 0 to 6.

2. The compound according to claim 1, wherein the compound represented by formula (1) is represented by formula (1-1) or formula (1-2): wherein Ar 1 、 Ar 2 、 R 1 、 R 2 、 R 3 、 R 4 、 R 5 、 R 6 、 a and b are the same as those defined in claim 1.

3. The compound according to claim 1, wherein Ar 1 or Ar 2 is represented by any one of the following compounds: wherein 1)R 1 、R 2 and a are the same as defined in claim 1, 2) a' and b' are each independently an integer from 0 to 5, and a" is an integer from 0 to 4, 3) * represents the bonding position.

4. The compound according to claim 1, wherein the reorganization energy value is less than 0.

190.

5. The compound according to claim 1, wherein the reorganization energy value is from 0.155 to 0.

170.

6. The compound according to claim 1, wherein formula (1) is represented by any one of compounds P-1 to P-64 below:

7. An organic electronic device, comprising: a first electrode, a second electrode, and an organic material layer formed between the first electrode and the second electrode, wherein the organic material layer includes a light-emitting layer, a hole-blocking layer, and an electron-transporting layer, and wherein the light-emitting layer contains the compound represented by formula (1) according to claim 1.

8. The organic electronic device according to claim 7, wherein the light-emitting layer contains a first host compound and a second host compound; and wherein the first host compound or the second host compound includes the compound represented by formula (1).

9. The organic electronic device according to claim 7, further comprising a light efficiency enhancement layer formed on at least one surface of the first electrode and the second electrode opposite to the organic material layer.

10. The organic electronic device according to claim 7, wherein the organic material layer includes at least two or more stacked bodies, and each stacked body includes a hole-transporting layer, a light-emitting layer, and an electron-transporting layer formed in sequence on the first electrode.

11. The organic electronic device according to claim 10, wherein the organic material layer further includes a charge generation layer formed between the two or more stacked bodies.

12. An electronic device, comprising: a display device including the organic electronic device according to claim 7; and a control unit for driving the display device.

13. The electronic device according to claim 12, wherein the organic electronic device is any one of an organic electroluminescent device, an organic solar cell, an organic photoreceptor, an organic transistor, and a device for monochromatic or white illumination.

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