Organic compound and organic electroluminescent element using the same

Abstract

The present application relates to a novel organic compound and an organic electroluminescent element using the same, and more particularly to a compound having excellent electron injection and transport ability and an organic electroluminescent element having improved luminous efficiency, driving voltage, lifespan, and the like, and progressive driving voltage by including the compound in one or more organic layers.

Description

Technical Field

[0001] This invention relates to novel organic light-emitting compounds and organic electroluminescent devices utilizing the same, and more specifically, to compounds with excellent electron transport capabilities and organic electroluminescent devices in which characteristics such as luminous efficiency, driving voltage, lifetime, and progressive driving voltage are improved by including the compound in one or more organic layers. Background Technology

[0002] When a voltage is applied between two electrodes in an organic electroluminescent device (hereinafter referred to as an "organic EL device"), holes are injected from the anode and electrons are injected from the cathode into the organic layer. When the injected holes and electrons meet, they form excitons. When these excitons transition to the ground state, they emit light. The materials used in the organic layer can be classified according to their function as light-emitting materials, hole-injecting materials, hole-transporting materials, electron-transporting materials, and electron-injecting materials.

[0003] Materials forming the light-emitting layer of organic EL devices can be categorized into blue, green, and red light-emitting materials based on their emission color. Additionally, yellow and orange light-emitting materials are used to produce more natural colors. Furthermore, to increase luminous efficiency through increased color purity and energy transfer, a host / dopant system can be used as the light-emitting material. Dopants can be classified into fluorescent dopants using organic materials and phosphorescent dopants using metal coordination compounds containing heavy atoms such as Ir and Pt. Since the development of such phosphorescent materials can theoretically improve luminous efficiency by up to four times compared to fluorescence, not only phosphorescent dopants but also phosphorescent host materials are attracting considerable attention.

[0004] To date, NPB, BCP, Alq3, and other compounds represented by the following chemical formulas are widely known as hole injection layers, hole transport layers, hole blocking layers, and electron transport layers. Regarding luminescent materials, anthracene derivatives have been reported as fluorescent dopants / host materials. In particular, phosphorescent materials, such as Firpic, Ir(ppy)3, and (acac)Ir(btp)2, which offer advantages in improving efficiency, have been used as blue, green, and red dopants. Currently, CBP exhibits excellent properties as a phosphorescent host material.

[0005] However, while conventional materials offer advantages in luminescence properties, their low glass transition temperatures and poor thermal stability prevent them from achieving satisfactory lifetimes in organic EL devices. Therefore, there is a need to develop high-performance organic layer materials. Summary of the Invention

[0006] Technical issues

[0007] The purpose of this invention is to provide novel organic compounds that possess excellent electron injection and transport capabilities, electrochemical stability, and thermal stability, and can be used as organic electroluminescent elements, specifically as electron transport layer materials or N-type charge generation layer materials.

[0008] Another object of the present invention is to provide an organic electroluminescent element comprising the above-mentioned novel organic compound, exhibiting low driving voltage, high luminous efficiency, and improved lifetime.

[0009] Methods for solving problems

[0010] To achieve the above objectives, the present invention provides the following organic compounds represented by chemical formula 1:

[0011] [Chemical Formula 1]

[0012]

[0013] (In the above chemical formula 1,

[0014] R1 and R2 may be the same or different from each other, and are independently chosen from hydrogen, deuterium (D), and C1~C2. 60 Alkyl groups, C3~C 60 The group consists of cycloalkyl groups and heteroaryl groups with 5 to 60 nuclei, excluding cases where R1 and R2 are both hydrogen atoms.

[0015] L1 selects a free single key, C6~C 60 The group consists of arylene groups and heteroarylene groups with 5 to 60 nuclei.

[0016] Ar1 is selected from the group consisting of heteroaryl groups with 5 to 60 free atomic nuclei, -P(=O)(R3)(R4), and -Si(R5)(R6)(R7).

[0017] R3 to R7 may be the same as or different from each other, and are independently selected from hydrogen, deuterium, halogen group, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazino group, hydrazono group, C1~C6. 60 Alkyl groups, C2~C 60 alkenyl, C2~C 60 alkynyl group, C3~C 60 Cycloalkyl groups, heterocyclic alkyl groups with 3 to 60 nuclei, C3~C 60 Cycloalkenyl groups, heterocyclic alkenyl groups with 3 to 60 nuclei, C6~C 60 aryl groups, heteroaryl groups with 5 to 60 nuclei, C1~C60 alkoxy groups, C6~C 60 aryloxy groups, C1~C 60 alkylsilyl, C6~C 60 arylsilyl, C1~C 40 alkylboron group, C6~C 60 arylboryl group, C6~C 60 arylphosphine, C6~C 60 arylphosphine oxide and C6~C 60 The group composed of aryl amino groups.

[0018] The alkyl, cycloalkyl, and heteroaryl groups of R1 and R2, the arylene and heteroarylene groups of L1, the heteroaryl groups of Ar1, and the hydrazyl, hydrazone, alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, cycloalkenyl, heterocycloalkenyl, aryl, heteroaryl, alkoxy, aryloxy, alkylsilyl, arylsilyl, alkylboryl, arylboryl, arylphosphinyl, arylphosphine oxide, and arylamino groups of R3 to R7 are each independently replaced by deuterium, halogen, hydroxyl, cyano, nitro, amino, amidino group, hydrazino group, hydrazono group, C1~C 60 Alkyl groups, C2~C 60 alkenyl, C2~C 60 alkynyl group, C3~C 60 Cycloalkyl groups, heterocyclic alkyl groups with 3 to 60 nuclei, C3~C 60 Cycloalkenyl groups, heterocyclic alkenyl groups with 3 to 60 nuclei, C6~C 60 aryl groups, heteroaryl groups with 5 to 60 nuclei, C1~C 60 alkoxy groups, C6~C 60 aryloxy groups, C1~C 60 alkylsilyl, C6~C 60 arylsilyl, C1~C 40 alkylboron group, C6~C 60 arylboryl group, C6~C 60 arylphosphine, C6~C 60 arylphosphine oxide and C6~C 60 The group consisting of arylamine groups has one or more substituents that are substituted or unsubstituted, where, when there are multiple substituents, they are either the same as or different from each other.

[0019] Furthermore, the present invention provides an organic electroluminescent element comprising an anode, a cathode, and one or more organic layers between the anode and the cathode, wherein at least one of the organic layers comprises the aforementioned organic compound. In this case, the organic layer comprising the aforementioned compound can be an electron transport layer.

[0020] In addition, the present invention provides an organic electroluminescent element comprising an anode and a cathode arranged spaced apart from each other; a plurality of light-emitting units between the anode and the cathode; an N-type charge-generating layer and a P-type charge-generating layer between adjacent light-emitting units, wherein each light-emitting unit comprises a hole transport layer, a light-emitting layer and an electron transport layer, and the N-type charge-generating layer comprises the aforementioned compound.

[0021] Invention Effects

[0022] The compounds of the present invention exhibit excellent electron transport capabilities, luminescence efficiency, electrochemical stability, and thermal stability, and therefore can be used as organic layer materials for organic electroluminescent devices. In particular, when the compounds of the present invention are used as at least one of electron transport layer materials, electron transport auxiliary layer materials, and N-type charge generation layer materials, compared with conventional materials, it is possible to manufacture organic electroluminescent devices with excellent luminescence performance, low driving voltage, high efficiency, and long lifetime characteristics, and further, it is also possible to manufacture full-color display panels with improved performance and lifetime. Attached Figure Description

[0023] Figure 1 This is a schematic cross-sectional view of an organic electroluminescent element according to a first embodiment of the present invention.

[0024] Figure 2 This is a schematic cross-sectional view of an organic electroluminescent element according to a second embodiment of the present invention.

[0025] Figure 3 This is a schematic cross-sectional view of an organic electroluminescent element according to a third embodiment of the present invention.

[0026] Figure 4 This is a schematic cross-sectional view of an organic electroluminescent element according to a fourth embodiment of the present invention.

[0027] **Symbol Explanation**

[0028] 100: Anode, 200: Cathode

[0029] 300: Organic layer; 310: Hole injection layer.

[0030] 320: Hole transport layer, 330: Emissive layer

[0031] 340: Electron transport layer; 350: Electron injection layer.

[0032] 360: Electron transmission auxiliary layer; 400: First light-emitting unit.

[0033] 410: First hole transport layer; 420: First luminescent layer.

[0034] 430: First electron transport layer; 440: Hole injection layer.

[0035] 500: Second light-emitting unit; 510: Second hole transport layer.

[0036] 520: Second light-emitting layer; 530: Second electron transport layer.

[0037] 600: Charge generation layer, 610: N-type charge generation layer

[0038] 620: P-type charge generation layer. Detailed Implementation

[0039] The present invention will now be described.

[0040] <Novel Compounds>

[0041] This invention provides novel compounds that possess excellent electron injection and transport capabilities, electrochemical stability, and thermal stability, which can improve the high efficiency, long lifetime, driving voltage characteristics, and progressive driving voltage characteristics of organic electroluminescent elements. These compounds can be used as electron transport layer materials, electron transport auxiliary layer materials, or N-type charge generation layer materials.

[0042] Specifically, the compound represented by the above chemical formula 1 contains a basic structure formed by directly or indirectly introducing various heteroaryl groups (especially electron-withdrawing (EWG) groups), phosphine oxides, or silyl groups at position 4 of the phenanthroline moiety, and introducing alkyl, cycloalkyl, etc., at positions 2 and 9. Here, the carbon / nitrogen position numbering of the phenanthroline moiety can be as follows.

[0043]

[0044] In the compounds of the present invention, the phenanthroline moiety comprises nitrogen (N) with relatively electron-rich sp2 hybrid orbitals. In particular, the phenanthroline moiety has a structure with two nitrogen atoms adjacent to each other, thus enabling it to form covalent bonds with surrounding hydrogen (H) or coordinate bonds with alkali metals or alkaline earth metals such as Li and Yb. When the compounds of Formula 1 containing such phenanthroline moiety are applied to electron transport layers or N-type charge generation layers, the phenanthroline moiety traps the doped alkali metal or alkaline earth metal, increasing the intramolecular electron density and thereby improving electron injection and transport capabilities. For example, when the compounds of the present invention are applied to the N-type charge generation layer of an OLED, the nitrogen of the phenanthroline moiety can bind with the alkali metal or alkaline earth metal acting as a dopant in the N-type charge generation layer to form a band gap state. In particular, even when used alone as the host material of the N-type charge generation layer without mixing with other host materials, the compounds of the present invention can smoothly transfer electrons from the N-type charge generation layer to the electron transport layer by means of the band gap state. Furthermore, when the compounds of the present invention are applied to the electron transport layer of an OLED, electrons can be smoothly transferred to the light-emitting layer side. Therefore, when the compounds of the present invention are used as N-type charge generation layer materials or electron transport layer materials, the driving voltage of organic electroluminescent elements can be reduced, luminous efficiency can be improved, and long lifetime can be achieved.

[0045] Furthermore, the phenanthroline moiety of the above-mentioned compounds is a highly electron-withdrawing moiety, and therefore can be used as an electron-withdrawing group (EWG). A heteroaryl group [especially a highly electron-withdrawing EWG], a phosphono group, or a silyl group is introduced directly or via a linking group at the 4 position of such a phenanthroline moiety. In particular, by introducing a highly electron-withdrawing EWG at the 4 position of the phenanthroline moiety, the compounds of the present invention can maximize electron injection and transport capabilities due to increased electron mobility. Therefore, when the compounds of the present invention are applied to organic electroluminescent devices, not only can low driving voltage, high current efficiency, and long lifetime characteristics be achieved, but progressive driving voltage characteristics can also be improved to prevent increased power consumption and decreased lifetime of the device.

[0046] Furthermore, the phenanthrene moiety of the above-mentioned compounds can improve thermal stability by introducing substituents such as alkyl or cycloalkyl groups at the active sites, namely positions 2 and 9, respectively, thereby blocking the active site. However, compounds with aryl groups introduced at positions 2 and / or 9 of the phenanthrene moiety have an increased sublimation temperature due to the increased molecular weight, which may damage the organic light-emitting element due to excessive heat used to sublimate the compound during manufacturing. Therefore, it is preferable to introduce alkyl or cycloalkyl groups, especially short-chain alkyl or cycloalkyl groups, at positions 2 and / or 9 of the phenanthrene moiety compared to aryl groups. Such compounds of the present invention can block the active site with minimal increase in molecular weight, thus improving thermal stability without element degradation. In addition, the compounds of the present invention have a lower sublimation temperature compared to compounds with aryl groups introduced at positions 2 and 9 of the phenanthrene moiety. Therefore, the compounds of the present invention can improve thermal stability while preventing element degradation during manufacturing.

[0047] As described above, the compound represented by Chemical Formula 1 of the present invention exhibits excellent electron injection and transport capabilities. Therefore, the compound of the present invention can be used as an organic layer material, preferably an electron transport layer material, in organic electroluminescent devices. Furthermore, the compound of the present invention can be used as an N-type charge generation layer material in tandem organic electroluminescent devices. Thus, when the compound represented by Chemical Formula 1 of the present invention is used as an electron transport layer material or an N-type charge generation layer material in an organic electroluminescent device, not only can the device's driving voltage, luminous efficiency, and lifetime characteristics be improved, but also the progressive increase in driving voltage can be prevented, thereby optimizing the performance of a full-color organic light-emitting panel using the aforementioned organic electroluminescent device.

[0048] In the compounds represented by the above chemical formula 1, R1 and R2 may be the same or different from each other, and are independently selected from hydrogen, deuterium (D), and C1~C2. 60 Alkyl groups, C3~C 60 The group consisting of cycloalkyl groups and heteroaryl groups with 5 to 60 nuclei, excluding cases where both R1 and R2 are hydrogen atoms. Unlike compounds where both R1 and R2 are hydrogen atoms, compounds of this formula 1 have a portion, preferably all, of the active site of the phenanthrene moiety blocked, thus improving thermal stability. Furthermore, unlike compounds where R1 and R2 are aryl groups, the compounds of this formula 1 block the active site by a minimum increase in molecular weight, thus improving thermal stability without component degradation.

[0049] As an example, at least one of R1 and R2 mentioned above can be C1~C 60 Alkyl groups.

[0050] As another example, R1 and R2 mentioned above may be the same as or different from each other, and each can be independently C1~C1. 20 Alkyl groups.

[0051] As another example, R1 and R2 are identical to each other and can be C1-C6 alkyl groups. Specifically, the C1-C6 alkyl groups can be selected from the group consisting of methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, and tert-butyl.

[0052] The alkyl, cycloalkyl, aryl, and heteroaryl groups of R1 and R2 are each independently selected from deuterium, halogen, hydroxyl, cyano, nitro, amino, amidino group, hydrazino group, hydrazono group, C1~C 60 Alkyl groups, C2~C 60 alkenyl, C2~C 60 alkynyl group, C3~C 60 Cycloalkyl groups, heterocyclic alkyl groups with 3 to 60 nuclei, C3~C 60 Cycloalkenyl groups, heterocyclic alkenyl groups with 3 to 60 nuclei, C6~C 60 aryl groups, heteroaryl groups with 5 to 60 nuclei, C1~C 60 alkoxy groups, C6~C 60 aryloxy groups, C1~C 60 alkylsilyl, C6~C 60 arylsilyl, C1~C 40 alkylboron group, C6~C 60 arylboryl group, C6~C 60 arylphosphine, C6~C 60 arylphosphine oxide and C6~C 60 The arylamine group is substituted or unsubstituted with one or more substituents, where, when there are multiple substituents, they are either the same as or different from each other. Here, the heterocyclic alkyl and heteroaryl groups each contain one or more heteroatoms selected from the group consisting of N, S, O, and Se.

[0053] Based on R1 and R2, the compound represented by the above chemical formula 1 can be a compound represented by any of the following chemical formulas 2 to 5, but is not limited thereto.

[0054] [Chemical Formula 2]

[0055]

[0056] [Chemical Formula 3]

[0057]

[0058] [Chemical Formula 4]

[0059]

[0060] [Chemical Formula 5]

[0061]

[0062] Among the above chemical formulas 2 to 5,

[0063] L1 and Ar1 are defined in the above chemical formula 1.

[0064] R2 can be a C1-C6 alkyl group, specifically selected from the group consisting of methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, and tert-butyl, and more specifically, methyl. In this case, R2 can be the same as or different from the substituents of formulas 2-5 corresponding to R1 in the above chemical formula 1.

[0065] According to one example, in the compounds of chemical formulas 2 to 5 above, R2 is a C1 to C6 alkyl group, specifically selected from the group consisting of methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, and tert-butyl, in which case it is the same as the substituents of chemical formulas 2 to 5 corresponding to R1 of chemical formula 1 above.

[0066] In the above chemical formula 1, L1 is selected from single bonds and C6~C6 bonds. 60 It is a group composed of arylene groups and heteroarylene groups with 5 to 60 nuclei, specifically consisting of single bonds or selected from C6 to C6. 30 It is a group composed of arylene groups and heteroarylene groups with 5 to 30 nuclei.

[0067] The aforementioned L1 arylene and heteroarylene groups are each independently selected from deuterium, halogen group, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazino group, hydrazono group, C1~C1. 60 Alkyl groups, C2~C 60 alkenyl, C2~C 60 alkynyl group, C3~C 60 Cycloalkyl groups, heterocyclic alkyl groups with 3 to 60 nuclei, C3~C 60 Cycloalkenyl groups, heterocyclic alkenyl groups with 3 to 60 nuclei, C6~C 60 aryl groups, heteroaryl groups with 5 to 60 nuclei, C1~C 60 alkoxy groups, C6~C 60 aryloxy groups, C1~C 60 alkylsilyl, C6~C 60 arylsilyl, C1~C40 alkylboron group, C6~C 60 arylboryl group, C6~C 60 arylphosphine, C6~C 60 arylphosphine oxide and C6~C 60 One or more substituents in the group consisting of arylamine groups are substituted or unsubstituted, and when there are multiple substituents, they are the same as or different from each other.

[0068] As an example, L1 above can be C6~C 60 Alpha-aryl compounds.

[0069] As another example, the L1 mentioned above can be a linking group represented by the following chemical formula L.

[0070] [Chemical formula L]

[0071]

[0072] In the above chemical formula L,

[0073] n is an integer from 0 to 3.

[0074] a is an integer from 0 to 4.

[0075] When there are multiple R3s, they may be the same as or different from each other.

[0076] R3 is selected from hydrogen, deuterium, halogen group, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazino group, hydrazono group, C1~C 60 Alkyl groups, C2~C 60 alkenyl, C2~C 60 alkynyl group, C3~C 60 Cycloalkyl groups, heterocyclic alkyl groups with 3 to 60 nuclei, C3~C 60 Cycloalkenyl groups, heterocyclic alkenyl groups with 3 to 60 nuclei, C6~C 60 aryl groups, heteroaryl groups with 5 to 60 nuclei, C1~C 60 alkoxy groups, C6~C 60 aryloxy groups, C1~C 60 alkylsilyl, C6~C 60 arylsilyl, C1~C 40 alkylboron group, C6~C 60 arylboryl group, C6~C 60 arylphosphine, C6~C 60 arylphosphine oxide and C6~C 60 It is a group composed of aryl amino groups.

[0077] As another example, L1 can be selected from the group consisting of the following linking groups L1 to L4. In this case, the phenanthroline moiety of the compound of the present invention is bonded to the substituent Ar1 at the para or meta position, or at the para-para or meta-meta position, with the linking group as the center. Thus, the compound of the present invention can form a plate-like structure, inducing intermolecular stacking, thereby increasing electron mobility and exhibiting superior electron transport properties. Furthermore, the interaction between the phenanthroline moiety and the substituent Ar1 in the compound of the present invention is minimized, increasing the structural stability of the molecule and minimizing steric hindrance, thereby effectively improving the physical, electrochemical, and thermal stability of the compound itself. In addition, compared to compounds in which the phenanthroline moiety and the substituent Ar1 are bonded at the ortho position or introduced at the ortho position with the linking group as the center, the compound of the present invention also has an effect on inhibiting the crystallization of the organic layer, thus significantly improving the durability and lifetime characteristics of organic electroluminescent devices.

[0078]

[0079] The hydrogen atoms in the linking groups L1 to L4 can be deuterium (D), halogens, cyano groups, nitro groups, or C1 to C4 groups. 12 Alkyl, C6~C 10 It can be substituted with one or more substituents such as aryl or heteroaryl with 5 to 9 nuclei.

[0080] In the above chemical formula 1, Ar1 is selected from the group consisting of heteroaryl groups with 5 to 60 free atomic nuclei, -P(=O)(R3)(R4) and -Si(R5)(R6)(R7).

[0081] As an example, Ar1 can be a heteroaryl group with 5 to 60 nuclei. In particular, when Ar1 is an electron-withdrawing group (EWG), the compounds of Formula 1 described above can maximize electron injection and transport capabilities due to the further increase in electron mobility. Furthermore, when the organic layer (e.g., the N-type charge-generating layer) of an OLED using a compound of Formula 1 with Ar1 as EWG has a deep LUMO value in adjacent organic layers (e.g., electron transport layers), electron injection is more efficient compared to when Ar1 is -P(=O)(R3)(R4) or -Si(R5)(R6)(R7). However, when the organic layer (e.g., the electron transport layer, etc.) of an OLED using a triazine or pyrimidinyl compound with EWG has a deeper LUMO value compared to the organic layer (e.g., the electron transport layer, etc.) of an OLED using the compounds of Formula 1 of the present invention, electron movement may be difficult. Therefore, Ar1 is preferably a heteroaryl group with 5 to 60 nuclei (specifically, a heteroaryl group with 5 to 30 nuclei), in which case triazine and pyrimidinyl groups are excluded. Examples of such EWGs include substituents represented by the following chemical formulas S1 to S6, but are not limited to these.

[0082] R3 to R7 may be the same as or different from each other, and are each independently selected from hydrogen, deuterium, halogen group, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazino group, hydrazono group, C1~C6. 60 Alkyl groups, C2~C 60 alkenyl, C2~C 60 alkynyl group, C3~C 60 Cycloalkyl groups, heterocyclic alkyl groups with 3 to 60 nuclei, C3~C 60 Cycloalkenyl groups, heterocyclic alkenyl groups with 3 to 60 nuclei, C6~C 60 aryl groups, heteroaryl groups with 5 to 60 nuclei, C1~C 60 alkoxy groups, C6~C 60 aryloxy groups, C1~C 60 alkylsilyl, C6~C 60 arylsilyl, C1~C 40 alkylboron group, C6~C 60 arylboryl group, C6~C 60 arylphosphine, C6~C 60 arylphosphine oxide and C6~C 60The group consisting of arylamine groups. Specifically, R3 to R7 may be the same as or different from each other, and each may be independently selected from deuterium, halogen, hydroxyl, cyano, nitro, amino, amidino group, hydrazino group, hydrazono group, C1~C1 groups. 20 Alkyl groups, C2~C 20 alkynyl group, C3~C 20 Cycloalkyl groups, heterocyclic alkyl groups with 3 to 30 nuclei, C3~C 20 Cycloalkenyl groups, heterocyclic alkenyl groups with 3 to 30 nuclei, C6~C 30 aryl groups, heteroaryl groups with 5 to 30 nuclei, C1~C 30 Alkyl groups and C6~C 30 The group composed of aryl groups.

[0083] As an example, R3 to R7 mentioned above may be the same as or different from each other, and each can independently be C6 to C7. 30 The aryl group can be C6~C 30 Aryl groups. Examples of such aryl groups include phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, anthracene, tetraphenyl, pyrene, etc. Basic, but not limited to.

[0084] The aryl and heteroaryl groups of Ar1, and the hydrazyl, hydrazone, alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, cycloalkenyl, heterocycloalkenyl, aryl, heteroaryl, alkoxy, aryloxy, alkylsilyl, arylsilyl, alkylboronyl, arylboronyl, arylphosphinyl, arylphosphine oxide, and arylamino groups of R3 to R7 are each independently selected from deuterium, halogen, hydroxyl, cyano, nitro, amino, amidino group, hydrazino group, hydrazono group, C1~C 60 Alkyl groups, C2~C 60 alkenyl, C2~C 60 alkynyl group, C3~C 60 Cycloalkyl groups, heterocyclic alkyl groups with 3 to 60 nuclei, C3~C 60 Cycloalkenyl groups, heterocyclic alkenyl groups with 3 to 60 nuclei, C6~C 60 aryl groups, heteroaryl groups with 5 to 60 nuclei, C1~C 60 alkoxy groups, C6~C 60 aryloxy groups, C1~C 60 alkylsilyl, C6~C 60 arylsilyl, C1~C 40 alkylboron group, C6~C60 arylboryl group, C6~C 60 arylphosphine, C6~C 60 arylphosphine oxide and C6~C 60 One or more substituents in the group consisting of arylamine groups are substituted or unsubstituted, and when there are multiple substituents, they are the same as or different from each other.

[0085] Specifically, the Ar1 mentioned above can be a substituent selected from any of the following chemical formulas S1 to S8, but is not limited thereto.

[0086]

[0087] In the above chemical formulas S1 to S8,

[0088] X1 to X4 may be the same as or different from each other, and each is independently N or C (Ar7), wherein at least two of X1 to X3 are N, and at least two of X2 to X4 are N.

[0089] Y1 is either S or O.

[0090] Z1 to Z3 may be the same as or different from each other, and each is independently N, N(Ar8), C, C(Ar9), C(Ar8). 10 (Ar) 11 ), wherein at least two of Z1 to Z3 are independently N or N(Ar8),

[0091] W1 to W3 may be the same as or different from each other, and each is independently N or C (Ar). 12 ), where at least two of W1 to W3 are N,

[0092] Ar2 to Ar 12 Each group is independently selected from hydrogen, deuterium, halogen group, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazino group, hydrazono group, C1~C. 60 Alkyl groups, C2~C 60 alkenyl, C2~C 60 alkynyl group, C3~C 60 Cycloalkyl groups, heterocyclic alkyl groups with 3 to 60 nuclei, C3~C 60 Cycloalkenyl groups, heterocyclic alkenyl groups with 3 to 60 nuclei, C6~C 60 aryl groups, heteroaryl groups with 5 to 60 nuclei, C1~C 60 alkoxy groups, C6~C 60 aryloxy groups, C1~C 60 alkylsilyl, C6~C 60arylsilyl, C1~C 40 alkylboron group, C6~C 60 arylboryl group, C6~C 60 arylphosphine, C6~C 60 arylphosphine oxide and C6~C 60 The group composed of aryl amino groups.

[0093] a is an integer from 0 to 4.

[0094] Multiple R3s may be the same or different from each other.

[0095] R3 is independently selected from hydrogen, deuterium, halogen group, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazino group, hydrazono group, C1~C 60 Alkyl groups, C2~C 60 alkenyl, C2~C 60 alkynyl group, C3~C 60 Cycloalkyl groups, heterocyclic alkyl groups with 3 to 60 nuclei, C3~C 60 Cycloalkenyl groups, heterocyclic alkenyl groups with 3 to 60 nuclei, C6~C 60 aryl groups, heteroaryl groups with 5 to 60 nuclei, C1~C 60 alkoxy groups, C6~C 60 aryloxy groups, C1~C 60 alkylsilyl, C6~C 60 arylsilyl, C1~C 40 alkylboron group, C6~C 60 arylboryl group, C6~C 60 arylphosphine, C6~C 60 arylphosphine oxide and C6~C 60 The group composed of aryl amino groups.

[0096] x is 0 or 1.

[0097] The above Ar2 to Ar 12 The hydrazinyl, hydrazone, alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, cycloalkenyl, heterocycloalkenyl, aryl, heteroaryl, alkoxy, aryloxy, alkylsilyl, arylsilyl, alkylboryl, arylboryl, arylphosphinyl, arylphosphine oxide, and arylamino groups are each independently selected from deuterium, halogen, hydroxyl, cyano, nitro, amino, amidino group, hydrazino group, hydrazono group, C1~C 60 Alkyl groups, C2~C 60 alkenyl, C2~C60 alkynyl group, C3~C 60 Cycloalkyl groups, heterocyclic alkyl groups with 3 to 60 nuclei, C3~C 60 Cycloalkenyl groups, heterocyclic alkenyl groups with 3 to 60 nuclei, C6~C 60 aryl groups, heteroaryl groups with 5 to 60 nuclei, C1~C 60 alkoxy groups, C6~C 60 aryloxy groups, C1~C 60 alkylsilyl, C6~C 60 arylsilyl, C1~C 40 alkylboron group, C6~C 60 arylboryl group, C6~C 60 arylphosphine, C6~C 60 arylphosphine oxide and C6~C 60 One or more substituents in the group consisting of arylamine groups are substituted or unsubstituted, and when there are multiple substituents, they are the same as or different from each other.

[0098] In particular, the substituents of the above chemical formulas S1 to S6 can be specified as substituents represented by the following chemical formulas SS1 to SS9, but are not limited thereto.

[0099]

[0100] Among the above chemical formulas SS1 to SS9,

[0101] Ar7, Ar8, Ar 12 R3 and a are defined in the same way as those in the above chemical formulas S1 to S6.

[0102] The compound represented by chemical formula 1 of the present invention may be embodied as a compound represented by any of the following chemical formulas 6 to 11, but is not limited thereto.

[0103] [Chemical Formula 6]

[0104]

[0105] [Chemical Formula 7]

[0106]

[0107] [Chemical Formula 8]

[0108]

[0109] [Chemical Formula 9]

[0110]

[0111] [Chemical Formula 10]

[0112]

[0113] [Chemical Formula 11]

[0114]

[0115] In the above chemical formulas 6 to 11,

[0116] R1 and R2 may be the same as or different from each other, and each is an alkyl group that is C1 to C6.

[0117] m is 0 or 1.

[0118] X1 to X4 may be the same as or different from each other, and each is independently N or C (Ar7), wherein at least two of X1 to X3 are N, and at least two of X2 to X4 are N.

[0119] Y1 is either S or O.

[0120] Z1 to Z3 may be the same as or different from each other, and each is independently N, N(Ar8), C, C(Ar9), C(Ar8). 10 (Ar) 11 ), wherein at least two of Z1 to Z3 are independently N or N(Ar8),

[0121] W1 to W3 may be the same as or different from each other, and each is independently N or C (Ar). 12 ), where at least two of W1 to W3 are N,

[0122] Ar7 to Ar 12 Each group is independently selected from hydrogen, deuterium, halogen group, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazino group, hydrazono group, C1~C. 60 Alkyl groups, C2~C 60 alkenyl, C2~C 60 alkynyl group, C3~C 60 Cycloalkyl groups, heterocyclic alkyl groups with 3 to 60 nuclei, C3~C 60 Cycloalkenyl groups, heterocyclic alkenyl groups with 3 to 60 nuclei, C6~C 60 aryl groups, heteroaryl groups with 5 to 60 nuclei, C1~C 60 alkoxy groups, C6~C 60 aryloxy groups, C1~C 60 alkylsilyl, C6~C 60 arylsilyl, C1~C 40 alkylboron group, C6~C 60arylboryl group, C6~C 60 arylphosphine, C6~C 60 arylphosphine oxide and C6~C 60 The group composed of aryl amino groups.

[0123] a is an integer from 0 to 4.

[0124] Multiple R3s may be the same or different from each other.

[0125] R3 is independently selected from hydrogen, deuterium, halogen group, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazino group, hydrazono group, C1~C 60 Alkyl groups, C2~C 60 alkenyl, C2~C 60 alkynyl group, C3~C 60 Cycloalkyl groups, heterocyclic alkyl groups with 3 to 60 nuclei, C3~C 60 Cycloalkenyl groups, heterocyclic alkenyl groups with 3 to 60 nuclei, C6~C 60 aryl groups, heteroaryl groups with 5 to 60 nuclei, C1~C 60 alkoxy groups, C6~C 60 aryloxy groups, C1~C 60 alkylsilyl, C6~C 60 arylsilyl, C1~C 40 alkylboron group, C6~C 60 arylboryl group, C6~C 60 arylphosphine, C6~C 60 arylphosphine oxide and C6~C 60 The group composed of aryl amino groups.

[0126] x is 0 or 1.

[0127] The aforementioned Ar7 to Ar 12 The hydrazinyl, hydrazone, alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, cycloalkenyl, heterocycloalkenyl, aryl, heteroaryl, alkoxy, aryloxy, alkylsilyl, arylsilyl, alkylboryl, arylboryl, arylphosphinyl, arylphosphine oxide, and arylamino groups are each independently selected from deuterium, halogen, hydroxyl, cyano, nitro, amino, amidino group, hydrazino group, hydrazono group, C1~C 60 Alkyl groups, C2~C 60 alkenyl, C2~C 60 alkynyl group, C3~C 60Cycloalkyl groups, heterocyclic alkyl groups with 3 to 60 nuclei, C3~C 60 Cycloalkenyl groups, heterocyclic alkenyl groups with 3 to 60 nuclei, C6~C 60 aryl groups, heteroaryl groups with 5 to 60 nuclei, C1~C 60 alkoxy groups, C6~C 60 aryloxy groups, C1~C 60 alkylsilyl, C6~C 60 arylsilyl, C1~C 40 alkylboron group, C6~C 60 arylboryl group, C6~C 60 arylphosphine, C6~C 60 arylphosphine oxide and C6~C 60 One or more substituents in the group consisting of arylamine groups are substituted or unsubstituted, and when there are multiple substituents, they are the same as or different from each other.

[0128] The compounds represented by Chemical Formula 1 of the present invention can be specifically embodied as compounds selected from the group consisting of compounds A-1 to A-28, B-1 to B-24, C-1 to C-24, D-1 to D-24, E-1 to E-24, and F-1 to F-24. However, the compounds represented by Chemical Formula 1 of the present invention are not limited to the compounds exemplified below.

[0129]

[0130]

[0131]

[0132]

[0133]

[0134] In this invention, "alkyl" means a monovalent substituent derived from a straight-chain or branched saturated hydrocarbon having 1 to 40 carbon atoms. Examples of substituents include methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, isopentyl, hexyl, etc., but are not limited thereto.

[0135] In this invention, "alkenyl" means a monovalent substituent derived from a straight-chain or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and one or more carbon-carbon double bonds. Examples include vinyl, allyl, isopropenyl, and 2-butenyl, but are not limited thereto.

[0136] In this invention, "alkynyl" means a monovalent substituent derived from a straight-chain or branched unsaturated hydrocarbon with 2 to 40 carbon atoms having one or more carbon-carbon triple bonds. Examples of such substituents include ethynyl and 2-propynyl, but it is not limited to these.

[0137] In this invention, "cycloalkyl" means a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms. Examples of such cycloalkyl groups include cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine, etc., but are not limited thereto.

[0138] In this invention, "heterocyclic alkyl" means a monovalent substituent derived from a non-aromatic hydrocarbon with 3 to 40 nuclei, wherein one or more carbons in the ring, preferably 1 to 3 carbons, are replaced by heteroatoms such as N, O, S, or Se. Examples of such heterocyclic alkyl groups include morpholinoyl and piperazine, but are not limited thereto.

[0139] In this invention, "aryl" means a monovalent substituent derived from an aromatic hydrocarbon with 6 to 60 carbon atoms, consisting of a single ring or a combination of two or more rings. Furthermore, it may also include forms formed by simple attachment or condensation of two or more rings. Examples of such aryl groups include phenyl, naphthyl, phenanthryl, and anthracene, but are not limited to these.

[0140] In this invention, "heteroaryl" means a monovalent substituent derived from a mono- or poly-heterocyclic aromatic hydrocarbon with 5 to 60 atomic nuclei. In this case, one or more carbons in the ring, preferably 1 to 3 carbons, are replaced by heteroatoms such as N, O, S, or Se. Furthermore, it may include forms formed by simple attachment or condensation of two or more rings, and further may include forms condensed with an aryl group. Examples of such heteroaryl groups include 6-membered monocyclic groups such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl; polycyclic groups such as phenoxathienyl, indolizinyl, indolyl, purinyl, quinolyl, benzothiazole, and carbazolyl; and 2-furanyl, N-imidazolyl, and 2-iso-furanyl. Azolyl, 2-pyridyl, 2-pyrimidinyl, etc., but not limited to these.

[0141] In this invention, "alkoxy" means a monovalent substituent represented by R'O-, where R' is an alkyl group having 1 to 40 carbon atoms, and may include linear, branched, or cyclic structures. Examples of alkoxy groups include methoxy, ethoxy, n-propoxy, 1-propoxy, tert-butoxy, n-butoxy, pentoxy, etc., but are not limited to these.

[0142] In this invention, "aryloxy group" means a monovalent substituent represented by RO-, where R is an aryl group with 5 to 40 carbon atoms. Examples of such aryloxy groups include phenoxy, naphthoxy, and diphenoxy groups, but are not limited to these.

[0143] In this invention, "alkylsilyl" means a silyl group substituted with an alkyl group having 1 to 40 carbon atoms, including not only monoalkylsilyl groups but also dialkylsilyl groups and trialkylsilyl groups. Furthermore, "arylsilyl" means a silyl group substituted with an aryl group having 5 to 60 carbon atoms, including not only monoarylsilyl groups but also diarylsilyl groups, triarylsilyl groups, and other polyarylsilyl groups.

[0144] In this invention, "alkylboronyl" means a boron group substituted with an alkyl group having 1 to 40 carbon atoms, and "arylboronyl" means a boron group substituted with an aryl group having 6 to 60 carbon atoms.

[0145] In this invention, "alkylphosphine" means a phosphine group substituted with an alkyl group having 1 to 40 carbon atoms, including not only monoalkylphosphine groups but also dialkylphosphine groups. Furthermore, in this invention, "arylphosphine" means a phosphine group substituted with a monoaryl or diaryl group having 6 to 60 carbon atoms, including not only monoarylphosphine groups but also diarylphosphine groups.

[0146] In this invention, "arylamine" means an amine group that is replaced by an aryl group with 6 to 60 carbon atoms, including not only monoarylamines but also diarylamines.

[0147] In this invention, "heteroarylamine" means an amine group that is replaced by a heteroaryl group with 5 to 60 atomic nuclei, including not only mono-heteroarylamines but also di-heteroarylamines.

[0148] In this invention, "(aryl)(heteroaryl)amine" means an amine group substituted by an aryl group with 6 to 60 carbon atoms and a heteroaryl group with 5 to 60 nuclei.

[0149] In this invention, "condensed ring" means a condensed aliphatic ring with 3 to 40 carbon atoms, a condensed aromatic ring with 6 to 60 carbon atoms, a condensed aliphatic heterocycle with 3 to 60 nuclei, a condensed aromatic heterocycle with 5 to 60 nuclei, or a combination thereof.

[0150] Organic electroluminescent elements

[0151] On the other hand, the present invention provides an organic electroluminescent element (hereinafter referred to as "organic EL element") comprising a compound represented by the above chemical formula 1.

[0152] Figures 1 to 4 This is a schematic cross-sectional view of the organic electroluminescent element according to the first to fourth embodiments of the present invention.

[0153] The following is for reference Figures 1 to 3 The organic electroluminescent element of the first to third embodiments of the present invention will be described in detail below.

[0154] like Figures 1 to 3 As shown, the organic electroluminescent element of the present invention includes an anode 100, a cathode 200, and one or more organic layers 300 between the anode and the cathode, wherein at least one of the organic layers contains a compound represented by the above chemical formula 1. In this case, the above compound can be used alone or in combination of two or more.

[0155] The aforementioned organic layers 300 may include one or more of the following: a hole injection layer 310, a hole transport layer 320, a light-emitting layer 330, an electron transport auxiliary layer 360, an electron transport layer 340, and an electron injection layer 350, wherein at least one organic layer 300 comprises a compound represented by Chemical Formula 1. Specifically, the organic layer comprising the compound of Chemical Formula 1 may be an electron transport layer 340. That is, the compound represented by Chemical Formula 1 is included in the organic electroluminescent element as an electron transport layer material. In such an organic electroluminescent element, due to the compound of Chemical Formula 1, electrons are easily injected from the cathode or electron injection layer into the electron transport layer, and can rapidly move from the electron transport layer to the light-emitting layer, thus resulting in high binding force between holes and electrons in the light-emitting layer. Therefore, the organic electroluminescent element of the present invention exhibits excellent luminous efficiency, power efficiency, and brightness. Furthermore, the compound of Chemical Formula 1 exhibits excellent thermal stability and electrochemical stability, which can improve the performance of the organic electroluminescent element.

[0156] This compound of chemical formula 1 can be used alone or in combination with electron transport layer materials known in the art.

[0157] In this invention, the electron transport layer material that can be mixed with the compound of Formula 1 includes electron transport substances generally known in the art. As a non-limiting example of a usable electron transport substance, there are... azole compounds, isoazoles Azole compounds, triazole compounds, isothiazole compounds, Diazole compounds, thiadiazole compounds, perylene compounds, aluminum complexes (e.g., Alq3, tris(8-quinolinolato)-aluminium), gallium complexes (e.g., Gaq'2OPiv, Gaq'2OAc, 2(Gaq'2)), etc. They can be used alone or in combination of two or more.

[0158] In this invention, when the compound of the above chemical formula 1 is mixed with the electron transport layer material, there is no particular limitation on their mixing ratio, which can be appropriately adjusted within the range known in the art.

[0159] The structure of the organic electroluminescent element of the present invention is not particularly limited. For example, an anode 100, one or more organic layers 300, and a cathode 200 can be sequentially stacked on a substrate (see reference). Figures 1 to 3 Although not illustrated, it could also be a structure in which an insulating or adhesive layer is further inserted at the interface between the electrode and the organic layer.

[0160] As an example, organic electroluminescent elements such as Figure 1 The diagram shows a structure in which an anode 100, a hole injection layer 310, a hole transport layer 320, a light-emitting layer 330, an electron transport layer 340, and a cathode 200 are sequentially stacked on a substrate. Optionally, as shown... Figure 2 As shown, an electron injection layer 350 may be provided between the electron transport layer 340 and the cathode 200. Alternatively, an electron transport auxiliary layer 360 may be provided between the light-emitting layer 330 and the electron transport layer 340 (see reference). Figure 3 ).

[0161] Regarding the organic electroluminescent element of the present invention, except that at least one of the organic layers 300 described above [e.g., electron transport layer 340] contains a compound represented by the above chemical formula 1, the organic layers and electrodes can be formed and manufactured using materials and methods known in the art.

[0162] The aforementioned organic layer can be formed by vacuum evaporation or solution coating. Examples of solution coating methods include spin coating, dip coating, blade coating, inkjet printing, or thermal transfer, but are not limited to these.

[0163] The substrates that can be used in this invention are not particularly limited. As non-limiting examples, there are silicon wafers, quartz, glass plates, metal plates, plastic films and sheets, etc.

[0164] In addition, examples of anode materials include metals such as vanadium, chromium, copper, zinc, and gold, or their alloys; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; conductive polymers such as polythiophene, poly(3-methylthiophene), poly[3,4-(ethylidene-1,2-dioxothiophene] (PEDT), polypyrrole, or polyaniline; and carbon black, but are not limited to these.

[0165] In addition, examples of cathode materials include metals or alloys thereof such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver (Ag), tin or lead; and multilayered materials such as LiF / Al or LiO2 / Al, but are not limited to these.

[0166] Furthermore, there are no particular limitations on the hole injection layer, hole transport layer, light emission layer, and electron injection layer; commonly known materials in the art can be used.

[0167] The following is for reference Figure 4 The organic electroluminescent element of the fourth embodiment of the present invention will be described below.

[0168] like Figure 4 As shown, the organic electroluminescent element of the fourth embodiment of the present invention is a tandem element, comprising: an anode 100 and a cathode 200 facing each other; a plurality of light-emitting units 400 and 500 between the anode 100 and the cathode 200; and a charge-generating layer 600 between adjacent light-emitting units 400 and 500, comprising an N-type charge-generating layer 610 and a P-type charge-generating layer 620. In this case, the N-type charge-generating layer 610 comprises a compound represented by the above-described chemical formula 1.

[0169] Such a series-connected organic electroluminescent element has at least two light-emitting units, and the number of light-emitting units can be increased by inserting a charge-generating layer between adjacent light-emitting units.

[0170] According to one example, the plurality of light-emitting units may include a first light-emitting unit 400, a second light-emitting unit 500, ..., and an (m-1)th light-emitting unit (m = 3 or more, specifically 3 to 4). In this case, a charge-generating layer 600 comprising an N-type charge-generating layer 610 and a P-type charge-generating layer 620 is disposed between adjacent light-emitting units, wherein the N-type charge-generating layer 610 comprises the compound represented by the above chemical formula 1.

[0171] Specifically, the organic electroluminescent element of the present invention includes: an anode 100 and a cathode 200 facing each other; a first light-emitting unit 400 disposed on the anode 100; a second light-emitting unit 500 disposed on the first light-emitting unit 400; and a charge-generating layer 600 disposed between the first light-emitting unit 400 and the second light-emitting unit 500 and including an N-type charge-generating layer 610 and a P-type charge-generating layer 620. In this case, the N-type charge-generating layer 610 includes a compound represented by the above chemical formula 1.

[0172] Each light-emitting unit 400, 500 includes hole transport layers 410, 510, light-emitting layers 420, 520, and electron transport layers 430, 530. Specifically, the first light-emitting unit 400 may include a first hole transport layer 410, a first light-emitting layer 420, and a first electron transport layer 430, and the second light-emitting unit 500 may include a hole transport layer 510, a light-emitting layer 520, and an electron transport layer 530. Optionally, the first light-emitting unit 400 may further include a hole injection layer 440.

[0173] The hole transport layers 410 and 510, the light-emitting layers 420 and 520, the electron transport layers 430 and 530, and the hole injection layer 440 are not particularly limited and can be made of common materials known in the art.

[0174] The aforementioned charge generation layer (CGL) 600 is disposed between adjacent light-emitting units 400 and 500, thereby adjusting the charge between the light-emitting units 400 and 500 to achieve charge balance.

[0175] The charge generation layer 600 includes: an N-type charge generation layer 610 disposed adjacent to the first light-emitting unit 400 and supplying electrons to the first light-emitting unit 400; and a P-type charge generation layer 620 disposed adjacent to the second light-emitting unit 500 and supplying holes to the second light-emitting unit 500.

[0176] The aforementioned N-type charge generation layer 610 comprises a compound represented by Chemical Formula 1. The compound of Chemical Formula 1 exhibits excellent electron mobility and superior electron injection and transport capabilities. Therefore, when the compound of Chemical Formula 1 is used as an N-type charge generation layer material in an organic electroluminescent device, it is possible to prevent the progressive increase in driving voltage and the decrease in lifetime of the device.

[0177] According to one example, the aforementioned N-type charge generation layer 610 includes a host having electron transport properties, and the host is a compound represented by the aforementioned chemical formula 1. This N-type charge generation layer 610 of the present invention differs from an N-type charge generation layer containing two hosts, and can improve process efficiency when manufactured by co-evaporation.

[0178] The aforementioned N-type charge generation layer 610 may further contain an N-type dopant.

[0179] The N-type dopant that can be used in this invention is not particularly limited as long as it is a material commonly used in the art for generating N-type charge layers. For example, it includes alkali metals such as Li, Na, K, Rb, Cs, and Fr; alkaline earth metals such as Be, Mg, Ca, Sr, Ba, and Ra; Group 15 metals such as Bi (bismuth) and Sb (antimony); lanthanide metals such as La (lanthanum), Ce (cerium), Pr (praseodymium), Nd (neodymium), Pm (promethium), Sm (samarium), europium, Gd (gadolinium), Tb (terbium), Dy (dysprosium), Ho (holmium), Er (erbium), Tm (thulium), Yb (ytterbium), and Lu (lutetium); and one or more of the above-mentioned metal compounds. Alternatively, it can be an organic N-type dopant that has electron donor properties and is able to supply at least a portion of its electron charge to the organic host (e.g., a compound of chemical formula 1) to form a charge transfer complex with the organic host. Examples of such dopant include bis(ethylenedithio)tetrathiafulvalene (BEDT-TTF) and tetrathiafulvalene (TTF).

[0180] The thickness of the N-type charge generation layer 610 is not particularly limited; for example, it can be in the range of about 5 to 30 nm.

[0181] The aforementioned P-type charge generation layer 620 can be composed of a metal or an organic material doped with P-type. Here, the metals include Al, Cu, Fe, Pb, Zn, Au, Pt, W, In, Mo, Ni, and Ti, which can be used individually or in alloys of two or more. Furthermore, the P-type dopant and the host material used for the organic material doped with P-type are not particularly limited as long as they are commonly used materials. For example, the P-type dopant includes 2,3,5,6-tetrafluoro-7,7,8,8-tetracyano-quinodimethane (F4-TCNQ), iodine, FeCl3, FeF3, and SbCl5, which can be used individually or in mixtures of two or more. In addition, non-limiting examples of the aforementioned subjects include N,N'-bis(naphthaen-1-yl)-N,N'-bis(phenyl)-benzidine (NPB), N,N'-bis(3-methylphenyl)N,N'-bis(phenyl)-benzidine (TPD), and N,N,N',N'-tetra-naphthalenyl-benzidine (TNB), which can be used alone or in combination of two or more.

[0182] The descriptions of the anode 100 and cathode 200 are the same as those in the first to third embodiments described above, and therefore are omitted.

[0183] The present invention will be described in detail below through embodiments, as follows. However, the following embodiments are merely illustrative of the present invention, and the present invention is not limited to the following embodiments.

[0184] [Synthetic Example 1] Synthesis of Compound A-1

[0185]

[0186] 4-Chloro-2,9-dimethyl-1,10-phenanthroline (5 g, 20.6 mmol), 2-phenyl-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)benzo[4,5]thieno[3,2-d]pyrimidine (9.6 g, 20.6 mmol), Pd(OAc)2 (0.2 g, 1.0 mmol), Xphos (1.0 g, 2.1 mmol), and Cs2CO3 (13.5 g, 41.3 mmol) were placed in toluene (50 ml), EtOH (10 ml), and H2O (10 ml) and heated under reflux for 12 hours. After the reaction was complete, the mixture was extracted with dichloromethane and filtered through MgSO4. After removing the solvent from the filtered organic layer, the target compound (9.0 g, yield: 80%) was obtained by column chromatography.

[0187] [LCMS]: 545

[0188] [Synthesis Example 2] Synthesis of Compound A-2

[0189]

[0190] Instead of 2-phenyl-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)benzo[4,5]thieno[3,2-d]pyrimidine used in Synthesis Example 1, 2-phenyl-4-(3-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)benzo[4,5]thieno[3,2-d]pyrimidine was used, and the same procedure as in Synthesis Example 1 was performed to obtain the target compound (8.9 g, yield: 79%).

[0191] [LCMS]: 545

[0192] [Synthesis Example 3] Synthesis of Compound A-5

[0193]

[0194] Instead of 2-phenyl-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)benzo[4,5]thieno[3,2-d]pyrimidine used in Synthesis Example 1, 2-phenyl-4-(3-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)benzofuran[3,2-d]pyrimidine was used, and the same procedure as in [Synthesis Example 1] was performed to obtain the target compound (8.2 g, yield: 75%).

[0195] [LCMS]:529

[0196] [Synthetic Example 4] Synthesis of Compound A-7

[0197]

[0198] Instead of 2-phenyl-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)benzo[4,5]thieno[3,2-d]pyrimidine used in Synthesis Example 1, 4-phenyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)benzo[4,5]thieno[3,2-d]pyrimidine was used, and the same procedure as in Synthesis Example 1 was performed to obtain the target compound (8.5 g, yield: 76%).

[0199] [LCMS]: 545

[0200] [Synthesis Example 5] Synthesis of Compound A-8

[0201]

[0202] Instead of 2-phenyl-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)benzo[4,5]thieno[3,2-d]pyrimidine used in Synthesis Example 1, 4-phenyl-2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)benzo[4,5]thieno[3,2-d]pyrimidine was used, and the same procedure as in Synthesis Example 1 was performed to obtain the target compound (8.5 g, yield: 76%).

[0203] [LCMS]: 545

[0204] [Synthetic Example 6] Synthesis of Compound A-13

[0205]

[0206] Instead of 2-phenyl-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)benzo[4,5]thieno[3,2-d]pyrimidine used in Synthesis Example 1, 6,8-diphenyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)-[1,2,4]triazolo[1,5-a]pyridine was used, except that the same process as in [Synthesis Example 1] was performed to obtain the target compound (8.0 g, yield: 70%).

[0207] [LCMS]: 554

[0208] [Synthesis Example 7] Synthesis of Compound A-14

[0209]

[0210] Instead of 2-phenyl-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)benzo[4,5]thieno[3,2-d]pyrimidine used in Synthesis Example 1, 6,8-diphenyl-2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)-[1,2,4]triazolo[1,5-a]pyridine was used, except that the same process as in [Synthesis Example 1] was performed to obtain the target compound (8.0 g, yield: 70%).

[0211] [LCMS]: 554

[0212] [Synthetic Example 8] Synthesis of Compound A-16

[0213]

[0214] Instead of 2-phenyl-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)benzo[4,5]thieno[3,2-d]pyrimidine used in Synthesis Example 1, 6-phenyl-2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)-[1,2,4]triazolo[1,5-a]pyridine was used, except that the same process as in [Synthesis Example 1] was performed to obtain the target compound (7.1 g, yield: 72%).

[0215] [LCMS]:478

[0216] [Synthetic Example 9] Synthesis of Compound A-17

[0217]

[0218] Instead of 2-phenyl-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)benzo[4,5]thieno[3,2-d]pyrimidine used in Synthesis Example 1, 8-phenyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)-[1,2,4]triazolo[1,5-a]pyridine was used, and the same procedure as in [Synthesis Example 1] was performed to obtain the target compound (7.1 g, yield: 72%).

[0219] [LCMS]:478

[0220] [Synthetic Example 10] Synthesis of Compound A-19

[0221]

[0222] Instead of 2-phenyl-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)benzo[4,5]thieno[3,2-d]pyrimidine used in Synthesis Example 1, 2,3,5-triphenyl-6-(4-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)pyrazine was used, except that the same procedure as in [Synthesis Example 1] was performed to obtain the target compound (9.2 g, yield: 76%).

[0223] [LCMS]: 591

[0224] [Synthetic Example 11] Synthesis of Compound A-20

[0225]

[0226] Instead of 2-phenyl-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)benzo[4,5]thieno[3,2-d]pyrimidine used in Synthesis Example 1, 2,3,5-triphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)pyrazine was used, except that the same process as in [Synthesis Example 1] was performed to obtain the target compound (9.2 g, yield: 76%).

[0227] [LCMS]: 591

[0228] [Synthetic Example 12] Synthesis of Compound A-22

[0229]

[0230] Instead of 2-phenyl-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)benzo[4,5]thieno[3,2-d]pyrimidine used in Synthesis Example 1, 4-phenyl-2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)quinazoline was used, and the same procedure as in [Synthesis Example 1] was performed to obtain the target compound (7.1 g, yield: 71%).

[0231] [LCMS]: 489

[0232] [Synthetic Example 13] Synthesis of Compound A-24

[0233]

[0234] Instead of 2-phenyl-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)benzo[4,5]thieno[3,2-d]pyrimidine used in Synthesis Example 1, 1-phenyl-2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)-1H-benzo[d]imidazole was used, except that the same procedure as in [Synthesis Example 1] was performed to obtain the target compound (7.0 g, yield: 71%).

[0235] [LCMS]: 477

[0236] [Synthetic Example 14] Synthesis of Compound B-1

[0237]

[0238] 4-Chloro-2,9-diethyl-1,10-phenanthroline (5.6 g, 20.6 mmol), 2-phenyl-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)benzo[4,5]thieno[3,2-d]pyrimidine (9.6 g, 20.6 mmol), Pd(OAc)2 (0.2 g, 1.0 mmol), Xphos (1.0 g, 2.1 mmol), and Cs2CO3 (13.5 g, 41.3 mmol) were placed in toluene (50 mL), EtOH (10 mL), and H2O (10 mL) and heated under reflux for 12 hours. After the reaction was complete, the mixture was extracted with dichloromethane and filtered through MgSO4. After removing the solvent from the filtered organic layer, the target compound (9.0 g, yield: 75%) was obtained by column chromatography.

[0239] [LCMS]: 573

[0240] [Synthetic Example 15] Synthesis of Compound B-2

[0241]

[0242] Instead of 2-phenyl-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)benzo[4,5]thieno[3,2-d]pyrimidine used in Synthesis Example 14, 2-phenyl-4-(3-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)benzo[4,5]thieno[3,2-d]pyrimidine was used, except that the same process as in Synthesis Example 14 was performed to obtain the target compound (9.0 g, yield: 75%).

[0243] [LCMS]: 573

[0244] [Synthetic Example 16] Synthesis of Compound B-5

[0245]

[0246] Instead of 2-phenyl-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)benzo[4,5]thieno[3,2-d]pyrimidine, 2-phenyl-4-(3-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)benzofuran[3,2-d]pyrimidine was used, except that the same process as in [Synthetic Example 14] was performed to obtain the target compound (8.6 g, yield: 75%).

[0247] [LCMS]:557

[0248] [Synthetic Example 17] Synthesis of Compound B-7

[0249]

[0250] Instead of 2-phenyl-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)benzo[4,5]thieno[3,2-d]pyrimidine used in Synthesis Example 14, 4-phenyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)benzo[4,5]thieno[3,2-d]pyrimidine was used, and the same procedure as in Synthesis Example 14 was performed to obtain the target compound (8.5 g, yield: 72%).

[0251] [LCMS]: 573

[0252] [Synthetic Example 18] Synthesis of Compound B-8

[0253]

[0254] Instead of 2-phenyl-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)benzo[4,5]thieno[3,2-d]pyrimidine, 4-phenyl-2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)benzo[4,5]thieno[3,2-d]pyrimidine was used, except that the same process as in [Synthetic Example 14] was performed to obtain the target compound (8.5 g, yield: 72%).

[0255] [LCMS]: 573

[0256] [Synthetic Example 19] Synthesis of Compound B-13

[0257]

[0258] Instead of 2-phenyl-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)benzo[4,5]thieno[3,2-d]pyrimidine, 6,8-diphenyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)-[1,2,4]triazolo[1,5-a]pyridine was used, except that the same process as in [Synthetic Example 14] was performed to obtain the target compound (8.6 g, yield: 72%).

[0259] [LCMS]: 582

[0260] [Synthetic Example 20] Synthesis of Compound B-14

[0261]

[0262] Instead of 2-phenyl-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)benzo[4,5]thieno[3,2-d]pyrimidine, 6,8-diphenyl-2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)-[1,2,4]triazolo[1,5-a]pyridine was used, except that the same process as in [Synthetic Example 14] was performed to obtain the target compound (8.6 g, yield: 72%).

[0263] [LCMS]: 582

[0264] [Synthetic Example 21] Synthesis of Compound B-16

[0265]

[0266] Instead of 2-phenyl-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)benzo[4,5]thieno[3,2-d]pyrimidine, 6-phenyl-2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)-[1,2,4]triazolo[1,5-a]pyridine was used, except that the same process as in [Synthetic Example 14] was performed to obtain the target compound (7.5 g, yield: 71%).

[0267] [LCMS]: 506

[0268] [Synthesis Example 22] Synthesis of Compound B-17

[0269]

[0270] Instead of 2-phenyl-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)benzo[4,5]thieno[3,2-d]pyrimidine, 8-phenyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)-[1,2,4]triazolo[1,5-a]pyridine was used, except that the same process as in [Synthetic Example 14] was performed to obtain the target compound (7.5 g, yield: 71%).

[0271] [LCMS]: 506

[0272] [Synthetic Example 23] Synthesis of Compound B-19

[0273]

[0274] Instead of 2-phenyl-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)benzo[4,5]thieno[3,2-d]pyrimidine used in Synthesis Example 14, 2,3,5-triphenyl-6-(4-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)pyrazine was used, except that the same process as in [Synthesis Example 14] was performed to obtain the target compound (9.2 g, yield: 72%).

[0275] [LCMS]: 619

[0276] [Synthesis Example 24] Synthesis of Compound B-20

[0277]

[0278] Instead of 2-phenyl-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)benzo[4,5]thieno[3,2-d]pyrimidine used in Synthesis Example 14, 2,3,5-triphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)pyrazine was used, except that the same process as in [Synthesis Example 14] was performed to obtain the target compound (9.2 g, yield: 72%).

[0279] [LCMS]: 619

[0280] [Synthesis Example 25] Synthesis of Compound B-22

[0281]

[0282] Instead of 2-phenyl-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)benzo[4,5]thieno[3,2-d]pyrimidine used in Synthesis Example 14, 4-phenyl-2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)quinazoline was used, except that the same process as in [Synthesis Example 14] was performed to obtain the target compound (7.5 g, yield: 70%).

[0283] [LCMS]: 517

[0284] [Synthesis Example 26] Synthesis of Compound B-24

[0285]

[0286] Instead of 2-phenyl-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)benzo[4,5]thieno[3,2-d]pyrimidine used in Synthesis Example 14, 1-phenyl-2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)-1H-benzo[d]imidazole was used, except that the same process as in [Synthesis Example 14] was performed to obtain the target compound (7.7 g, yield: 74%).

[0287] [LCMS]: 505

[0288] [Synthesis Example 27] Synthesis of Compound C-1

[0289]

[0290] 4-Chloro-2,9-diisopropyl-1,10-phenanthroline (6.15 g, 20.6 mmol), 2-phenyl-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)benzo[4,5]thieno[3,2-d]pyrimidine (9.6 g, 20.6 mmol), Pd(OAc)2 (0.2 g, 1.0 mmol), Xphos (1.0 g, 2.1 mmol), and Cs2CO3 (13.5 g, 41.3 mmol) were placed in toluene (50 mL), EtOH (10 mL), and H2O (10 mL) and heated under reflux for 12 hours. After the reaction was complete, the mixture was extracted with dichloromethane and filtered through MgSO4. After removing the solvent from the filtered organic layer, the target compound (9.7 g, yield: 78%) was obtained by column chromatography.

[0291] [LCMS]: 601

[0292] [Synthesis Example 28] Synthesis of Compound C-2

[0293]

[0294] Instead of 2-phenyl-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)benzo[4,5]thieno[3,2-d]pyrimidine used in Synthesis Example 27, 2-phenyl-4-(3-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)benzo[4,5]thieno[3,2-d]pyrimidine was used, except that the same process as in Synthesis Example 27 was performed to obtain the target compound (9.7 g, yield: 78%).

[0295] [LCMS]: 601

[0296] [Synthesis Example 29] Synthesis of Compound C-5

[0297]

[0298] Instead of 2-phenyl-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)benzo[4,5]thieno[3,2-d]pyrimidine used in Synthesis Example 27, 2-phenyl-4-(3-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)benzofuran[3,2-d]pyrimidine was used, except that the same process as in [Synthesis Example 27] was performed to obtain the target compound (9.0 g, yield: 75%).

[0299] [LCMS]: 585

[0300] [Synthesis Example 30] Synthesis of Compound C-7

[0301]

[0302] Instead of 2-phenyl-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)benzo[4,5]thieno[3,2-d]pyrimidine used in Synthesis Example 27, 4-phenyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)benzo[4,5]thieno[3,2-d]pyrimidine was used, and the same procedure as in Synthesis Example 27 was performed to obtain the target compound (9.7 g, yield: 78%).

[0303] [LCMS]: 601

[0304] [Synthesis Example 31] Synthesis of Compound C-8

[0305]

[0306] Instead of 2-phenyl-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)benzo[4,5]thieno[3,2-d]pyrimidine used in Synthesis Example 27, 4-phenyl-2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)benzo[4,5]thieno[3,2-d]pyrimidine was used, and the same procedure as in Synthesis Example 27 was performed to obtain the target compound (9.7 g, yield: 78%).

[0307] [LCMS]: 601

[0308] [Synthesis Example 32] Synthesis of Compound C-13

[0309]

[0310] Instead of 2-phenyl-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)benzo[4,5]thieno[3,2-d]pyrimidine, 6,8-diphenyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)-[1,2,4]triazolo[1,5-a]pyridine was used, except that the same process as in [Synthetic Example 27] was performed to obtain the target compound (8.8 g, yield: 70%).

[0311] [LCMS]: 610

[0312] [Synthesis Example 33] Synthesis of Compound C-14

[0313]

[0314] Instead of 2-phenyl-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)benzo[4,5]thieno[3,2-d]pyrimidine, 6,8-diphenyl-2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)-[1,2,4]triazolo[1,5-a]pyridine was used, except that the same process as in [Synthetic Example 27] was performed to obtain the target compound (8.8 g, yield: 70%).

[0315] [LCMS]: 610

[0316] [Synthesis Example 34] Synthesis of Compound C-16

[0317]

[0318] Instead of 2-phenyl-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)benzo[4,5]thieno[3,2-d]pyrimidine used in Synthesis Example 27, 6-phenyl-2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)-[1,2,4]triazolo[1,5-a]pyridine was used, except that the same process as in [Synthesis Example 27] was performed to obtain the target compound (7.4 g, yield: 67%).

[0319] [LCMS]: 534

[0320] [Synthesis Example 35] Synthesis of Compound C-17

[0321]

[0322] Instead of 2-phenyl-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)benzo[4,5]thieno[3,2-d]pyrimidine used in Synthesis Example 27, 8-phenyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)-[1,2,4]triazolo[1,5-a]pyridine was used, except that the same process as in [Synthesis Example 27] was performed to obtain the target compound (7.4 g, yield: 67%).

[0323] [LCMS]: 534

[0324] [Synthesis Example 36] Synthesis of Compound C-19

[0325]

[0326] Instead of 2-phenyl-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)benzo[4,5]thieno[3,2-d]pyrimidine used in Synthesis Example 27, 2,3,5-triphenyl-6-(4-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)pyrazine was used, except that the same process as in [Synthesis Example 27] was performed to obtain the target compound (8.6 g, yield: 65%).

[0327] [LCMS]: 647

[0328] [Synthesis Example 37] Synthesis of Compound C-20

[0329]

[0330] Instead of 2-phenyl-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)benzo[4,5]thieno[3,2-d]pyrimidine used in Synthesis Example 27, 2,3,5-triphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)pyrazine was used, except that the same process as in [Synthesis Example 27] was performed to obtain the target compound (8.6 g, yield: 65%).

[0331] [LCMS]: 647

[0332] [Synthesis Example 38] Synthesis of Compound C-22

[0333]

[0334] Instead of 2-phenyl-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)benzo[4,5]thieno[3,2-d]pyrimidine used in Synthesis Example 27, 4-phenyl-2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)quinazoline was used, except that the same process as in [Synthesis Example 27] was performed to obtain the target compound (7.1 g, yield: 63%).

[0335] [LCMS]: 545

[0336] [Synthesis Example 39] Synthesis of Compound C-24

[0337]

[0338] Instead of 2-phenyl-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)benzo[4,5]thieno[3,2-d]pyrimidine used in Synthesis Example 27, 1-phenyl-2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)-1H-benzo[d]imidazole was used, except that the same process as in [Synthesis Example 27] was performed to obtain the target compound (7.1 g, yield: 65%).

[0339] [LCMS]: 533

[0340] [Synthetic Example 40] Synthesis of Compound D-1

[0341]

[0342] 2,9-Di-tert-butyl-4-chloro-1,10-phenanthroline (6.75 g, 20.6 mmol), 2-phenyl-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)benzo[4,5]thieno[3,2-d]pyrimidine (9.6 g, 20.6 mmol), Pd(OAc)2 (0.2 g, 1.0 mmol), Xphos (1.0 g, 2.1 mmol), and Cs2CO3 (13.5 g, 41.3 mmol) were placed in toluene (50 mL), EtOH (10 mL), and H2O (10 mL) and heated under reflux for 12 hours. After the reaction was complete, the mixture was extracted with dichloromethane and filtered through MgSO4. After removing the solvent from the filtered organic layer, the target compound (8.3 g, yield: 64%) was obtained by column chromatography.

[0343] [LCMS]:629

[0344] [Synthetic Example 41] Synthesis of Compound D-2

[0345]

[0346] Instead of 2-phenyl-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)benzo[4,5]thieno[3,2-d]pyrimidine used in Synthesis Example 40, 2-phenyl-4-(3-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)benzo[4,5]thieno[3,2-d]pyrimidine was used, except that the same process as in Synthesis Example 40 was performed to obtain the target compound (8.3 g, yield: 64%).

[0347] [LCMS]:629

[0348] [Synthetic Example 42] Synthesis of Compound D-5

[0349]

[0350] Instead of 2-phenyl-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)benzo[4,5]thieno[3,2-d]pyrimidine used in Synthesis Example 40, 2-phenyl-4-(3-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)benzofuran[3,2-d]pyrimidine was used, except that the same process as in [Synthesis Example 40] was performed to obtain the target compound (8.1 g, yield: 64%).

[0351] [LCMS]: 613

[0352] [Synthetic Example 43] Synthesis of Compound D-7

[0353]

[0354] Instead of 2-phenyl-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)benzo[4,5]thieno[3,2-d]pyrimidine used in Synthesis Example 40, 4-phenyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)benzo[4,5]thieno[3,2-d]pyrimidine was used, except that the same process as in Synthesis Example 40 was performed to obtain the target compound (8.3 g, yield: 64%).

[0355] [LCMS]:629

[0356] [Synthetic Example 44] Synthesis of Compound D-8

[0357]

[0358] Instead of 2-phenyl-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)benzo[4,5]thieno[3,2-d]pyrimidine used in Synthesis Example 40, 4-phenyl-2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)benzo[4,5]thieno[3,2-d]pyrimidine was used, except that the same process as in Synthesis Example 40 was performed to obtain the target compound (8.3 g, yield: 64%).

[0359] [LCMS]:629

[0360] [Synthetic Example 45] Synthesis of Compound D-13

[0361]

[0362] Instead of 2-phenyl-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)benzo[4,5]thieno[3,2-d]pyrimidine used in Synthesis Example 40, 6,8-diphenyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)-[1,2,4]triazolo[1,5-a]pyridine was used, except that the same process as in [Synthesis Example 40] was performed to obtain the target compound (8.0 g, yield: 61%).

[0363] [LCMS]: 638

[0364] [Synthetic Example 46] Synthesis of Compound D-14

[0365]

[0366] Instead of 2-phenyl-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)benzo[4,5]thieno[3,2-d]pyrimidine, 6,8-diphenyl-2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)-[1,2,4]triazolo[1,5-a]pyridine was used, except that the same process as in [Synthetic Example 40] was performed to obtain the target compound (8.0 g, yield: 61%).

[0367] [LCMS]: 638

[0368] [Synthetic Example 47] Synthesis of Compound D-16

[0369]

[0370] Instead of 2-phenyl-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)benzo[4,5]thieno[3,2-d]pyrimidine used in Synthesis Example 40, 6-phenyl-2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)-[1,2,4]triazolo[1,5-a]pyridine was used, except that the same process as in [Synthesis Example 40] was performed to obtain the target compound (7.2 g, yield: 62%).

[0371] [LCMS]:562

[0372] [Synthetic Example 48] Synthesis of Compound D-17

[0373]

[0374] Instead of 2-phenyl-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)benzo[4,5]thieno[3,2-d]pyrimidine used in Synthesis Example 40, 8-phenyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)-[1,2,4]triazolo[1,5-a]pyridine was used, except that the same process as in [Synthesis Example 40] was performed to obtain the target compound (7.2 g, yield: 62%).

[0375] [LCMS]:562

[0376] [Synthetic Example 49] Synthesis of Compound D-19

[0377]

[0378] Instead of 2-phenyl-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)benzo[4,5]thieno[3,2-d]pyrimidine used in Synthesis Example 40, 2,3,5-triphenyl-6-(4-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)pyrazine was used, except that the same process as in [Synthesis Example 40] was performed to obtain the target compound (8.7 g, yield: 63%).

[0379] [LCMS]: 675

[0380] [Synthesis Example 50] Synthesis of Compound D-20

[0381]

[0382] Instead of 2-phenyl-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)benzo[4,5]thieno[3,2-d]pyrimidine used in Synthesis Example 40, 2,3,5-triphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)pyrazine was used, except that the same process as in [Synthesis Example 40] was performed to obtain the target compound (8.7 g, yield: 63%).

[0383] [LCMS]: 675

[0384] [Synthetic Example 51] Synthesis of Compound D-22

[0385]

[0386] Instead of 2-phenyl-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)benzo[4,5]thieno[3,2-d]pyrimidine used in Synthesis Example 40, 4-phenyl-2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)quinazoline was used, except that the same process as in [Synthesis Example 40] was performed to obtain the target compound (7.1 g, yield: 60%).

[0387] [LCMS]: 573

[0388] [Synthetic Example 52] Synthesis of Compound D-24

[0389]

[0390] Instead of 2-phenyl-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)benzo[4,5]thieno[3,2-d]pyrimidine used in Synthesis Example 40, 1-phenyl-2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)-1H-benzo[d]imidazole was used, except that the same process as in [Synthesis Example 40] was performed to obtain the target compound (7.0 g, yield: 60%).

[0391] [LCMS]: 561

[0392] [Synthetic Example 53] Synthesis of Compound E-1

[0393]

[0394] 4-Chloro-2-ethyl-9-methyl-1,10-phenanthroline (5.3 g, 20.6 mmol), 2-phenyl-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)benzo[4,5]thieno[3,2-d]pyrimidine (9.6 g, 20.6 mmol), Pd(OAc)2 (0.2 g, 1.0 mmol), Xphos (1.0 g, 2.1 mmol), and Cs2CO3 (13.5 g, 41.3 mmol) were placed in toluene (50 mL), EtOH (10 mL), and H2O (10 mL) and heated under reflux for 12 hours. After the reaction was complete, the mixture was extracted with dichloromethane and filtered through MgSO4. After removing the solvent from the filtered organic layer, the target compound (7.6 g, yield: 66%) was obtained by column chromatography.

[0395] [LCMS]:559

[0396] [Synthetic Example 54] Synthesis of Compound E-2

[0397]

[0398] Instead of 2-phenyl-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)benzo[4,5]thieno[3,2-d]pyrimidine, 2-phenyl-4-(3-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)benzo[4,5]thieno[3,2-d]pyrimidine was used, except that the same process as in [Synthetic Example 53] was performed to obtain the target compound (7.6 g, yield: 66%).

[0399] [LCMS]:559

[0400] [Synthetic Example 55] Synthesis of Compound E-5

[0401]

[0402] Instead of 2-phenyl-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)benzo[4,5]thieno[3,2-d]pyrimidine, 2-phenyl-4-(3-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)benzofuran[3,2-d]pyrimidine was used, except that the same process as in [Synthetic Example 53] was performed to obtain the target compound (7.4 g, yield: 66%).

[0403] [LCMS]: 543

[0404] [Synthetic Example 56] Synthesis of Compound E-7

[0405]

[0406] Instead of 2-phenyl-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)benzo[4,5]thieno[3,2-d]pyrimidine, 4-phenyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)benzo[4,5]thieno[3,2-d]pyrimidine was used, except that the same process as in [Synthetic Example 53] was performed to obtain the target compound (7.6 g, yield: 66%).

[0407] [LCMS]:559

[0408] [Synthesis Example 57] Synthesis of Compound E-8

[0409]

[0410] Instead of 2-phenyl-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)benzo[4,5]thieno[3,2-d]pyrimidine, 4-phenyl-2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)benzo[4,5]thieno[3,2-d]pyrimidine was used, except that the same process as in [Synthetic Example 53] was performed to obtain the target compound (7.6 g, yield: 66%).

[0411] [LCMS]:559

[0412] [Synthetic Example 58] Synthesis of Compound E-13

[0413]

[0414] Instead of 2-phenyl-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)benzo[4,5]thieno[3,2-d]pyrimidine, 6,8-diphenyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)-[1,2,4]triazolo[1,5-a]pyridine was used, except that the same process as in [Synthetic Example 53] was performed to obtain the target compound (7.5 g, yield: 64%).

[0415] [LCMS]:568

[0416] [Synthesis Example 59] Synthesis of Compound E-14

[0417]

[0418] Instead of 2-phenyl-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)benzo[4,5]thieno[3,2-d]pyrimidine, 6,8-diphenyl-2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)-[1,2,4]triazolo[1,5-a]pyridine was used, except that the same process as in [Synthetic Example 53] was performed to obtain the target compound (7.5 g, yield: 64%).

[0419] [LCMS]:568

[0420] [Synthetic Example 60] Synthesis of Compound E-16

[0421]

[0422] Instead of 2-phenyl-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)benzo[4,5]thieno[3,2-d]pyrimidine, 6-phenyl-2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)-[1,2,4]triazolo[1,5-a]pyridine was used, except that the same process as in [Synthetic Example 53] was performed to obtain the target compound (6.1 g, yield: 61%).

[0423] [LCMS]: 492

[0424] [Synthetic Example 61] Synthesis of Compound E-17

[0425]

[0426] Instead of 2-phenyl-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)benzo[4,5]thieno[3,2-d]pyrimidine used in Synthesis Example 53, 8-phenyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)-[1,2,4]triazolo[1,5-a]pyridine was used, except that the same process as in [Synthesis Example 53] was performed to obtain the target compound (6.1 g, yield: 61%).

[0427] [LCMS]: 492

[0428] [Synthetic Example 62] Synthesis of Compound E-19

[0429]

[0430] Instead of 2-phenyl-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)benzo[4,5]thieno[3,2-d]pyrimidine used in Synthesis Example 53, 2,3,5-triphenyl-6-(4-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)pyrazine was used, except that the same process as in [Synthesis Example 53] was performed to obtain the target compound (7.5 g, yield: 60%).

[0431] [LCMS]: 605

[0432] [Synthesis Example 63] Synthesis of Compound E-20

[0433]

[0434] Instead of 2-phenyl-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)benzo[4,5]thieno[3,2-d]pyrimidine used in Synthesis Example 53, 2,3,5-triphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)pyrazine was used, except that the same process as in [Synthesis Example 53] was performed to obtain the target compound (7.5 g, yield: 60%).

[0435] [LCMS]: 605

[0436] [Synthesis Example 64] Synthesis of Compound E-22

[0437]

[0438] Instead of 2-phenyl-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)benzo[4,5]thieno[3,2-d]pyrimidine used in Synthesis Example 53, 4-phenyl-2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)quinazoline was used, except that the same process as in [Synthesis Example 53] was performed to obtain the target compound (6.3 g, yield: 61%).

[0439] [LCMS]: 503

[0440] [Synthetic Example 65] Synthesis of Compound E-24

[0441]

[0442] Instead of 2-phenyl-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)benzo[4,5]thieno[3,2-d]pyrimidine used in Synthesis Example 53, 1-phenyl-2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)-1H-benzo[d]imidazole was used, except that the same process as in [Synthesis Example 53] was performed to obtain the target compound (6.3 g, yield: 62%).

[0443] [LCMS]: 491

[0444] [Synthetic Example 66] Synthesis of Compound F-1

[0445]

[0446] 4-Chloro-2-isopropyl-9-methyl-1,10-phenanthroline (5.6 g, 20.6 mmol), 2-phenyl-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaneborane-2-yl)phenyl)benzo[4,5]thieno[3,2-d]pyrimidine (9.6 g, 20.6 mmol), Pd(OAc)2 (0.2 g, 1.0 mmol), Xphos (1.0 g, 2.1 mmol), and Cs2CO3 (13.5 g, 41.3 mmol) were placed in toluene (50 mL), EtOH (10 mL), and H2O (10 mL) and heated under reflux for 12 hours. After the reaction was complete, the mixture was extracted with dichloromethane and filtered through MgSO4. After removing the solvent from the filtered organic layer, the target compound (7.1 g, yield: 60%) was obtained by column chromatography.

[0447] [LCMS]: 573

[0448] [Synthesis Example 67] Synthesis of Compound F-2

[0449]

[0450] Instead of 2-phenyl-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)benzo[4,5]thieno[3,2-d]pyrimidine used in Synthesis Example 66, 2-phenyl-4-(3-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)benzo[4,5]thieno[3,2-d]pyrimidine was used, except that the same process as in Synthesis Example 66 was performed to obtain the target compound (7.1 g, yield: 60%).

[0451] [LCMS]: 573

[0452] [Synthetic Example 68] Synthesis of Compound F-5

[0453]

[0454] Instead of 2-phenyl-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)benzo[4,5]thieno[3,2-d]pyrimidine used in Synthesis Example 66, 2-phenyl-4-(3-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)benzofuran[3,2-d]pyrimidine was used, except that the same process as in [Synthesis Example 66] was performed to obtain the target compound (6.9 g, yield: 60%).

[0455] [LCMS]:529

[0456] [Synthesis Example 69] Synthesis of Compound F-7

[0457]

[0458] Instead of 2-phenyl-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)benzo[4,5]thieno[3,2-d]pyrimidine, 4-phenyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)benzo[4,5]thieno[3,2-d]pyrimidine was used, except that the same process as in [Synthetic Example 66] was performed to obtain the target compound (7.1 g, yield: 60%).

[0459] [LCMS]: 573

[0460] [Synthesis Example 70] Synthesis of Compound F-8

[0461]

[0462] Instead of 2-phenyl-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)benzo[4,5]thieno[3,2-d]pyrimidine used in Synthesis Example 66, 4-phenyl-2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)benzo[4,5]thieno[3,2-d]pyrimidine was used, except that the same process as in Synthesis Example 66 was performed to obtain the target compound (7.1 g, yield: 60%).

[0463] [LCMS]: 573

[0464] [Synthetic Example 71] Synthesis of Compound F-13

[0465]

[0466] Instead of 2-phenyl-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)benzo[4,5]thieno[3,2-d]pyrimidine, 6,8-diphenyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)-[1,2,4]triazolo[1,5-a]pyridine was used, except that the same process as in [Synthetic Example 66] was performed to obtain the target compound (7.1 g, yield: 59%).

[0467] [LCMS]: 582

[0468] [Synthesis Example 72] Synthesis of Compound F-14

[0469]

[0470] Instead of 2-phenyl-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)benzo[4,5]thieno[3,2-d]pyrimidine, 6,8-diphenyl-2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)-[1,2,4]triazolo[1,5-a]pyridine was used, except that the same process as in [Synthetic Example 66] was performed to obtain the target compound (7.1 g, yield: 59%).

[0471] [LCMS]: 582

[0472] [Synthesis Example 73] Synthesis of Compound F-16

[0473]

[0474] Instead of 2-phenyl-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)benzo[4,5]thieno[3,2-d]pyrimidine, 6-phenyl-2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)-[1,2,4]triazolo[1,5-a]pyridine was used, except that the same process as in [Synthetic Example 66] was performed to obtain the target compound (6.1 g, yield: 59%).

[0475] [LCMS]: 506

[0476] [Synthetic Example 74] Synthesis of Compound F-17

[0477]

[0478] Instead of 2-phenyl-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)benzo[4,5]thieno[3,2-d]pyrimidine used in Synthesis Example 66, 8-phenyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)-[1,2,4]triazolo[1,5-a]pyridine was used, except that the same process as in [Synthesis Example 66] was performed to obtain the target compound (6.1 g, yield: 59%).

[0479] [LCMS]: 506

[0480] [Synthetic Example 75] Synthesis of Compound F-19

[0481]

[0482] Instead of 2-phenyl-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)benzo[4,5]thieno[3,2-d]pyrimidine used in Synthesis Example 66, 2,3,5-triphenyl-6-(4-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)pyrazine was used, except that the same process as in [Synthesis Example 66] was performed to obtain the target compound (7.7 g, yield: 60%).

[0483] [LCMS]: 619

[0484] [Synthesis Example 76] Synthesis of Compound F-20

[0485]

[0486] Instead of 2-phenyl-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)benzo[4,5]thieno[3,2-d]pyrimidine used in Synthesis Example 66, 2,3,5-triphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)pyrazine was used, except that the same process as in [Synthesis Example 66] was performed to obtain the target compound (7.7 g, yield: 60%).

[0487] [LCMS]: 619

[0488] [Synthesis Example 77] Synthesis of Compound F-22

[0489]

[0490] Instead of 2-phenyl-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)benzo[4,5]thieno[3,2-d]pyrimidine used in Synthesis Example 66, 4-phenyl-2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)quinazoline was used, except that the same process as in [Synthesis Example 66] was performed to obtain the target compound (6.2 g, yield: 58%).

[0491] [LCMS]: 517

[0492] [Synthesis Example 78] Synthesis of Compound F-24

[0493]

[0494] Instead of 2-phenyl-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)benzo[4,5]thieno[3,2-d]pyrimidine used in Synthesis Example 66, 1-phenyl-2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)-1H-benzo[d]imidazole was used, except that the same process as in [Synthesis Example 66] was performed to obtain the target compound (6.0 g, yield: 58%).

[0495] [LCMS]: 505

[0496] [Example 1] - Fabrication of a blue organic electroluminescent element

[0497] The compound synthesized in Synthesis Example 1 was purified by high-purity sublimation using a commonly known method, and a blue organic electroluminescent element was fabricated as follows.

[0498] First, a glass substrate coated with an indium tin oxide (ITO) film at a thickness of 1500 Å was ultrasonically washed with distilled water. After washing with distilled water, it was ultrasonically washed with solvents such as isopropanol, acetone, and methanol, and then dried. It was then transferred to a UV ozone cleaner (Power sonic 405, Hwashintech), where it was cleaned with UV light for 5 minutes before being transferred to a vacuum evaporation machine.

[0499] An organic electroluminescent element was fabricated on an ITO transparent electrode prepared as described above, in the following order: DS-205 (Doosan Electron Co., Ltd., 80 nm) / NPB (15 nm) / ADN + 5% DS-405 (Doosan Electron Co., Ltd., 30 nm) / compound A-1 (30 nm) / LiF (1 nm) / Al (200 nm). The structures of the NPB and ADN used are as follows.

[0500]

[0501] [Examples 2 to 78]

[0502] Instead of compound A-1 used as the electron transport layer material in Example 1, the compounds listed in Table 1 below were used, and the same procedure as in Example 1 was followed to fabricate a blue organic electroluminescent element.

[0503] [Comparative Examples 1 to 8] - Fabrication of Blue Organic Electroluminescent Element

[0504] Instead of compound A-1 used as the electron transport layer material in Example 1, compounds A to H were used respectively, and the same procedure as in Example 1 was followed to fabricate a blue organic electroluminescent element.

[0505]

[0506] [Evaluation Example 1]

[0507] For the blue organic electroluminescent devices prepared in Examples 1 to 78 and Comparative Examples 1 to 8, the current density was measured to be 10 mA / cm². 2 The driving voltage, current efficiency, and emission wavelength at that time are shown in Table 1 below.

[0508] [Table 1]

[0509]

[0510]

[0511]

[0512] As shown in Table 1 above, the blue organic light-emitting diodes (OLEDs) with electron transport layers containing compounds of the present invention having alkyl-substituted phenanthroline moieties at positions 2 and 9 (Examples 1 to 78) showed improved driving voltage and efficiency compared to OLEDs with electron transport layers containing compounds having unsubstituted alkyl-substituted phenanthroline moieties (Comparative Examples 1-2) and OLEDs with electron transport layers containing compounds having substituted aryl phenanthroline moieties (Comparative Examples 3-4). Furthermore, the compounds of the present invention used in Examples 1-78 exhibited lower sublimation temperatures during device fabrication compared to compounds containing substituted aryl phenanthroline moieties (Compounds C and D), thus preventing device degradation.

[0513] Furthermore, the compounds of the present invention containing phenanthroline moieties with alkyl substitutions at positions 2 and 9 exhibit improved component properties compared to compounds containing phenanthroline moieties with alkyl substitutions at other positions. On the other hand, the components of Comparative Example 5 (compound E) containing phenanthroline moieties with alkyl substitutions at positions 2 and 8, and Comparative Example 6 (compound F) containing phenanthroline moieties with alkyl substitutions at positions 2 and 6, compared to Comparative Examples 1 to 4 (compounds A to D) containing unsubstituted or aryl-substituted phenanthroline moieties, showed slightly improved efficiency characteristics, but the component properties were not significantly improved because the inherent active sites of phenanthroline were not blocked. Therefore, it can be confirmed that even compounds containing alkyl-substituted phenanthroline derivatives can only maintain stability when alkyl substitutions are present at positions 2 and 9 of the active site.

[0514] Furthermore, compared to Comparative Examples 7-8, which utilize phenanthroline moieties containing alkyl groups at positions 2 and 9 and heteroaryl groups (e.g., EWG) at position 4, the devices using compounds of the present invention exhibit lower driving voltages and higher luminous efficiency than those using compounds containing phenanthroline moieties containing alkyl groups at positions 2 and 9 and heteroaryl groups at positions other than 4 (e.g., positions 3 or 5). This demonstrates that even in compounds having phenanthroline moieties with alkyl groups substituted at positions 2 and 9, the position of the electron-withdrawing group (EWG) significantly affects the device characteristics.

[0515] [Example 79] - Fabrication of Organic Electroluminescent Element

[0516] The compound A-1 synthesized in Synthesis Example 1 was purified to high purity by sublimation using a commonly known method, and a blue organic electroluminescent element was prepared as follows.

[0517] First, a glass substrate coated with an indium tin oxide (ITO) film at a thickness of 1500 Å was ultrasonically cleaned with distilled water. After distilled water cleaning, it was ultrasonically cleaned with solvents such as isopropanol, acetone, and methanol, and then dried. It was then transferred to a UV ozone cleaner (Power sonic 405, Hwashintech), where it was cleaned with UV light for 5 minutes before being transferred to a vacuum evaporation machine.

[0518] An organic electroluminescent element was fabricated on the ITO transparent electrode prepared as described above by stacking DS-205 (Doosan Electronics Co., Ltd., 80nm) / NPB (15nm) / ADN + 5% DS-405 (Doosan Electronics Co., Ltd., 30nm) / Alq3 (30nm) / Compound A-1 (15nm) / DS-505 (Doosan Electronics Co., Ltd., 15nm) / NPB (15nm) / CBP + 10% (piq)2Ir(acac) (40nm) / Alq3 (30nm) / LiF (1nm) / Al (200nm). Furthermore, the structures of the NPB and ADN used were the same as those described in Example 1, and the structures of Alq3, CBP, and (piq)2Ir(acac) are as follows.

[0519]

[0520] [Examples 80 to 156]

[0521] Instead of compound A-1 used as the N-type charge generation layer material in Example 79, the compounds listed in Table 2 below were used, and the organic electroluminescent element was fabricated in the same manner as in Example 79.

[0522] [Comparative Examples 9 to 16] - Fabrication of Organic Electroluminescent Devices

[0523] Instead of compound A-1 used as the N-type charge-generating layer material in Example 79, compounds A to H were used, and the organic electroluminescent element was fabricated in the same manner as in Example 79. In this case, compounds A to H are the same as those described in Comparative Examples 1 to 8, and therefore are omitted.

[0524] [Evaluation Example 2]

[0525] For the organic electroluminescent devices fabricated in Examples 79 to 156 and Comparative Examples 9 to 16, respectively, a current density of 10 mA / cm² was measured. 2The driving voltage and current efficiency at that time are shown in Table 2 below.

[0526] [Table 2]

[0527]

[0528]

[0529]

[0530] As shown in Table 2 above, the blue organic electroluminescent elements (Examples 79-156) using compounds containing alkyl-substituted phenanthroline moieties at positions 2 and 9 in the N-type charge generation layer showed improved driving voltage and efficiency compared to organic electroluminescent elements (Comparative Examples 9-10) using compounds containing unsubstituted alkyl-substituted phenanthroline moieties and organic electroluminescent elements (Comparative Examples 11-12) using compounds containing aryl-substituted phenanthroline moieties. Furthermore, the compounds of the present invention used in the elements of Examples 79-156 exhibited lower sublimation temperatures during element fabrication compared to compounds containing aryl-substituted phenanthroline moieties (Compounds C and D), thus preventing element degradation.

[0531] Furthermore, the components of Examples 79-156, which utilize compounds of the present invention containing alkyl-substituted phenanthroline moieties at positions 2 and 9 as N-type charge-generating layer materials, exhibit superior performance in terms of driving voltage and current efficiency compared to the components of Comparative Examples 13-14, which utilize compounds containing alkyl-substituted phenanthroline moieties at other positions. On the other hand, the components of Comparative Example 13 (compound E), which utilize compounds containing alkyl-substituted phenanthroline moieties at positions 2 and 8 (i.e., compound E), and Comparative Example 14 (compound F), which utilize compounds containing alkyl-substituted phenanthroline moieties at positions 2 and 6 (i.e., compound F), show slightly improved efficiency characteristics compared to the components of Comparative Examples 9-12, which utilize compounds containing unsubstituted or aryl-substituted phenanthroline moieties. However, because the inherent active sites of phenanthroline are not blocked, the characteristics of the components are not significantly improved. Therefore, it can be confirmed that even compounds containing phenanthroline derivatives with introduced alkyl groups can only maintain thermal stability if the active site has alkyl groups substituted at positions 2 and 9.

[0532] Furthermore, the devices of Examples 79-156, which utilize the compounds of the present invention containing phenanthroline moieties with alkyl groups at positions 2 and 9 and an aryl group at position 4, exhibit lower driving voltages and higher luminous efficiency compared to the devices of Comparative Examples 15-16, which utilize phenanthroline moieties containing alkyl groups at positions 2 and 9 and an aryl group at positions other than position 4 (e.g., position 3 or 5). This demonstrates that even in compounds having phenanthroline moieties with alkyl groups substituted at positions 2 and 9, the position of the aryl group significantly affects the device characteristics.

Claims

1. An organic compound represented by the following chemical formula 1: [Chemical Formula 1] In the chemical formula 1, R1 and R2 may be the same or different from each other, and each can be independently denoted as C1~C2. 60 alkyl groups, L1 is C6~C 60 Alpha-aryl, Ar1 is a substituent selected from any of the following chemical formulas: SS1, SS3, SS5, SS6, SS7, and SS9. Among the chemical formulas SS1, SS3, SS5, SS6, SS7, and SS9, Y1 is either S or O. Ar7, Ar8 and Ar 12 Each independently is C6~C 60 Aryl, a is an integer from 0 to 4. Multiple R3s may be the same or different from each other. R3 is independently selected as either hydrogen or C6~C. 60 Aryl groups.

2. The organic compound according to claim 1, wherein the organic compound represented by chemical formula 1 is represented by any one of the following chemical formulas 2 to 5: [Chemical Formula 2] [Chemical Formula 3] [Chemical Formula 4] [Chemical Formula 5] Among the chemical formulas 2 to 5, L1 and Ar1 are the same as defined in claim 1. R2 is a C1~C6 alkyl group.

3. The organic compound according to claim 1, wherein R1 and R2 are the same and are C1-C6 alkyl groups.

4. The organic compound according to claim 1, wherein L1 is a linking group represented by the following chemical formula L: [Chemical formula L] In the chemical formula L, n is an integer from 0 to 3. a is an integer from 0 to 4. When there are multiple R3s, they may be the same as or different from each other. R3 is selected from hydrogen, deuterium, halogen group, hydroxyl group, cyano group, nitro group, amino group, amido group, hydrazine group, hydrazone group, C1~C1 group. 60 Alkyl groups, C2~C 60 alkenyl, C2~C 60 alkynyl group, C3~C 60 Cycloalkyl groups, heterocyclic alkyl groups with 3 to 60 nuclei, C3~C 60 Cycloalkenyl groups, heterocyclic alkenyl groups with 3 to 60 nuclei, C6~C 60 aryl groups, heteroaryl groups with 5 to 60 nuclei, C1~C 60 alkoxy groups, C6~C 60 aryloxy groups, C1~C 60 alkylsilyl, C6~C 60 arylsilyl, C1~C 40 alkylboron group, C6~C 60 arylboryl group, C6~C 60 arylphosphine, C6~C 60 arylphosphine oxide and C6~C 60 It is a group composed of aryl amino groups.

5. The organic compound according to claim 1, wherein L1 is any one of the following linking groups L1 to L4: 。 6. The organic compound according to claim 1, wherein the compound represented by chemical formula 1 is selected from the group consisting of compounds A-1 to A-22, A-24, B-1 to B-22, B-24, C-1 to C-22, C-24, D-1 to D-22, D-24, E-1 to E-22, E-24 and F-1 to F-22, F-24: 。 7. An organic electroluminescent element comprising an anode, a cathode, and one or more organic layers between the anode and the cathode. At least one of the more than one organic layers comprises the organic compound according to any one of claims 1 to 6.

8. The organic electroluminescent element according to claim 7, wherein the organic layer containing the organic compound is an electron transport layer.

9. An organic electroluminescent element comprising: Anodes and cathodes arranged apart from each other; Multiple light-emitting units located between the anode and cathode; and Between adjacent light-emitting units are N-type charge generation layers and P-type charge generation layers. Each of the plurality of light-emitting units comprises a hole transport layer, a light-emitting layer, and an electron transport layer. The N-type charge-generating layer comprises an organic compound according to any one of claims 1 to 6.

10. The organic electroluminescent element according to claim 9, wherein the N-type charge generation layer comprises a host having electron transport properties. The subject is an organic compound as described in any one of claims 1 to 6.

11. The organic electroluminescent device according to claim 10, wherein the N-type charge generation layer further comprises an N-type dopant.

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