Compound and organic electroluminescent element using the same

Abstract

The present application relates to a novel compound and an organic electroluminescent element using the same, in more detail, to an organic compound having excellent electron-transporting ability, heat resistance, carrier-transporting ability, light-emitting ability, and the like, and an organic electroluminescent element in which the light-emitting efficiency, driving voltage, lifespan, and the like are improved by adding the same to one or more organic layers.

Description

Technical Field

[0001] This invention relates to a novel compound and an organic electroluminescent element utilizing the same, and more specifically, to a compound with excellent electron transport capabilities and an organic electroluminescent element whose luminous efficiency, driving voltage, lifetime, and other characteristics are improved by adding the compound to 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 into the organic layer, 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] Luminescent materials can be classified according to their emission color into blue, green, and red luminescent materials, as well as yellow and orange luminescent materials used to produce more natural colors. Furthermore, to increase luminescent efficiency through increased color purity and energy transfer, a host / dopant system can be used as a luminescent material.

[0004] Dopant materials can be divided 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 phosphorescent materials can theoretically improve luminescence efficiency by up to four times compared to fluorescence, research is being vigorously pursued not only on phosphorescent dopants but also on phosphorescent host materials.

[0005] To date, NPB, BCP, and Alq3 are widely known as hole injection layers, hole transport layers, hole blocking layers, and electron transport layers, while anthracene derivatives have been reported as luminescent layer materials. In particular, metal coordination compounds containing Ir, such as Firmic, Ir(ppy)3, and (acac)Ir(btp)2, which offer advantages in efficiency improvement for luminescent layer materials, have been used as phosphorescent dopants for blue, green, and red luminescence. 4,4-dicarbazolybiphenyl (CBP) has been used as a host phosphorescent material.

[0006] However, while conventional organic layer materials offer advantages in terms of luminescence properties, their low glass transition temperature and poor thermal stability prevent them from achieving satisfactory lifetimes in organic electroluminescent devices. Therefore, there is a need to develop high-performance organic layer materials. Summary of the Invention

[0007] Technical issues

[0008] The present invention aims to provide a novel compound that possesses excellent electron injection and transport capabilities, thermal stability, carrier transport capabilities, and luminescence capabilities, and can be used as an organic layer material for organic electroluminescent elements. Specifically, it can be used as a light-emitting layer material, a lifetime improvement layer material, a light-emitting auxiliary layer material, an electron transport layer material, or an electron transport auxiliary layer material. More specifically, it can be used as an electron transport layer material or an electron transport auxiliary layer material.

[0009] Furthermore, the present invention aims to provide an organic electroluminescent element that, by including the aforementioned novel compound, exhibits low driving voltage, high luminous efficiency, excellent electrical stability, and improved lifetime.

[0010] Methods for solving problems

[0011] To achieve the above objectives, the present invention provides compounds represented by the following chemical formula 1:

[0012] [Chemical Formula 1]

[0013]

[0014] (In the above chemical formula 1,

[0015] X1 to X4 may be the same as or different from each other, and each is independently N or C(Ar1), wherein at least two of X1 to X4 are N;

[0016] Y1 is selected from the group consisting of O, S, Se, C(Ar2)(Ar3) and N(Ar4).

[0017] a is 1 or 2.

[0018] b is an integer from 0 to 4.

[0019] R1, R2, and Ar1 to Ar4 may be the same as or different from each other, and are each independently selected from hydrogen, deuterium (D), halogen group, cyano group, nitro group, amino group, hydroxyl group, C1~C4. 40 Alkyl groups, C2~C 40 alkenyl, C2~C 40 alkynyl group, C3~C 40 Cycloalkyl groups, heterocyclic alkyl groups with 3 to 40 nuclei, C6~C 60 aryl, heteroaryl with 5 to 60 nuclei, C1~C 40 alkoxy groups, C6~C 60 aryloxy groups, C1~C 40 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;

[0020] n is an integer from 1 to 4.

[0021] L1 is C6~C 18 Alpha-aryl,

[0022] The alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, alkoxy, aryloxy, alkylsilyl, arylsilyl, alkylboryl, arylboryl, arylphosphinyl, arylphosphine oxide, and arylamino groups of R1, R2, and Ar1 to Ar4, as well as the arylene group of L1, are each independently selected from deuterium (D), halogen, cyano, nitro, amino, hydroxyl, C1~C4. 40 Alkyl groups, C2~C 40 alkenyl, C2~C 40 alkynyl group, C3~C 40 Cycloalkyl groups, heterocyclic alkyl groups with 3 to 40 nuclei, C6~C 60 aryl groups, heteroaryl groups with 5 to 60 nuclei, C1~C 40 alkoxy groups, C6~C 60 aryloxy groups, C1~C 40 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.

[0023] In addition, 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 a compound represented by the above chemical formula 1.

[0024] According to one example, the organic layer containing the above-mentioned compound can be an electron transport layer or an electron transport auxiliary layer.

[0025] Invention Effects

[0026] The compounds of the present invention exhibit excellent electron transport capabilities, electrochemical stability, and thermal stability, and therefore can be used as organic layer materials for organic electroluminescent elements. In particular, when the compounds of the present invention are used as electron transport layer materials or electron transport auxiliary layer materials, compared with conventional materials, organic electroluminescent elements with excellent luminescence performance, low driving voltage, high efficiency, and long lifetime characteristics can be manufactured, and further, full-color display panels with improved performance and lifetime can also be manufactured.

[0027] The effects of the present invention are not limited to the examples described above, and this specification includes a wider variety of effects. Attached Figure Description

[0028] Figure 1 This is a schematic cross-sectional view of an organic electroluminescent element according to a first embodiment of the present invention.

[0029] Figure 2 This is a schematic cross-sectional view of an organic electroluminescent element according to a second embodiment of the present invention.

[0030] Figure 3 This is a schematic cross-sectional view of an organic electroluminescent element according to a third embodiment of the present invention.

[0031] <Explanation of Figure Markers>

[0032] 100: Anode, 200: Cathode

[0033] 300: Organic layer; 310: Hole injection layer.

[0034] 320: Hole transport layer, 330: Emissive layer

[0035] 340: Electron transport layer; 350: Electron injection layer.

[0036] 360: Electronic transmission auxiliary layer. Detailed Implementation

[0037] The present invention will now be described.

[0038] <Novel Organic Compounds>

[0039] The compounds of the present invention, represented by the above-described chemical formula 1, have the following basic structure: a condensed heteroaromatic ring moiety comprising a monocyclic nitrogen-containing heteroaromatic ring fused with a benzo[a] ring, and a spiro[cyclohexane-1,9'-fluorene]moiety bonded to the condensed heteroaromatic ring moiety by a linking group (e.g., an arylene group), wherein a cyano group (-CN) is introduced into one benzene ring of the spiro[cyclohexane-1,9'-fluorene]moiety. The compounds of the present invention, represented by such chemical formula 1, exhibit excellent electron injection and transport capabilities, electrochemical stability, and heat resistance, and can therefore be used as electron transport layer materials or electron transport auxiliary layer materials capable of improving the efficiency, long lifetime, and driving voltage characteristics of organic electroluminescent devices.

[0040] In the compounds of this invention, the condensed heteroaromatic ring moiety is formed by the condensation of a monocyclic nitrogen-containing heteroaromatic ring and a benzo[a] ring. Structurally, it is an electron-withdrawing group (EWG), thus improving electron injection and transport characteristics. Because this condensed heteroaromatic ring moiety has a wider conjugation region compared to monocyclic azazine groups (e.g., pyridyl, pyrimidinyl, triazine) or quinolinyl groups, more electrons can be distributed within the condensed heteroaromatic ring moiety, resulting in excellent initial drive voltage and overall charge transport in the compounds of this invention. Furthermore, since the ET region of the condensed heteroaromatic ring moiety is expanded compared to monocyclic azazine or quinolinyl groups, the compounds of this invention exhibit superior electrical properties in a wider and flatter region, resulting in higher ET power (electronic power), thereby achieving low drive voltage and high efficiency in the device. Here, regarding ET (Electronic Power), the flatter the compound structure, the smoother the intramolecular electron migration, and the higher the electron mobility, thus facilitating electron injection. Furthermore, as strong EWGs are substituted, the LUMO (Low Lumen Mobility) decreases, making it easier for electrons to transition to adjacent energy levels. And as ET power increases, the LUMO decreases further, making electron migration even easier. Therefore, the compounds of this invention, due to the structural stability provided by their flat structure, ensure long-lifetime characteristics of the device. In particular, by incorporating the spiro[cyclohexane-1,9'-fluorene] moiety into the condensed heteroaromatic ring moiety, this invention maximizes the lifetime characteristics of the device, thereby exhibiting advantages in devices with large surface areas.

[0041] Furthermore, in the compounds of the present invention, the condensed heteroaromatic ring moiety has relatively more electrons compared to the conventional dibenzofuranyl or dibenzothiophene group, thus acting as an electron loading gate (EWG), thereby improving the electron injection and transport characteristics of the compounds. Therefore, when the compounds of the present invention are used as electron transport layers or electron transport auxiliary layers in organic electroluminescent devices, not only can the driving voltage of the device be improved, but also the current efficiency of the device can be improved.

[0042] Furthermore, in the compounds of the present invention, the dipole moment is increased by designing a structure in which a cyano group (-CN) is substituted on one of the benzene rings of the spiro[cyclohexane-1,9'-fluorene] moiety. This enhances the interaction with adjacent cathodes, allowing for the acquisition of more electrons from the cathode and their transport to the light-emitting layer, and also improves initial electron generation. Therefore, the compounds of the present invention can improve the initial driving voltage and luminous efficiency of the device. Additionally, the increased dipole moment due to the substituted cyano group in the compounds of the present invention increases the deposition between the electrode and the organic material, thereby minimizing defects within the device.

[0043] In addition, in the compounds of the present invention, the condensed heteroaromatic ring moiety and the spiro[cyclohexane-1,9'-fluorene] moiety are linked by an arylene group (e.g., a monocyclic arylene or a condensed or non-condensed 2-4 cyclic arylene). Therefore, the spiro[cyclohexane-1,9'-fluorene] moiety, as a highly electron-donating group (EDG), and the condensed heteroaromatic ring moiety, as a highly electron-withdrawing group (EWG), are structurally separated, thereby exhibiting a LUMO-HOMO orbital separation effect and improving the bandgap. Thus, the compounds of the present invention can possess appropriate LUMO energies. Therefore, compared to compounds in which the condensed heteroaromatic ring moiety and the spiro[cyclohexane-1,9'-fluorene] moiety are directly linked without a linking group, the compounds of the present invention can further reduce the driving voltage of the device and further improve current efficiency. In addition, the compounds of the present invention have thermal stability, high glass transition temperature characteristics and uniform morphology, thereby improving the properties of the device.

[0044] Furthermore, the compound represented by Chemical Formula 1 of this invention possesses a high triplet energy, thus preventing excitons generated in the emissive layer from diffusing (migrating) to adjacent electron transport layers or hole transport layers. Therefore, the number of excitons contributing to luminescence in the emissive layer can be increased, improving the luminous efficiency of the device, and the device's durability and stability can be enhanced, effectively increasing its lifetime. Since most of the developed materials can be driven at low voltages, they exhibit the resulting improved lifetime physical characteristics.

[0045] As described above, the compounds represented by Chemical Formula 1 of the present invention exhibit excellent electron transport capability, thermal stability, and electrochemical stability. Therefore, the compounds of the present invention can be used as organic layer materials for organic electroluminescent elements, preferably as luminescent layer materials (blue, green, and / or red phosphorescent host materials), electron transport layer / injection layer materials, hole transport layer / injection layer materials, luminescent auxiliary layer materials, lifetime improvement layer materials, and electron transport auxiliary layer materials; more preferably, they can be used as electron transport layer materials and electron transport auxiliary layer materials. The performance and lifetime characteristics of organic electroluminescent elements containing such compounds of the present invention can be significantly improved, and the performance of full-color organic light-emitting panels using such organic electroluminescent elements can be maximized.

[0046] The compound represented by chemical formula 1 of the present invention has a basic skeleton in which a spiro[cyclohexane-1,9'-fluorene] moiety with a cyano group (-CN) is linked to a condensed heteroaromatic ring moiety by a linking group (e.g., arylene).

[0047] Depending on the binding position with the linking group, the above-mentioned spiro[cyclohexane-1,9'-fluorene] moiety can be specified as a portion selected from the group consisting of the following portions CF1 to CF4.

[0048]

[0049] Depending on the different binding positions of the spiro[cyclohexane-1,9'-fluorene] moiety with the linking group and the different binding positions of the condensed heteroaromatic ring moiety with the linking group, the compound represented by the above chemical formula 1 can be a compound represented by any of the following chemical formulas 2 to 9. However, it is not limited to this.

[0050] [Chemical Formula 2]

[0051]

[0052] [Chemical Formula 3]

[0053]

[0054] [Chemical Formula 4]

[0055]

[0056] [Chemical Formula 5]

[0057]

[0058] [Chemical Formula 6]

[0059]

[0060] [Chemical Formula 7]

[0061]

[0062] [Chemical Formula 8]

[0063]

[0064] [Chemical Formula 9]

[0065]

[0066] Among the above chemical formulas 2 to 9,

[0067] X1 to X4, Y1, a, b, R1, R2, n, and L1 are each defined as described in Chemical Formula 1 above.

[0068] b1 can be an integer from 0 to 3, specifically 0 or 1.

[0069] In the chemical formula 1 of the present invention, the condensed heteroaromatic ring portion is a polycyclic form of nitrogen-containing heteroaromatic ring portion formed by the fusion of a monocyclic nitrogen-containing heteroaromatic ring (e.g., pyrimidine ring, triazine ring, pyridazine ring) and a benzo[a] ring (e.g., benzofuran ring, benzothiophene ring, indole ring, indene ring, etc.), which is an electron-withdrawing group (EWG) with excellent electron transport capability.

[0070] In such a condensed heteroaromatic ring moiety, X1 to X4 may be the same as or different from each other, and each can independently be N or C(Ar1), wherein at least two of X1 to X4 can be N, preferably two of X1 to X4 can be N. In this case, any carbon in C(Ar1) that is not N can also be connected to L1.

[0071] In addition, Y1 can be selected from a group consisting of O, S, Se, C(Ar2)(Ar3) and N(Ar4), specifically, it can be O or S.

[0072] As an example, depending on the differences between X1 to X4 mentioned above, the condensed heteroaromatic ring portion ( (Partially) can be selected from the group consisting of the following parts Mo1-1 to Mo1-34, specifically, the group consisting of the following parts Mo1-1 to Mo1-18 and Mo1-23 to Mo1-34. However, it is not limited to this.

[0073]

[0074]

[0075]

[0076] In the aforementioned parts Mo1-1 to Mo1-34,

[0077] Y1, b, R1, and R2 are each defined as described in Chemical Formula 1 above.

[0078] b1 can be an integer from 0 to 3, specifically, it can be 0 or 1.

[0079] In the chemical formula 1 of this invention, Ar1 to Ar4 may be the same as or different from each other, and each may be independently selected from hydrogen, deuterium (D), halogen (e.g., -F, -Cl, -Br, -I, etc.), cyano (-CN), nitro (-NO2), amino (-NH2), hydroxyl (-OH), C1~C 40 Alkyl groups, C2~C 40 alkenyl, C2~C 40 alkynyl group, C3~C 40 Cycloalkyl groups, heterocyclic alkyl groups with 3 to 40 nuclei, C6~C 60 aryl, heteroaryl with 5 to 60 nuclei, C1~C 40 alkoxy groups, C6~C 60 aryloxy groups, C1~C 40 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 aryl amino groups or condenses with adjacent groups (e.g., Ar1-R1, Ar2-Ar3, etc.) to form a condensation ring. Specifically, each group can be selected from hydrogen, C1~C1, C2~C3, etc. 40 Alkyl, C6~C 60 It is a group consisting of aryl groups and heteroaryl groups with 5 to 60 nuclei, or formed by condensation with adjacent groups (e.g., Ar1-R1, Ar2-Ar3, etc.). The condensation ring can be selected from C3 to C4. 60 Condensed aliphatic rings (specifically C3~C) 30 (condensed aliphatic ring), C6~C 60 Condensed aromatic rings (specifically C6~C6) 30 Condensed aromatic rings), condensed heteroaromatic rings priced between 5 and 60 yuan (specifically condensed heteroaromatic rings priced between 5 and 30 yuan), C3~C 60 One or more of the groups consisting of spiro rings and their combinations.

[0080] The alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, alkoxy, aryloxy, alkylsilyl, arylsilyl, alkylboryl, arylboryl, arylphosphinyl, arylphosphine oxide, arylamine, and condensation rings of Ar1 to Ar4 can each be independently selected from deuterium (D), halogens (e.g., -F, -Cl, -Br, -I, etc.), cyano (-CN), nitro (-NO2), amino (-NH2), hydroxyl (-OH), C1~C 40 Alkyl groups, C2~C 40 alkenyl, C2~C 40 alkynyl group, C3~C 40 Cycloalkyl groups, heterocyclic alkyl groups with 3 to 40 nuclei, C6~C 60 aryl groups, heteroaryl groups with 5 to 60 nuclei, C1~C 40 alkoxy groups, C6~C 60 aryloxy groups, C1~C 40 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 arylamines may be substituted or unsubstituted. Specifically, they may be selected from deuterium (D), halogens (e.g., -F, -Cl, -Br, -I, etc.), cyano (-CN), nitro (-NO2), amino (-NH2), hydroxyl (-OH), C1~C 40 Alkyl, C6~C 60 aryl groups, heteroaryl groups with 5 to 60 nuclei, and C6~C6 groups. 60 One or more substituents in the group consisting of arylamine groups may be substituted or unsubstituted, and more specifically, may be selected from deuterium (D), C1~C1, C2, C3, C4, C5, C6, C7, C8, C9 ... 20 Alkyl, C6~C 30 aryl groups, heteroaryl groups with 5 to 30 nuclei, and C6~C6 groups. 30 One or more substituents in the group consisting of arylamine groups are substituted or unsubstituted. In this case, when there are multiple substituents, they may be the same as or different from each other.

[0081] In the chemical formula 1 of this invention, a can be 1 or 2, specifically, it can be 1. In this case, a + b ≤ 5. Wherein, when a is 1 or 2, it means that hydrogen is replaced by a substituent (R1). In this case, when there are multiple R1s, the multiple R1s may be the same or different from each other.

[0082] R1 can be selected from hydrogen, deuterium (D), halogens (e.g., -F, -Cl, -Br, -I, etc.), cyano (-CN), nitro (-NO2), amino (-NH2), hydroxyl (-OH), C1~C 40 Alkyl groups, C2~C 40 alkenyl, C2~C 40 alkynyl group, C3~C 40 Cycloalkyl groups, heterocyclic alkyl groups with 3 to 40 nuclei, C6~C 60 aryl, heteroaryl with 5 to 60 nuclei, C1~C 40 alkoxy groups, C6~C 60 aryloxy groups, C1~C 40 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 arylamine groups, specifically, can be selected from C6~C6. 60 The group consisting of aryl groups and heteroaryl groups with 5 to 60 nuclei, more specifically, can be selected from C6 to C6. 30 It is a group composed of aryl groups and heteroaryl groups with 5 to 30 nuclei.

[0083] According to one example, R1 can be selected from the group consisting of phenyl, biphenyl, terphenyl and naphthyl, specifically, it can be phenyl or naphthyl.

[0084] The alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, alkoxy, aryloxy, alkylsilyl, arylsilyl, alkylboryl, arylboryl, arylphosphinyl, arylphosphine oxide, and arylamino groups of R1, as well as the arylene groups of L1, can each be independently selected from deuterium (D), halogens (e.g., -F, -Cl, -Br, -I, etc.), cyano (-CN), nitro (-NO2), amino (-NH2), hydroxyl (-OH), C1~C 40 Alkyl groups, C2~C 40 alkenyl, C2~C 40 alkynyl group, C3~C 40 Cycloalkyl groups, heterocyclic alkyl groups with 3 to 40 nuclei, C6~C 60 aryl groups, heteroaryl groups with 5 to 60 nuclei, C1~C 40 alkoxy groups, C6~C 60 aryloxy groups, C1~C 40 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 One or more substituents in the group consisting of arylamines may be substituted or unsubstituted. Specifically, they may be selected from deuterium (D), halogens (e.g., -F, -Cl, -Br, -I, etc.), cyano (-CN), nitro (-NO2), amino (-NH2), hydroxyl (-OH), C1~C 40 Alkyl, C6~C 60 aryl groups, heteroaryl groups with 5 to 60 nuclei, and C6~C6 groups. 60 One or more substituents in the group consisting of arylamine groups may be substituted or unsubstituted, and more specifically, may be selected from deuterium (D), C1~C1, C2, C3, C4, C5, C6, C7, C8, C9 ... 20 Alkyl, C6~C 30 aryl groups, heteroaryl groups with 5 to 30 nuclei, and C6~C6 groups. 30 One or more substituents in the group consisting of arylamine groups are substituted or unsubstituted. In this case, when there are multiple substituents, they may be the same as or different from each other.

[0085] In the chemical formula 1 of this invention, b can be an integer from 0 to 4, specifically, it can be 0 or 1.

[0086] When b is 0, it means that hydrogen is not substituted by a substituent (R2). On the other hand, when b is an integer from 1 to 4, it means that hydrogen is substituted by a substituent (R2). In this case, when there are multiple R2s, the multiple R1s may be the same or different from each other.

[0087] R2 can be selected from hydrogen, deuterium (D), halogens (e.g., -F, -Cl, -Br, -I, etc.), cyano (-CN), nitro (-NO2), amino (-NH2), hydroxyl (-OH), C1~C 40 Alkyl groups, C2~C 40 alkenyl, C2~C 40 alkynyl group, C3~C 40 Cycloalkyl groups, heterocyclic alkyl groups with 3 to 40 nuclei, C6~C 60 aryl, heteroaryl with 5 to 60 nuclei, C1~C 40 alkoxy groups, C6~C 60 aryloxy groups, C1~C 40 alkylsilyl, C6~C 60 arylsilyl, C1~C 40 alkylboron group, C6~C 60 arylboryl group, C6~C60 arylphosphine, C6~C 60 arylphosphine oxide and C6~C 60 The group composed of arylamine groups, specifically, can be selected from C6~C6. 60 The group consisting of aryl groups and heteroaryl groups with 5 to 60 nuclei, more specifically, can be selected from C6 to C6. 30 It is a group composed of aryl groups and heteroaryl groups with 5 to 30 nuclei.

[0088] The alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, alkoxy, aryloxy, alkylsilyl, arylsilyl, alkylboryl, arylboryl, arylphosphinyl, arylphosphine oxide, and arylamino groups of R2, as well as the arylene groups of L1, can each be independently selected from deuterium (D), halogens (e.g., -F, -Cl, -Br, -I, etc.), cyano (-CN), nitro (-NO2), amino (-NH2), hydroxyl (-OH), C1~C 40 Alkyl groups, C2~C 40 alkenyl, C2~C 40 alkynyl group, C3~C 40 Cycloalkyl groups, heterocyclic alkyl groups with 3 to 40 nuclei, C6~C 60 aryl groups, heteroaryl groups with 5 to 60 nuclei, C1~C 40 alkoxy groups, C6~C 60 aryloxy groups, C1~C 40 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 arylamines may be substituted or unsubstituted. Specifically, they may be selected from deuterium (D), halogens (e.g., -F, -Cl, -Br, -I, etc.), cyano (-CN), nitro (-NO2), amino (-NH2), hydroxyl (-OH), C1~C 40 Alkyl, C6~C 60 aryl groups, heteroaryl groups with 5 to 60 nuclei, and C6~C6 groups. 60 One or more substituents in the group consisting of arylamine groups may be substituted or unsubstituted, and more specifically, may be selected from deuterium (D), C1~C1, C2, C3, C4, C5, C6, C7, C8, C9 ... 20 Alkyl, C6~C 30 aryl groups, heteroaryl groups with 5 to 30 nuclei, and C6~C6 groups. 30One or more substituents in the group consisting of arylamine groups are substituted or unsubstituted. In this case, when there are multiple substituents, they may be the same as or different from each other.

[0089] In chemical formula 1 of this invention, n is an integer from 1 to 4. When n is an integer from 1 to 4, L1 acts as a divalent linker, having a C6~C6 configuration. 18 The subaryl group. Multiple L1 groups can be the same or different from each other.

[0090] According to one example, L1 can be a monocyclic arylene or a condensed or non-condensed arylene of 2 to 4 rings.

[0091] The arylene group of L1 mentioned above can be selected from deuterium (D), halogens (e.g., -F, -Cl, -Br, -I, etc.), cyano (-CN), nitro (-NO2), amino (-NH2), hydroxyl (-OH), C1~C 40 Alkyl groups, C2~C 40 alkenyl, C2~C 40 alkynyl group, C3~C 40 Cycloalkyl groups, heterocyclic alkyl groups with 3 to 40 nuclei, C6~C 60 aryl groups, heteroaryl groups with 5 to 60 nuclei, C1~C 40 alkoxy groups, C6~C 60 aryloxy groups, C1~C 40 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 arylamines may be substituted or unsubstituted. Specifically, they may be selected from deuterium (D), halogens (e.g., -F, -Cl, -Br, -I, etc.), cyano (-CN), nitro (-NO2), amino (-NH2), hydroxyl (-OH), C1~C 40 Alkyl, C6~C 60 aryl groups, heteroaryl groups with 5 to 60 nuclei, and C6~C6 groups. 60 One or more substituents in the group consisting of arylamine groups may be substituted or unsubstituted, and more specifically, may be selected from deuterium (D), C1~C1, C2, C3, C4, C5, C6, C7, C8, C9 ... 20 Alkyl, C6~C 30 aryl groups, heteroaryl groups with 5 to 30 nuclei, and C6~C6 groups. 30One or more substituents in the group consisting of arylamine groups are substituted or unsubstituted. In this case, when there are multiple substituents, they may be the same as or different from each other.

[0092] According to one example, L1 can be selected from the group consisting of the following linking groups L1-1 to L1-11, in which case multiple L1s can be the same or different from each other. However, it is not limited to this.

[0093]

[0094] Among the above-mentioned linking groups L1-1 to L1-11,

[0095] c is an integer from 0 to 4, specifically an integer from 0 to 2.

[0096] d is an integer from 0 to 6, specifically an integer from 0 to 2.

[0097] e is an integer from 0 to 8, specifically an integer from 0 to 2.

[0098] f is an integer from 0 to 7, specifically an integer from 0 to 2.

[0099] g is an integer from 0 to 3, specifically an integer from 0 to 2.

[0100] h is an integer from 0 to 5, specifically an integer from 0 to 2.

[0101] i is an integer from 0 to 10, specifically an integer from 0 to 2.

[0102] Multiple Rs may be the same or different from each other.

[0103] R can be selected from deuterium (D), halogens (e.g., -F, -Cl, -Br, -I, etc.), cyano (-CN), nitro (-NO2), amino (-NH2), hydroxyl (-OH), C1~C 40 Alkyl groups, C2~C 40 alkenyl, C2~C 40 alkynyl group, C3~C 40 Cycloalkyl groups, heterocyclic alkyl groups with 3 to 40 nuclei, C6~C 60 aryl groups, heteroaryl groups with 5 to 60 nuclei, C1~C 40 alkoxy groups, C6~C 60 aryloxy groups, C1~C 40 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~C60 The group composed of arylamine groups, specifically, can be selected from deuterium (D), cyano (-CN), C1~C1. 20 Alkyl, C6~C 30 aryl groups, heteroaryl groups with 5 to 30 nuclei, and C6~C6 groups. 30 It is a group composed of aryl amino groups.

[0104] Depending on the different L1 mentioned above, the compound represented by chemical formula 1 can be a compound represented by chemical formula 10 or 11. However, it is not limited to this.

[0105] [Chemical Formula 10]

[0106]

[0107] [Chemical Formula 11]

[0108]

[0109] In the above chemical formulas 10 and 11,

[0110] X1 to X4, Y, a, b, R1, and R2 are each defined in the above chemical formula 1.

[0111] b1 can be an integer from 0 to 3, specifically, it can be 0 or 1.

[0112] Depending on the difference between the condensed heteroaromatic ring portion and L1, the compound represented by the above chemical formula 1 can be a compound represented by any of the following chemical formulas 12 to 15. However, it is not limited to this.

[0113] [Chemical Formula 12]

[0114]

[0115] [Chemical Formula 13]

[0116]

[0117] [Chemical Formula 14]

[0118]

[0119] [Chemical Formula 15]

[0120]

[0121] In the above chemical formulas 12 to 15,

[0122] Y1, b, R2, and n are each defined in the same way as in the above chemical formula 1.

[0123] Multiple R1s may be the same or different from each other.

[0124] R1 can be chosen freely from C6 to C. 60 The group consists of aryl groups and heteroaryl groups with 5 to 60 nuclei.

[0125] The aryl and heteroaryl groups of R1 are each independently selected from deuterium (D), halogen, cyano, nitro, amino, hydroxyl, C1~C1. 40 Alkyl, C6~C 60 aryl groups, heteroaryl groups with 5 to 60 nuclei, and C6~C6 groups. 60 One or more substituents in the group consisting of arylamine groups are substituted or unsubstituted, and when there are multiple substituents, they may be the same as or different from each other.

[0126] b1 can be an integer from 0 to 3, specifically, it can be 0 or 1.

[0127] The compounds represented by chemical formula 1 of the present invention described above can be further specified as the following compounds, but are not limited thereto.

[0128]

[0129]

[0130]

[0131]

[0132]

[0133]

[0134]

[0135]

[0136]

[0137]

[0138]

[0139]

[0140] 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.

[0141] 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.

[0142] In this invention, "alkynyl" 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 triple bonds. Examples include ethynyl and 2-propynyl, but it is not limited to these.

[0143] 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.

[0144] 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 piperazineyl, but are not limited to these. Here, the number of nuclei refers to the number of atoms forming the ring, i.e., the ring atomic number.

[0145] 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. It may also include forms where two or more rings are simply attached to each other or condensed together. Examples of such aryl groups include phenyl, naphthyl, phenanthryl, anthracene, etc., but are not limited to these.

[0146] 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. Additionally, it may include forms where two or more rings are simply attached to or condensed together, and further, forms condensed with an aryl group. Examples of such heteroaryl groups include six-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, 2-isooxazolyl, 2-pyridinyl, and 2-pyrimidinyl, but are not limited thereto. Here, the number of atomic nuclei means the number of atoms that form a ring, i.e., the number of ring atoms.

[0147] In this invention, "alkoxy" is a monovalent substituent represented by R'O-, where R' means an alkyl group having 1 to 40 carbon atoms, and may include linear, branched, or cyclic structures. Examples of such alkoxy groups include methoxy, ethoxy, n-propoxy, 1-propoxy, tert-butoxy, n-butoxy, pentoxy, etc., but are not limited thereto.

[0148] In this invention, "aryloxy group" is a monovalent substituent represented by RO-, where R means 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.

[0149] In this invention, "alkylsilyl" means silyl substituted with alkyl groups having 1 to 40 carbon atoms, including not only monoalkylsilyl but also dialkylsilyl and trialkylsilyl.

[0150] In addition, "arylsilyl" means silyl groups that are replaced by aryl groups with 5 to 60 carbon atoms. It includes not only monoarylsilyl groups, but also polyarylsilyl groups such as diarylsilyl groups and triarylsilyl groups.

[0151] In this invention, "alkylboryl" means a boron group substituted with an alkyl group having 1 to 40 carbon atoms, and "arylboryl" means a boron group substituted with an aryl group having 6 to 60 carbon atoms.

[0152] 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.

[0153] In addition, in this invention, "arylphosphine" means a phosphine group that is replaced by an aryl group having 6 to 60 carbon atoms, including not only monoarylphosphine groups but also diarylphosphine groups.

[0154] In this invention, "arylphosphine oxide" means a phosphine oxide group that is replaced by an aryl group with 6 to 60 carbon atoms, including not only monoarylphosphine oxide groups but also diarylphosphine oxide groups.

[0155] In this invention, "arylamine" means an amine group that is replaced by an aryl group with 6 to 40 carbon atoms, including not only monoarylamines but also diarylamines.

[0156] 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 heteroaliphatic ring with 3 to 60 nuclei, a condensed heteroaromatic ring with 5 to 60 nuclei, or a C3~C4 ring. 60 The spiral ring or its combination. Here, the nucleus number means the number of atoms forming the ring, i.e., the ring atom number.

[0157] Organic electroluminescent elements

[0158] 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.

[0159] Specifically, such as 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.

[0160] The aforementioned organic layer 300 may comprise any one or more of a hole injection layer 310, a hole transport layer 320, a light-emitting layer 330, an electron transport layer 340, and an electron injection layer 350. Optionally, it may further comprise at least one of an electron transport auxiliary layer 360 and a hole transport auxiliary layer (not shown). In this case, at least one organic layer 300 comprises a compound represented by the aforementioned chemical formula 1. Specifically, the organic layer comprising the compound of the aforementioned chemical formula 1 may be an electron transport layer 340 or an electron transport auxiliary layer 360.

[0161] According to one example, the aforementioned organic layer or more may include a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer. Optionally, it may also include at least one of an electron transport auxiliary layer and a hole transport auxiliary layer. The aforementioned electron transport layer includes a compound represented by Chemical Formula 1. In this case, the compound represented by Chemical Formula 1 is included as an electron transport layer material in the organic electroluminescent element. In such an organic electroluminescent element, due to the compound of Chemical Formula 1, electrons can be easily injected from the cathode or the electron injection layer into the electron transport layer, and rapidly migrate from the electron transport layer to the light-emitting layer, thus resulting in strong 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. In addition, the compound of Chemical Formula 1 exhibits excellent thermal stability and electrochemical stability, thereby improving the performance of the organic electroluminescent element.

[0162] Such compounds of Formula 1 can be used alone or in combination with electron transport layer materials known in the art.

[0163] In this invention, the electron transport layer material that can be mixed with the compound of Formula 1 described above can be an electron transport substance or an n-type dopant commonly known in the art. Non-limiting examples of electron transport substances that can be used in this invention include oxazole compounds, isoxazole compounds, triazole compounds, isothiazole compounds, oxadiazole 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. Examples of n-type dopants that can be used in this invention include metals (e.g., alkali metals or alkaline earth metals) or complexes of the aforementioned metals; specifically, lithium quinolate (LiQ), etc.

[0164] In this invention, when the compound of chemical formula 1 and the electron transport layer material are mixed, their mixing ratio is not particularly limited and can be appropriately adjusted within the range known in the art.

[0165] According to another example, the aforementioned organic layer or more comprises a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport auxiliary layer, an electron transport layer, and an electron injection layer, wherein the electron transport auxiliary layer comprises a compound represented by Chemical Formula 1. In this case, the compound represented by Chemical Formula 1 is included as an electron transport auxiliary layer material in the organic electroluminescent element. The compound represented by Chemical Formula 1 has high triplet energy. Therefore, when the compound of Chemical Formula 1 is included as an electron transport auxiliary layer material, the efficiency of the organic electroluminescent element can be improved due to the triplet-triplet fusion (TTF) effect. Furthermore, the compound of Chemical Formula 1 can prevent excitons or holes generated in the light-emitting layer from diffusing to the electron transport layer adjacent to the light-emitting layer. Therefore, the number of excitons contributing to light emission in the light-emitting layer can be increased, thereby improving the luminous efficiency of the element, and the durability and stability of the element can be improved, effectively increasing the lifetime of the element.

[0166] Such compounds of Formula 1 can be used alone or in combination with electron transport auxiliary layer materials known in the art.

[0167] In this invention, the electron transport auxiliary layer material that can be used in combination with the compound of the above chemical formula 1 includes electron transport substances generally known in the art, such as oxadiazole derivatives, triazole derivatives, phenanthroline derivatives (e.g., BCP), nitrogen-containing heterocyclic derivatives, etc., but is not limited thereto.

[0168] 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 (see reference) can be sequentially stacked on a substrate. Figures 1 to 3 Furthermore, although not illustrated, it could be a structure in which an insulating or adhesive layer is inserted at the interface between the electrode and the organic layer.

[0169] According to one example, such as Figure 1 As shown, the organic electroluminescent device can have a structure formed by sequentially stacking 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 on a substrate. Optionally, as shown... Figure 2 As shown, an electron injection layer 350 can be provided between the electron transport layer 340 and the cathode 200. Additionally, an electron transport auxiliary layer 360 (see reference) can be provided between the light-emitting layer 330 and the electron transport layer 340. Figure 3 ).

[0170] In the organic electroluminescent element of the present invention, at least one of the organic layers 300 [e.g., electron transport layer 340] contains a compound represented by the above chemical formula 1. In addition, the organic layers and electrodes can be formed and manufactured by materials and methods known in the art.

[0171] The aforementioned organic layer can be formed by vacuum evaporation or solution coating. Examples of solution coating methods include spin coating, dip coating, doctor blade coating, inkjet printing, or thermal transfer, but are not limited to these.

[0172] 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.

[0173] 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.

[0174] 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.

[0175] Furthermore, there are no particular limitations on the hole injection layer, hole transport layer, light emission layer, electron injection layer, and hole transport auxiliary layer; any commonly known materials in the art may be used.

[0176] The present invention will be described in detail below through embodiments. However, the following embodiments are merely illustrative of the present invention, and the present invention is not limited to the following embodiments.

[0177] [Synthetic Example 1] Synthesis of Compound 1-1

[0178]

[0179] [Synthetic Example 1-1] Synthesis of Compound 1-1-ii

[0180] 100 g (418.3 mmol, 1 eq) of 2,4-dichlorobenzofurano[3,2-d]pyrimidine, 61.2 g (502.0 mmol, 1.2 eq) of phenylboronic acid, 419.3 g (16.7 mmol, 0.04 eq) of Pd(PPh3) and 115.6 g (836.6 mmol, 2 eq) of K2CO3 were added to 1500 ml of THF and 500 ml of H2O, and the mixture was heated under reflux and stirred for 6 hours. After the reaction was completed, the mixture was deactivated with sufficient water, then transferred to a separatory funnel, and the organic layer was separated and extracted by MC. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography to obtain the target compound 1-1-ii(2-chloro-4-phenylbenzofurano[3,2-d]pyrimidine) (103.3 g, yield 88%).

[0181] Mass spectrometry: [(M+H)] + ]:280.71

[0182] NMR ( 1 H): σ= 7.84(2H, d), 7.70-7.65(2H, m), 7.53-7.49(3H, m), 7.36(1H,t), 7.22(1H, t)

[0183] [Synthetic Examples 1-2] Synthesis of Compound 1-1-i

[0184] 103.3 g (368.1 mmol, 1 eq) of 2-chloro-4-phenylbenzofurano[3,2-d]pyrimidine, 63.3 g (404.9 mmol, 1.1 eq) of (2-chlorophenyl)boric acid, 12.8 g (11.0 mmol, 0.03 eq) of Pd(PPh3)4, and 101.8 g (736.2 mmol, 2 eq) of K2CO3 were added to 1500 ml of THF and 500 ml of H2O, and the mixture was heated under reflux and stirred for 4 hours. After the reaction was completed, the mixture was deactivated with sufficient water, then transferred to a separatory funnel, and the organic layer was separated and extracted by MC. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography to obtain the target compound 1-1-I (2-(2-chlorophenyl)-4-phenylbenzofurano[3,2-d]pyrimidine) (118.2 g, yield 90%).

[0185] Mass spectrometry: [(M+H)] + ]:356.81

[0186] NMR ( 1 H): σ= 7.84(2H, d) 7.70-7.53(8H, m), 7.387.36(3H, m), 7.22(1H, t)

[0187] [Synthetic Examples 1-3] Synthesis of Compound 1-1

[0188] 20 g (56.1 mmol, 1 eq) of 2-(2-chlorophenyl)-4-phenylbenzofurano[3,2-d]pyrimidine, 25.9 g (67.3 mmol, 1.2 eq) of 7'-(4,4,5,5-tetramethyl-1,3,2-dioxaboron-2-yl)spiro[cyclohexane-1,9'-fluorene]-2'-formonitrile, 0.4 g (1.7 mmol, 0.03 eq) of Pd(OAc), 2.7 g (5.6 mmol, 0.1 eq) of XPhos, and 18.6 g (134.5 mmol, 2 eq) of K2CO3 were added to 300 ml of toluene, 80 ml of EtOH, and 80 ml of H2O. The mixture was heated under reflux and stirred for 6 hours. After the reaction was complete, the mixture was deactivated using sufficient water, then transferred to a separatory funnel, and the organic layer was separated and extracted using MC. The extracted organic layer was concentrated, then adsorbed onto silica gel and purified by column chromatography to obtain the target compound 1-1(7'-(2-(4-phenylbenzofurano[3,2-d]pyrimidin-2-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-formonitrile) (26.0 g, yield 80%).

[0189] Mass spectrometry: [(M+H)] + ]:579.70

[0190] [Synthetic Examples 2 to 9]

[0191] The target compound C was synthesized using intermediates A and B as described in Table 1 below, except that the process was the same as in Synthesis Example 1.

[0192] [Table 1]

[0193]

[0194]

[0195] [Synthetic Example 10] Synthesis of Compounds 1-2

[0196]

[0197] [Synthetic Example 10-1] Synthesis of Compound 1-2-ii

[0198] 100 g (418.3 mmol, 1 eq) of 2,4-dichlorobenzofurano[3,2-d]pyrimidine, 61.2 g (502.0 mmol, 1.2 eq) of phenylboronic acid, 19.3 g (16.7 mmol, 0.04 eq) of Pd(PPh3)4, and 115.6 g (836.6 mmol, 2 eq) of K2CO3 were added to 1500 ml of THF and 500 ml of H2O, and the mixture was heated under reflux and stirred for 6 hours. After the reaction was completed, the mixture was deactivated with sufficient water, then transferred to a separatory funnel, and the organic layer was separated and extracted by MC. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography to obtain the target compound 1-2-ii(2-chloro-4-phenylbenzofurano[3,2-d]pyrimidine) (103.3 g, yield 88%).

[0199] Mass spectrometry: [(M+H)] + ]:280.71

[0200] NMR ( 1 H): σ= 7.84(2H, d), 7.70-7.65(2H, m), 7.53-7.49(3H, m), 7.36(1H,t), 7.22(1H, t)

[0201] [Synthetic Example 10-2] Synthesis of Compound 1-2-i

[0202] 103.3 g (368.1 mmol, 1 eq) of 2-chloro-4-phenylbenzofurano[3,2-d]pyrimidine, 63.3 g (404.9 mmol, 1.1 eq) of (2-chlorophenyl)boric acid, 12.8 g (11.0 mmol, 0.03 eq) of Pd(PPh3)4, and 101.8 g (736.2 mmol, 2 eq) of K2CO3 were added to 1500 ml of THF and 500 ml of H2O, and the mixture was heated under reflux and stirred for 4 hours. After the reaction was completed, the mixture was deactivated with sufficient water, then transferred to a separatory funnel, and the organic layer was separated and extracted by MC. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography to obtain the target compound 1-2-i(2-(2-chlorophenyl)-4-phenylbenzofurano[3,2-d]pyrimidine) (118.2 g, yield 90%).

[0203] Mass spectrometry: [(M+H)] + ]:356.81

[0204] NMR ( 1 H): σ= 7.84(2H, d) 7.70-7.53(8H,m), 7.387.36(3H, m), 7.22(1H,t)

[0205] [Synthetic Example 10-3] Synthesis of Compound 1-2

[0206] 20 g (56.1 mmol, 1 eq) of 2-(2-chlorophenyl)-4-phenylbenzofurano[3,2-d]pyrimidine, 25.9 g (67.3 mmol, 1.2 eq) of 6'-(4,4,5,5-tetramethyl-1,3,2-dioxaboron-2-yl)spiro[cyclohexane-1,9'-fluorene]-2'-formonitrile, 0.4 g (1.7 mmol, 0.03 eq) of Pd(OAc), 2.7 g (5.6 mmol, 0.1 eq) of XPhos, and 18.6 g (134.5 mmol, 2 eq) of K2CO3 were added to 300 ml of toluene, 80 ml of EtOH, and 80 ml of H2O. The mixture was heated under reflux and stirred for 6 hours. After the reaction was complete, the mixture was deactivated with sufficient water, then transferred to a separatory funnel, and the organic layer was separated and extracted using MC. The extracted organic layer was concentrated, then adsorbed onto silica gel and purified by column chromatography to obtain the target compound 1-2 {2'-(2-(4-phenylbenzofurano[3,2-d]pyrimidin-2-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-6'-formonitrile} (24.4 g, yield 75%).

[0207] Mass spectrometry: [(M+H)] + ]:579.70

[0208] [Synthetic Examples 11 to 17]

[0209] The target compound C was synthesized using intermediates A and B as described in Table 2 below, except that the process was the same as in Synthesis Example 10.

[0210] [Table 2]

[0211]

[0212]

[0213] [Synthetic Example 18] Synthesis of Compounds 1-3

[0214]

[0215] [Synthetic Example 18-1] Synthesis of Compound 1-3-ii

[0216] 100 g (418.3 mmol, 1 eq) of 2,4-dichlorobenzofurano[3,2-d]pyrimidine, 61.2 g (502.0 mmol, 1.2 eq) of phenylboronic acid, 19.3 g (16.7 mmol, 0.04 eq) of Pd(PPh3)4, and 115.6 g (836.6 mmol, 2 eq) of K2CO3 were added to 1500 ml of THF and 500 ml of H2O, and the mixture was heated under reflux and stirred for 6 hours. After the reaction was completed, the mixture was deactivated with sufficient water, then transferred to a separatory funnel, and the organic layer was separated and extracted by MC. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography to obtain the target compound 1-3-ii(2-chloro-4-phenylbenzofurano[3,2-d]pyrimidine) (103.3 g, yield 88%).

[0217] Mass spectrometry: [(M+H)] + ]:280.71

[0218] NMR ( 1 H): σ= 7.84(2H, d), 7.70-7.65(2H, m), 7.53-7.49(3H, m), 7.36(1H,t), 7.22(1H, t)

[0219] [Synthetic Example 18-2] Synthesis of Compound 1-3-i

[0220] 103.3 g (368.1 mmol, 1 eq) of 2-chloro-4-phenylbenzofurano[3,2-d]pyrimidine, 63.3 g (404.9 mmol, 1.1 eq) of (2-chlorophenyl)boric acid, 12.8 g (11.0 mmol, 0.03 eq) of Pd(PPh3)4, and 101.8 g (736.2 mmol, 2 eq) of K2CO3 were added to 1500 ml of THF and 500 ml of H2O, and the mixture was heated under reflux and stirred for 4 hours. After the reaction was completed, the mixture was deactivated with sufficient water, then transferred to a separatory funnel, and the organic layer was separated and extracted by MC. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography to obtain compound 1-3-i, namely 2-(2-chlorophenyl)-4-phenylbenzofurano[3,2-d]pyrimidine (118.2 g, yield 90%).

[0221] Mass spectrometry: [(M+H)] + ]:356.81

[0222] NMR ( 1 H): σ= 7.84(2H, d) 7.70-7.53(8H, m), 7.387.36(3H, m), 7.22(1H, t)

[0223] [Synthetic Example 18-3] Synthesis of Compounds 1-3

[0224] 20 g (56.1 mmol, 1 eq) of 2-(2-chlorophenyl)-4-phenylbenzofurano[3,2-d]pyrimidine, 25.9 g (67.3 mmol, 1.2 eq) of 2'-(4,4,5,5-tetramethyl-1,3,2-dioxaboron-2-yl)spiro[cyclohexane-1,9'-fluorene]-5'-formonitrile, 0.4 g (1.7 mmol, 0.03 eq) of Pd(OAc), 2.7 g (5.6 mmol, 0.1 eq) of XPhos, and 18.6 g (134.5 mmol, 2 eq) of K2CO3 were added to 300 ml of toluene, 80 ml of EtOH, and 80 ml of H2O. The mixture was heated under reflux and stirred for 6 hours. After the reaction was complete, the mixture was deactivated with sufficient water, then transferred to a separatory funnel, and the organic layer was separated and extracted using MC. The extracted organic layer was concentrated, then adsorbed onto silica gel and purified by column chromatography to obtain the target compound 1-3 {2'-(2-(4-phenylbenzofurano[3,2-d]pyrimidin-2-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-5'-formonitrile} (22.7 g, yield 70%).

[0225] Mass spectrometry: [(M+H)] + ]:579.70

[0226] [Synthetic Examples 19 and 20]

[0227] The target compound C was synthesized using intermediates A and B as described in Table 2 below, except that the process was the same as in Synthesis Example 18.

[0228] [Table 3]

[0229]

[0230] [Synthetic Example 21] Synthesis of Compounds 1-4

[0231]

[0232] [Synthetic Example 21-1] Synthesis of Compound 1-4-ii

[0233] 100 g (418.3 mmol, 1 eq) of 2,4-dichlorobenzofurano[3,2-d]pyrimidine, 61.2 g (502.0 mmol, 1.2 eq) of phenylboronic acid, 19.3 g (16.7 mmol, 0.04 eq) of Pd(PPh3)4, and 115.6 g (836.6 mmol, 2 eq) of K2CO3 were added to 1500 ml of THF and 500 ml of H2O, and the mixture was heated under reflux and stirred for 6 hours. After the reaction was completed, the mixture was deactivated with sufficient water, then transferred to a separatory funnel, and the organic layer was separated and extracted by MC. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography to obtain the target compound 1-4-ii(2-chloro-4-phenylbenzofurano[3,2-d]pyrimidine) (103.3 g, yield 88%).

[0234] Mass spectrometry: [(M+H)] + ]:280.71

[0235] NMR ( 1 H): σ= 7.84(2H, d), 7.70-7.65(2H, m), 7.53-7.49(3H, m), 7.36(1H,t), 7.22(1H, t)

[0236] [Synthetic Example 21-2] Synthesis of Compound 1-4-i

[0237] 103.3 g (368.1 mmol, 1 eq) of 2-chloro-4-phenylbenzofurano[3,2-d]pyrimidine, 63.3 g (404.9 mmol, 1.1 eq) of (2-chlorophenyl)boric acid, 12.8 g (11.0 mmol, 0.03 eq) of Pd(PPh3)4, and 101.8 g (736.2 mmol, 2 eq) of K2CO3 were added to 1500 ml of THF and 500 ml of H2O, and the mixture was heated under reflux and stirred for 4 hours. After the reaction was completed, the mixture was deactivated with sufficient water, then transferred to a separatory funnel, and the organic layer was separated and extracted by MC. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography to obtain the target compound 1-4-i(2-(2-chlorophenyl)-4-phenylbenzofurano[3,2-d]pyrimidine) (118.2 g, yield 90%).

[0238] Mass spectrometry: [(M+H)] + ]:356.81

[0239] NMR ( 1 H): σ= 7.84(2H, d) 7.70-7.53(8H,m), 7.387.36(3H, m), 7.22(1H,t)

[0240] [Synthetic Examples 21-3] Synthesis of Compounds 1-4

[0241] 20 g (56.1 mmol, 1 eq) of 2-(2-chlorophenyl)-4-phenylbenzofurano[3,2-d]pyrimidine, 25.9 g (67.3 mmol, 1.2 eq) of 6'-(4,4,5,5-tetramethyl-1,3,2-dioxaboron-2-yl)spiro[cyclohexane-1,9'-fluorene]-2'-formonitrile, 0.4 g (1.7 mmol, 0.03 eq) of Pd(OAc), 2.7 g (5.6 mmol, 0.1 eq) of XPhos, and 18.6 g (134.5 mmol, 2 eq) of K2CO3 were added to 300 ml of toluene, 80 ml of EtOH, and 80 ml of H2O. The mixture was heated under reflux and stirred for 6 hours. After the reaction was complete, the mixture was deactivated with sufficient water, then transferred to a separatory funnel, and the organic layer was separated and extracted using MC. The extracted organic layer was concentrated, then adsorbed onto silica gel and purified by column chromatography to obtain the target compound 1-4{6'-(2-(4-phenylbenzofurano[3,2-d]pyrimidin-2-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-formonitrile} (25.3 g, yield 78%).

[0242] Mass spectrometry: [(M+H)] + ]:579.70

[0243] [Synthetic Examples 22 to 24]

[0244] The target compound C was synthesized using intermediates A and B as described in Table 4 below, except that the process was the same as in Synthesis Example 21.

[0245] [Table 4]

[0246]

[0247] [Synthetic Example 25] Synthesis of Compounds 1-7

[0248]

[0249] [Synthetic Example 25-1] Synthesis of Compound 1-7-ii

[0250] 100 g (418.3 mmol, 1 eq) of 2,4-dichlorobenzofurano[3,2-d]pyrimidine, 61.2 g (502.0 mmol, 1.2 eq) of phenylboronic acid, 19.3 g (16.7 mmol, 0.04 eq) of Pd(PPh3)4, and 115.6 g (836.6 mmol, 2 eq) of K2CO3 were added to 1500 ml of THF and 500 ml of H2O, and the mixture was heated under reflux and stirred for 6 hours. After the reaction was completed, the mixture was deactivated with sufficient water, then transferred to a separatory funnel, and the organic layer was separated and extracted by MC. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography to obtain the target compound 1-7-ii(2-chloro-4-phenylbenzofurano[3,2-d]pyrimidine) (104.5 g, yield 89%).

[0251] Mass spectrometry: [(M+H)] + ]:280.71

[0252] NMR ( 1 H): σ= 7.84(2H, d), 7.70-7.65(2H, m), 7.53-7.49(3H, m), 7.36(1H,t), 7.22(1H, t)

[0253] [Synthetic Example 25-2] Synthesis of Compound 1-7-i

[0254] 104.5 g (372.3 mmol, 1 eq) of 2-chloro-4-phenylbenzofurano[3,2-d]pyrimidine, 64.0 g (409.5 mmol, 1.1 eq) of (2-chlorophenyl)boric acid, 12.9 g (11.2 mmol, 0.03 eq) of Pd(PPh3)4, and 102.9 g (744.6 mmol, 2 eq) of K2CO3 were added to 1550 ml of THF and 520 ml of H2O, and the mixture was heated under reflux and stirred for 4 hours. After the reaction was completed, the mixture was deactivated with sufficient water, then transferred to a separatory funnel, and the organic layer was separated and extracted by MC. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography to obtain the target compound 1-7-I{2-(2-chlorophenyl)-4-phenylbenzofurano[3,2-d]pyrimidine} (122.2 g, yield 92%).

[0255] Mass spectrometry: [(M+H)] + ] : 356.81

[0256] NMR ( 1 H): σ= 7.84(2H, d) 7.70-7.53(8H,m), 7.387.36(3H, m), 7.22(1H, t)

[0257] [Synthetic Example 25-3] Synthesis of Compounds 1-7

[0258] 20 g (56.1 mmol, 1 eq) of 2-(2-chlorophenyl)-4-phenylbenzofurano[3,2-d]pyrimidine, 25.9 g (67.3 mmol, 1.2 eq) of 5'-(4,4,5,5-tetramethyl-1,3,2-dioxaboron-2-yl)spiro[cyclohexane-1,9'-fluorene]-2'-formonitrile, 0.4 g (1.7 mmol, 0.03 eq) of Pd(OAc), 2.7 g (5.6 mmol, 0.1 eq) of XPhos, and 18.6 g (134.5 mmol, 2 eq) of K2CO3 were added to 300 ml of toluene, 80 ml of EtOH, and 80 ml of H2O. The mixture was heated under reflux and stirred for 6 hours. After the reaction was complete, the mixture was deactivated using sufficient water, then transferred to a separatory funnel, and the organic layer was separated and extracted using MC. The extracted organic layer was concentrated, then adsorbed onto silica gel and purified by column chromatography to obtain compound 1-7, namely 5'-(2-(4-phenylbenzofurano[3,2-d]pyrimidin-2-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carboxynitrile (24.0 g, yield 74%).

[0259] Mass spectrometry: [(M+H)] + ]:579.70

[0260] [Synthetic Examples 26 to 28]

[0261] The target compound C was synthesized using intermediates A and B as described in Table 5 below, except that the process was the same as in Synthesis Example 25.

[0262] [Table 5]

[0263]

[0264] [Synthetic Example 29] Synthesis of Compounds 1-8

[0265]

[0266] [Synthetic Example 29-1] Synthesis of Compound 1-8-ii

[0267] 100 g (418.3 mmol, 1 eq) of 2,4-dichlorobenzofurano[3,2-d]pyrimidine, 61.2 g (502.0 mmol, 1.2 eq) of phenylboronic acid, 19.3 g (16.7 mmol, 0.04 eq) of Pd(PPh3)4, and 115.6 g (836.6 mmol, 2 eq) of K2CO3 were added to 1500 ml of THF and 500 ml of H2O, and the mixture was heated under reflux and stirred for 6 hours. After the reaction was completed, the mixture was deactivated with sufficient water, then transferred to a separatory funnel, and the organic layer was separated and extracted by MC. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography to obtain the target compound 1-8-ii(2-chloro-4-phenylbenzofurano[3,2-d]pyrimidine) (104.5 g, yield 89%).

[0268] Mass spectrometry: [(M+H)] + ]:280.71

[0269] NMR ( 1 H): σ= 7.84(2H, d), 7.70-7.65(2H, m), 7.53-7.49(3H, m), 7.36(1H,t), 7.22(1H, t)

[0270] [Synthetic Example 29-2] Synthesis of Compound 1-8-i

[0271] 104.5 g (372.3 mmol, 1 eq) of 2-chloro-4-phenylbenzofurano[3,2-d]pyrimidine, 64.0 g (409.5 mmol, 1.1 eq) of (2-chlorophenyl)boric acid, 12.9 g (11.2 mmol, 0.03 eq) of Pd(PPh3)4, and 102.9 g (744.6 mmol, 2 eq) of K2CO3 were added to 1550 ml of THF and 520 ml of H2O, and the mixture was heated under reflux and stirred for 4 hours. After the reaction was completed, the mixture was deactivated with sufficient water, then transferred to a separatory funnel, and the organic layer was separated and extracted by MC. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography to obtain the target compound 1-8-I{2-(2-chlorophenyl)-4-phenylbenzofurano[3,2-d]pyrimidine} (122.2 g, yield 92%).

[0272] Mass spectrometry: [(M+H)] + ]:356.81

[0273] NMR ( 1 H): σ= 7.84(2H, d) 7.70-7.53(8H, m), 7.387.36(3H, m), 7.22(1H, t)

[0274] [Synthetic Example 29-3] Synthesis of Compounds 1-8

[0275] 20 g (56.1 mmol, 1 eq) of 2-(2-chlorophenyl)-4-phenylbenzofurano[3,2-d]pyrimidine, 25.9 g (67.3 mmol, 1.2 eq) of 5'-(4,4,5,5-tetramethyl-1,3,2-dioxaboron-2-yl)spiro[cyclohexane-1,9'-fluorene]-3'-formonitrile, 0.4 g (1.7 mmol, 0.03 eq) of Pd(OAc), 2.7 g (5.6 mmol, 0.1 eq) of XPhos, and 18.6 g (134.5 mmol, 2 eq) of K2CO3 were added to 300 ml of toluene, 80 ml of EtOH, and 80 ml of H2O. The mixture was heated under reflux and stirred for 6 hours. After the reaction was complete, the mixture was deactivated using sufficient water, then transferred to a separatory funnel, and the organic layer was separated and extracted using MC. The extracted organic layer was concentrated, then adsorbed onto silica gel and purified by column chromatography to obtain the target compound 1-8{5'-(2-(4-phenylbenzofurano[3,2-d]pyrimidin-2-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-3'-formonitrile} (22.3 g, yield 69%).

[0276] Mass spectrometry: [(M+H)] + ]:579.70

[0277] [Synthetic Examples 30 and 31]

[0278] The target compound C was synthesized using intermediates A and B as described in Table 6 below, except that the process was the same as in Synthesis Example 29.

[0279] [Table 6]

[0280]

[0281] [Synthetic Example 32] Synthesis of Compounds 1-61

[0282]

[0283] [Synthetic Example 32-1] Synthesis of Compound 1-61-ii

[0284] 100 g (418.3 mmol, 1 eq) of 2,4-dichlorobenzofurano[3,2-d]pyrimidine, 61.2 g (502.0 mmol, 1.2 eq) of phenylboronic acid, 19.3 g (16.7 mmol, 0.04 eq) of Pd(PPh3)4, and 115.6 g (836.6 mmol, 2 eq) of K2CO3 were added to 1500 ml of THF and 500 ml of H2O, and the mixture was heated under reflux and stirred for 6 hours. After the reaction was completed, the mixture was deactivated with sufficient water, then transferred to a separatory funnel, and the organic layer was separated and extracted by MC. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography to obtain the target compound 1-61-ii (2-chloro-4-phenylbenzofurano[3,2-d]pyrimidine) (104.5 g, yield 89%).

[0285] Mass spectrometry: [(M+H)] + ]:280.71

[0286] NMR ( 1 H): σ= 7.84(2H, d), 7.70-7.65(2H, m), 7.53-7.49(3H, m), 7.36(1H,t), 7.22(1H, t)

[0287] [Synthetic Example 32-2] Synthesis of Compound 1-61-i

[0288] 104.5 g (372.3 mmol, 1 eq) of 2-chloro-4-phenylbenzofurano[3,2-d]pyrimidine, 64.0 g (409.5 mmol, 1.1 eq) of (2-chlorophenyl)boric acid, 12.9 g (11.2 mmol, 0.03 eq) of Pd(PPh3)4, and 102.9 g (744.6 mmol, 2 eq) of K2CO3 were added to 1550 ml of THF and 520 ml of H2O, and the mixture was heated under reflux and stirred for 4 hours. After the reaction was completed, the mixture was deactivated with sufficient water, then transferred to a separatory funnel, and the organic layer was separated and extracted by MC. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography to obtain the target compound 1-61-i{2-(2-chlorophenyl)-4-phenylbenzofurano[3,2-d]pyrimidine} (122.2 g, yield 92%).

[0289] Mass spectrometry: [(M+H)] + ] : 356.81

[0290] NMR ( 1 H): σ= 7.84(2H, d) 7.70-7.53(8H, m), 7.387.36(3H, m), 7.22(1H, t)

[0291] [Synthetic Examples 32-3] Synthesis of Compounds 1-61

[0292] 20 g (56.1 mmol, 1 eq) of 2-(2-chlorophenyl)-4-phenylbenzofurano[3,2-d]pyrimidine, 31.0 g (67.3 mmol, 1.2 eq) of 4-(2'-(4,4,5,5-tetramethyl-1,3,2-dioxaborane-2-yl)spiro[cyclohexane-1,9'-fluorene]-7'-yl)benzyl nitrile, 0.4 g (1.7 mmol, 0.03 eq) of Pd(OAc), 2.7 g (5.6 mmol, 0.1 eq) of XPhos, and 18.6 g (134.5 mmol, 2 eq) of K2CO3 were added to 300 ml of toluene, 80 ml of EtOH, and 80 ml of H2O. The mixture was heated under reflux and stirred for 6 hours. After the reaction was complete, the mixture was deactivated with sufficient water, then transferred to a separatory funnel, and the organic layer was separated and extracted using MC. The extracted organic layer was concentrated, then adsorbed onto silica gel and purified by column chromatography to obtain the target compound 1-61, namely 4-(2'-(2-(4-phenylbenzofurano[3,2-d]pyrimidin-2-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-7'-yl)benzylnitrile (22.3 g, yield 69%).

[0293] Mass spectrometry: [(M+H)] + ]:655.80

[0294] [Synthetic Examples 33 to 35]

[0295] The target compound d was synthesized using intermediates A, B and c as described in Table 7 below, except that the process was the same as in Synthesis Example 32.

[0296] [Table 7]

[0297]

[0298] [Synthetic Example 36] Synthesis of Compounds 1-76

[0299]

[0300] [Synthetic Example 36-1] Synthesis of Compound 1-76-ii

[0301] 60 g (251.0 mmol, 1 eq) of 2,4-dichlorobenzofurano[3,2-d]pyrimidine, 39.2 g (251.0 mmol, 1.0 eq) of (2-chlorophenyl)boric acid, 11.6 g (10.0 mmol, 0.04 eq) of Pd(PPh3)4, and 69.4 g (502.0 mmol, 2 eq) of K2CO3 were added to 900 ml of THF and 300 ml of H2O, and the mixture was heated under reflux and stirred for 4 hours. After the reaction was completed, the mixture was deactivated with sufficient water, then transferred to a separatory funnel, and the organic layer was separated and extracted by MC. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography to obtain the target compound 1-76-ii{2-chloro-4-(2-chlorophenyl)benzofurano[3,2-d]pyrimidine} (67.2 g, yield 85%).

[0302] Mass spectrometry: [(M+H)] + ]:315.15

[0303] NMR ( 1 H): σ= 7.71-7.65(4H, m), 7.38-7.36(3H, m), 7.22(1H, t)

[0304] [Synthetic Example 36-2] Synthesis of Compound 1-76-i

[0305] 67.2 g (213.3 mmol, 1 eq) of 2-chloro-4-(2-chlorophenyl)benzofurano[3,2-d]pyrimidine, 31.2 g (256.0 mmol, 1.2 eq) of phenylboronic acid, 7.4 g (6.4 mmol, 0.03 eq) of Pd(PPh3)4, and 59.0 g (426.7 mmol, 2 eq) of K2CO3 were added to 1000 ml of THF and 400 ml of H2O, and the mixture was heated under reflux with stirring for 4 hours. After the reaction was completed, the mixture was deactivated with sufficient water, then transferred to a separatory funnel, and the organic layer was separated and extracted by MC. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography to obtain the target compound 1-76-i{4-(2-chlorophenyl)-2-phenylbenzofurano[3,2-d]pyrimidine} (122.2 g, yield 92%).

[0306] Mass spectrometry: [(M+H)] + ]:356.81

[0307] NMR ( 1 H): σ= 8.35(2H, d), 7.71-7.65(4H, m), 7.50(3H, d), 7.37-7.36(3H,m), 7.22(1H, t)

[0308] [Synthetic Example 36-3] Synthesis of Compounds 1-76

[0309] 20 g (56.1 mmol, 1 eq) of 4-(2-chlorophenyl)-2-phenylbenzofurano[3,2-d]pyrimidine, 25.9 g (67.3 mmol, 1.2 eq) of 7'-(4,4,5,5-tetramethyl-1,3,2-dioxaboron-2-yl)spiro[cyclohexane-1,9'-fluorene]-2'-formonitrile, 0.4 g (1.7 mmol, 0.03 eq) of Pd(OAc), 2.7 g (5.6 mmol, 0.1 eq) of XPhos, and 18.6 g (134.5 mmol, 2 eq) of K2CO3 were added to 300 ml of toluene, 80 ml of EtOH, and 80 ml of H2O. The mixture was heated under reflux and stirred for 8 hours. After the reaction was complete, the mixture was deactivated using sufficient water, then transferred to a separatory funnel, and the organic layer was separated and extracted using MC. The extracted organic layer was concentrated, then adsorbed onto silica gel and purified by column chromatography to obtain the target compound 1-76{7'-(2-(2-phenylbenzofurano[3,2-d]pyrimidin-4-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carboxynitrile} (24.0 g, yield 74%).

[0310] Mass spectrometry: [(M+H)] + ]:579.70

[0311] [Synthetic Examples 37 to 40]

[0312] The target compound D was synthesized using intermediates A, B and C as described in Table 8 below, except that the process was the same as in Synthesis Example 36.

[0313] [Table 8]

[0314]

[0315] [Synthetic Example 41] Synthesis of Compound 2-1

[0316]

[0317] [Synthetic Example 41-1] Synthesis of Compound 2-1-ii

[0318] 100 g (392.0 mmol, 1 eq) of 2,4-dichlorobenzo[4,5]thieno[3,2-d]pyrimidine, 52.6 g (431.2 mmol, 1.1 eq) of phenylboronic acid, 18.1 g (15.7 mmol, 0.04 eq) of Pd(PPh3)4, and 108.3 g (783.9 mmol, 2 eq) of K2CO3 were added to 1500 ml of THF and 500 ml of H2O, and the mixture was heated under reflux and stirred for 6 hours. After the reaction was completed, the mixture was deactivated with sufficient water, then transferred to a separatory funnel, and the organic layer was separated and extracted by MC. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography to obtain the target compound 2-1-ii{2-chloro-4-phenylbenzo[4,5]thieno[3,2-d]pyrimidine} (100.0 g, yield 86%).

[0319] Mass spectrometry: [(M+H)] + ]:296.77

[0320] NMR ( 1 H): σ= 8.05(1H, d), 7.93(1H, d), 7.84(2H, d), 7.53-7.42(5H,m)

[0321] [Synthetic Example 41-2] Synthesis of Compound 2-1-i

[0322] 100.0 g (337.1 mmol, 1 eq) of 2-chloro-4-phenylbenzo[4,5]thieno[3,2-d]pyrimidine, 58.0 g (370.8 mmol, 1.1 eq) of (2-chlorophenyl)boric acid, 11.7 g (10.1 mmol, 0.03 eq) of Pd(PPh3)4, and 93.2 g (674.2 mmol, 2 eq) of K2CO3 were added to 1500 ml of THF and 600 ml of H2O, and the mixture was heated under reflux with stirring for 4 hours. After the reaction was completed, the mixture was deactivated with sufficient water, then transferred to a separatory funnel, and the organic layer was separated and extracted by MC. The extracted organic layer was concentrated, then adsorbed onto silica gel and purified by column chromatography to obtain the target compound 2-1-i{2-(2-chlorophenyl)-4-phenylbenzo[4,5]thiopheno[3,2-d]pyrimidine} (115.6 g, yield 89%).

[0323] Mass spectrometry: [(M+H)] + ]:372.87

[0324] NMR ( 1H): σ= 8.05(1H, d), 7.93(1H, d), 7.84(2H, d), 7.71(1H, d), 7.61-7.38(8H, m)

[0325] [Synthetic Example 41-3] Synthesis of Compound 2-1

[0326] 20 g (53.6 mmol, 1 eq) of 2-(2-chlorophenyl)-4-phenylbenzo[4,5]thieno[3,2-d]pyrimidine, 24.8 g (64.4 mmol, 1.2 eq) of 7'-(4,4,5,5-tetramethyl-1,3,2-dioxaboron-2-yl)spiro[cyclohexane-1,9'-fluorene]-2'-formonitrile, 0.4 g (1.6 mmol, 0.03 eq) of Pd(OAc), 2.6 g (5.4 mmol, 0.1 eq) of XPhos, and 17.8 g (128.7 mmol, 2 eq) of K2CO3 were added to 300 ml of toluene, 80 ml of EtOH, and 80 ml of H2O. The mixture was heated under reflux and stirred for 6 hours. After the reaction was complete, the mixture was deactivated with sufficient water, then transferred to a separatory funnel, and the organic layer was separated and extracted using MC. The extracted organic layer was concentrated, then adsorbed onto silica gel and purified by column chromatography to obtain the target compound 2-1{7'-(2-(4-phenylbenzo[4,5]thieno[3,2-d]pyrimidin-2-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carboxynitrile} (23.6 g, yield 74%).

[0327] Mass spectrometry: [(M+H)] + ]:595.76

[0328] [Synthetic Examples 42 to 47]

[0329] The target compound C was synthesized using intermediates A and B as described in Table 9 below, except that the process was the same as in Synthesis Example 41.

[0330] [Table 9]

[0331]

[0332]

[0333] [Synthetic Example 48] Synthesis of Compound 2-2

[0334]

[0335] [Synthetic Example 48-1] Synthesis of Compound 2-2-ii

[0336] 100 g (392.0 mmol, 1 eq) of 2,4-dichlorobenzo[4,5]thieno[3,2-d]pyrimidine, 52.6 g (431.2 mmol, 1.1 eq) of phenylboronic acid, 18.1 g (15.7 mmol, 0.04 eq) of Pd(PPh3)4, and 108.3 g (783.9 mmol, 2 eq) of K2CO3 were added to 1500 ml of THF and 500 ml of H2O, and the mixture was heated under reflux and stirred for 6 hours. After the reaction was completed, the mixture was deactivated with sufficient water, then transferred to a separatory funnel, and the organic layer was separated and extracted by MC. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography to obtain the target compound 2-2-ii{2-chloro-4-phenylbenzo[4,5]thieno[3,2-d]pyrimidine} (100.0 g, yield 86%).

[0337] Mass spectrometry: [(M+H)] + ]:296.77

[0338] NMR ( 1 H): σ= 8.05(1H, d), 7.93(1H, d), 7.84(2H, d), 7.53-7.42(5H,m)

[0339] [Synthetic Example 48-2] Synthesis of Compound 2-2-i

[0340] 100.0 g (337.1 mmol, 1 eq) of 2-chloro-4-phenylbenzo[4,5]thieno[3,2-d]pyrimidine, 58.0 g (370.8 mmol, 1.1 eq) of (2-chlorophenyl)boric acid, 11.7 g (10.1 mmol, 0.03 eq) of Pd(PPh3)4, and 93.2 g (674.2 mmol, 2 eq) of K2CO3 were added to 1500 ml of THF and 600 ml of H2O, and the mixture was heated under reflux with stirring for 4 hours. After the reaction was completed, the mixture was deactivated with sufficient water, then transferred to a separatory funnel, and the organic layer was separated and extracted by MC. The extracted organic layer was concentrated, then adsorbed onto silica gel and purified by column chromatography to obtain the target compound 2-2-i{2-(2-chlorophenyl)-4-phenylbenzo[4,5]thiopheno[3,2-d]pyrimidine} (115.6 g, yield 89%).

[0341] Mass spectrometry: [(M+H)] + ]:372.87

[0342] NMR ( 1H): σ= 8.05(1H, d), 7.93(1H,d), 7.84(2H, d), 7.71(1H, d), 7.61-7.38(8H, m)

[0343] [Synthetic Example 48-3] Synthesis of Compound 2-2

[0344] 20 g (53.6 mmol, 1 eq) of 2-(2-chlorophenyl)-4-phenylbenzo[4,5]thieno[3,2-d]pyrimidine, 24.8 g (64.4 mmol, 1.2 eq) of 2'-(4,4,5,5-tetramethyl-1,3,2-dioxaborane-2-yl)spiro[cyclohexane-1,9'-fluorene]-6'-formonitrile, 0.4 g (1.6 mmol, 0.03 eq) of Pd(OAc), 2.6 g (5.4 mmol, 0.1 eq) of XPhos, and 17.8 g (128.7 mmol, 2 eq) of K2CO3 were added to 300 ml of toluene, 80 ml of EtOH, and 80 ml of H2O. The mixture was heated under reflux and stirred for 6 hours. After the reaction was complete, the mixture was deactivated using sufficient water, then transferred to a separatory funnel, and the organic layer was separated and extracted using MC. The extracted organic layer was concentrated, then adsorbed onto silica gel and purified by column chromatography to obtain the target compound 2-2{2'-(2-(4-phenylbenzo[4,5]thieno[3,2-d]pyrimidin-2-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-6'-formonitrile} (23.0 g, yield 72%).

[0345] Mass spectrometry: [(M+H)] + ]:595.76

[0346] [Synthetic Examples 49 to 51]

[0347] The target compound C was synthesized using intermediates A and B as described in Table 10 below, except that the process was the same as in Synthesis Example 48.

[0348] [Table 10]

[0349]

[0350] [Synthetic Example 52] Synthesis of Compounds 2-4

[0351]

[0352] [Synthetic Example 52-1] Synthesis of Compound 2-4-ii

[0353] 100 g (392.0 mmol, 1 eq) of 2,4-dichlorobenzo[4,5]thieno[3,2-d]pyrimidine, 52.6 g (431.2 mmol, 1.1 eq) of phenylboronic acid, 18.1 g (15.7 mmol, 0.04 eq) of Pd(PPh3)4, and 108.3 g (783.9 mmol, 2 eq) of K2CO3 were added to 1500 ml of THF and 500 ml of H2O, and the mixture was heated under reflux and stirred for 6 hours. After the reaction was completed, the mixture was deactivated with sufficient water, then transferred to a separatory funnel, and the organic layer was separated and extracted by MC. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography to obtain the target compound 2-4-ii{2-chloro-4-phenylbenzo[4,5]thieno[3,2-d]pyrimidine} (100.0 g, yield 86%).

[0354] Mass spectrometry: [(M+H)] + ]:296.77

[0355] NMR ( 1 H): σ= 8.05(1H, d), 7.93(1H, d), 7.84(2H, d), 7.53-7.42(5H,m)

[0356] [Synthetic Example 52-2] Synthesis of Compound 2-4-i

[0357] 100.0 g (337.1 mmol, 1 eq) of 2-chloro-4-phenylbenzo[4,5]thieno[3,2-d]pyrimidine, 58.0 g (370.8 mmol, 1.1 eq) of (2-chlorophenyl)boric acid, 11.7 g (10.1 mmol, 0.03 eq) of Pd(PPh3)4, and 93.2 g (674.2 mmol, 2 eq) of K2CO3 were added to 1500 ml of THF and 600 ml of H2O, and the mixture was heated under reflux with stirring for 4 hours. After the reaction was completed, the mixture was deactivated with sufficient water, then transferred to a separatory funnel, and the organic layer was separated and extracted by MC. The extracted organic layer was concentrated, then adsorbed onto silica gel and purified by column chromatography to obtain the target compound 2-4-I{2-(2-chlorophenyl)-4-phenylbenzo[4,5]thiopheno[3,2-d]pyrimidine} (115.6 g, yield 89%).

[0358] Mass spectrometry: [(M+H)] + ]:372.87

[0359] NMR ( 1H): σ= 8.05(1H, d), 7.93(1H, d), 7.84(2H, d), 7.71(1H, d), 7.61-7.38(8H, m)

[0360] [Synthetic Example 52-3] Synthesis of Compound 2-4

[0361] 20 g (53.6 mmol, 1 eq) of 2-(2-chlorophenyl)-4-phenylbenzo[4,5]thieno[3,2-d]pyrimidine, 24.8 g (64.4 mmol, 1.2 eq) of 6'-(4,4,5,5-tetramethyl-1,3,2-dioxaborane-2-yl)spiro[cyclohexane-1,9'-fluorene]-2'-formonitrile, 0.4 g (1.6 mmol, 0.03 eq) of Pd(OAc), 2.6 g (5.4 mmol, 0.1 eq) of XPhos, and 17.8 g (128.7 mmol, 2 eq) of K2CO3 were added to 300 ml of toluene, 80 ml of EtOH, and 80 ml of H2O. The mixture was heated under reflux and stirred for 6 hours. After the reaction was complete, the mixture was deactivated using sufficient water, then transferred to a separatory funnel, and the organic layer was separated and extracted using MC. The extracted organic layer was concentrated, then adsorbed onto silica gel and purified by column chromatography to obtain the target compound 2-4{6'-(2-(4-phenylbenzo[4,5]thieno[3,2-d]pyrimidin-2-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-carboxynitrile} (22.4 g, yield 70%).

[0362] Mass spectrometry: [(M+H)] + ]:595.76

[0363] [Synthetic Examples 53 to 55]

[0364] The target compound C was synthesized using intermediates A and B as described in Table 11 below, except that the process was the same as in Synthesis Example 52.

[0365] [Table 11]

[0366]

[0367] [Synthetic Example 56] Synthesis of Compound 2-61

[0368]

[0369] [Synthetic Example 56-1] Synthesis of Compound 2-61-ii

[0370] 100 g (392.0 mmol, 1 eq) of 2,4-dichlorobenzo[4,5]thieno[3,2-d]pyrimidine, 52.6 g (431.2 mmol, 1.1 eq) of phenylboronic acid, 18.1 g (15.7 mmol, 0.04 eq) of Pd(PPh3)4, and 108.3 g (783.9 mmol, 2 eq) of K2CO3 were added to 1500 ml of THF and 500 ml of H2O, and the mixture was heated under reflux and stirred for 6 hours. After the reaction was completed, the mixture was deactivated with sufficient water, then transferred to a separatory funnel, and the organic layer was separated and extracted by MC. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography to obtain the target compound 2-61-ii{2-chloro-4-phenylbenzo[4,5]thieno[3,2-d]pyrimidine} (100.0 g, yield 86%).

[0371] Mass spectrometry: [(M+H)] + ]:296.77

[0372] NMR ( 1 H): σ= 8.05(1H, d), 7.93(1H, d), 7.84(2H, d), 7.53-7.42(5H, m)

[0373] [Synthetic Example 56-2] Synthesis of Compound 2-61-i

[0374] 100.0 g (337.1 mmol, 1 eq) of 2-chloro-4-phenylbenzo[4,5]thieno[3,2-d]pyrimidine, 58.0 g (370.8 mmol, 1.1 eq) of (2-chlorophenyl)boric acid, 11.7 g (10.1 mmol, 0.03 eq) of Pd(PPh3)4, and 93.2 g (674.2 mmol, 2 eq) of K2CO3 were added to 1500 ml of THF and 600 ml of H2O, and the mixture was heated under reflux with stirring for 4 hours. After the reaction was completed, the mixture was deactivated with sufficient water, then transferred to a separatory funnel, and the organic layer was separated and extracted by MC. The extracted organic layer was concentrated, then adsorbed onto silica gel and purified by column chromatography to obtain the target compound 2-61-i{2-(2-chlorophenyl)-4-phenylbenzo[4,5]thiopheno[3,2-d]pyrimidine} (115.6 g, yield 89%).

[0375] Mass spectrometry: [(M+H)] + ]:372.87

[0376] NMR ( 1H): σ= 8.05(1H, d), 7.93(1H, d), 7.84(2H, d), 7.71(1H, d), 7.61-7.38(8H, m)

[0377] [Synthetic Example 56-3] Synthesis of Compound 2-61

[0378] 20 g (53.6 mmol, 1 eq) of 2-(2-chlorophenyl)-4-phenylbenzo[4,5]thieno[3,2-d]pyrimidine, 29.7 g (64.4 mmol, 1.2 eq) of 4-(2'-(4,4,5,5-tetramethyl-1,3,2-dioxaborane-2-yl)spiro[cyclohexane-1,9'-fluorene]-7'-yl)benzyl nitrile, 0.4 g (1.6 mmol, 0.03 eq) of Pd(OAc), 2.6 g (5.4 mmol, 0.1 eq) of XPhos, and 17.8 g (128.7 mmol, 2 eq) of K2CO3 were added to 300 ml of toluene, 80 ml of EtOH, and 80 ml of H2O. The mixture was heated under reflux and stirred for 6 hours. After the reaction was complete, the mixture was deactivated with sufficient water, then transferred to a separatory funnel, and the organic layer was separated and extracted using MC. The extracted organic layer was concentrated, then adsorbed onto silica gel and purified by column chromatography to obtain the target compound 2-61{4-(2'-(2-(4-phenylbenzo[4,5]thieno[3,2-d]pyrimidin-2-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-7'-yl)benzylnitrile} (26.7 g, yield 74%).

[0379] Mass spectrometry: [(M+H)] + ]:671.86

[0380] [Synthetic Examples 57 to 59]

[0381] The target compound D was synthesized using intermediates A, B and C as described in Table 12 below, except that the process was the same as in Synthesis Example 56.

[0382] [Table 12]

[0383]

[0384] [Synthetic Example 60] Synthesis of Compounds 2-77

[0385]

[0386] [Synthetic Example 60-1] Synthesis of Compound 2-77-ii

[0387] 30 g (117.6 mmol, 1 eq) of 2,4-dichlorobenzo[4,5]thieno[3,2-d]pyrimidine, 18.4 g (117.6 mmol, 1.0 eq) of (2-chlorophenyl)boric acid, 5.4 g (4.7 mmol, 0.04 eq) of Pd(PPh3)4, and 32.5 g (235.2 mmol, 2 eq) of K2CO3 were added to 450 ml of THF and 150 ml of H2O, and the mixture was heated under reflux and stirred for 5 hours. After the reaction was completed, the mixture was deactivated with sufficient water, then transferred to a separatory funnel, and the organic layer was separated and extracted by MC. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography to obtain the target compound 2-77-ii{2-chloro-4-(2-chlorophenyl)benzo[4,5]thieno[3,2-d]pyrimidine} (31.2 g, yield 80%).

[0388] Mass spectrometry: [(M+H)] + ]:331.21

[0389] NMR ( 1 H): σ= 8.05(1H, d), 7.93(1H, d), 7.71(1H, d), 7.61(1H, d), 7.49-7.38(4H, m)

[0390] [Synthetic Example 60-2] Synthesis of Compound 2-77-i

[0391] 31.2 g (94.1 mmol, 1 eq) of 2-chloro-4-(2-chlorophenyl)benzo[4,5]thieno[3,2-d]pyrimidine, 22.4 g (112.9 mmol, 1.2 eq) of [1,1'-biphenyl]-4-ylboronic acid, 3.3 g (2.8 mmol, 0.03 eq) of Pd(PPh3)4, and 26.0 g (188.1 mmol, 2 eq) of K2CO3 were added to 450 ml of THF and 150 ml of H2O, and the mixture was heated under reflux with stirring for 4 hours. After the reaction was completed, the mixture was deactivated with sufficient water, then transferred to a separatory funnel, and the organic layer was separated and extracted by MC. The extracted organic layer was concentrated, then adsorbed onto silica gel and purified by column chromatography to obtain the target compound 2-77-i{2-([1,1'-biphenyl]-4-yl)-4-(2-chlorophenyl)benzo[4,5]thiopheno[3,2-d]pyrimidine} (37.2 g, yield 88%).

[0392] Mass spectrometry: [(M+H)] + ]:448.97

[0393] NMR ( 1H): σ= 8.05(1H, d), 7.96-7.93(3H, m), 7.75(2H, d), 7.71(1H, d),7.61(1H, d), 7.49-7.38(7H, m), 7.25(2H, d)

[0394] [Synthetic Example 60-3] Synthesis of Compound 2-77

[0395] 20 g (44.5 mmol, 1 eq) of 2-([1,1'-biphenyl]-4-yl)-4-(2-chlorophenyl)benzo[4,5]thieno[3,2-d]pyrimidine, 20.6 g (53.5 mmol, 1.2 eq) of 6'-(4,4,5,5-tetramethyl-1,3,2-dioxaborane-2-yl)spiro[cyclohexane-1,9'-fluorene]-2'-formonitrile, 0.3 g (1.3 mmol, 0.03 eq) of Pd(OAc), 2.1 g (4.5 mmol, 0.1 eq) of XPhos, and 14.8 g (106.9 mmol, 2 eq) of K2CO3 were added to 300 ml of toluene, 80 ml of EtOH, and 80 ml of H2O. The mixture was heated to reflux and stirred for 6 hours. After the reaction was completed, the compound was deactivated using sufficient water, then transferred to a separatory funnel, and MC was added to separate and extract the organic layer. The extracted organic layer was concentrated, adsorbed onto silica gel, and purified by column chromatography to obtain the target compound 2-77{6'-(2-(2-([1,1'-biphenyl]-4-yl)benzo[4,5]thieno[3,2-d]pyrimidin-4-yl)phenyl)spiro[cyclohexane-1,9'-fluorene]-2'-formonitrile} (22.7 g, yield 76%).

[0396] Mass spectrometry: [(M+H)] + ]:671.86

[0397] [Synthetic Examples 61 to 63]

[0398] The target compound D was synthesized using intermediates A, B and C as described in Table 13 below, except that the process was the same as in Synthesis Example 60.

[0399] [Table 13]

[0400]

[0401] [Example 1] Fabrication of a blue organic electroluminescent element

[0402] After the compound 1-1 synthesized in the above synthesis example was purified to high purity by sublimation using a commonly known method, a blue organic electroluminescent element was fabricated according to the following process.

[0403] First, a glass substrate coated with an indium tin oxide (ITO) film at a thickness of 1200 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. Finally, the substrate was transferred to a vacuum evaporation machine.

[0404] An organic electroluminescent element was fabricated by stacking the following compounds on the prepared ITO transparent electrode in the following order: 98wt% HI + 2wt% HAT-CN6 (10nm) / HI (140nm) / EB (5nm) / 98wt% BH + 2wt% BD (20nm) / compound 1-1 + Liq (1:1 weight ratio) (30nm) / LiF (1nm) / Al (100nm). The structures of HI, HAT-CN6, EB, BH, BD, and Liq used are as follows.

[0405]

[0406] [Examples 2 to 63] Fabrication of Blue Organic Electroluminescent Element

[0407] The blue organic electroluminescent element was fabricated in the same manner as in Example 1, except that the compounds listed in Table 14 were used instead of compounds 1-1 used as electron transport layer materials in Example 1.

[0408] [Comparative Examples 1 to 8] Fabrication of Blue Organic Electroluminescent Element

[0409] Alq3 and compounds E-1 to E-7 were used respectively to replace compound 1-1, which was used as the electron transport layer material in Example 1, and the same procedure as in Example 1 was followed to fabricate a blue organic electroluminescent element. The structures of Alq3 and compounds E-1 to E-7 used in this case are shown below.

[0410]

[0411] [Evaluation Example 1]

[0412] The current density of the organic electroluminescent elements manufactured in Examples 1 to 63 and Comparative Examples 1 to 8 was measured to be 10 mA / cm². 2 The driving voltage, emission wavelength, and current efficiency are shown in Table 14 below.

[0413] [Table 14]

[0414]

[0415]

[0416] As can be seen from Table 14 above, the organic light-emitting elements (OLEDs) manufactured in Examples 1 to 63 exhibit superior driving voltage, emission peak, and current efficiency compared to those manufactured in Comparative Examples 1 to 8. In particular, it can be demonstrated that the compounds of the present invention contain a condensed heteroaromatic ring moiety formed by the fusion of a monocyclic nitrogen-containing heteroaromatic ring (e.g., a pyrimidine ring) and a benzo[a]cyclic ring (e.g., a benzofuran ring). Compared to the OLEDs of Comparative Examples 2 to 3, which used compounds containing a monocyclic azazinyl group (e.g., a pyridyl group) or a quinolinyl group (e.g., Compound E-1, Compound E-2) as electron transport layer materials, the OLEDs of Examples 1 to 63, which used such compounds of the present invention as electron transport layer materials, exhibit superior driving voltage and current efficiency. In particular, it can be demonstrated that the improvement in driving voltage of the elements in Examples 1 to 63 is significant compared to those in Comparative Examples 2 to 3. This is because the monocyclic nitrogen-containing heteroaromatic ring (e.g., pyrimidine ring) in the condensed heteroaromatic ring portion of the compound has a wider conjugated region, thus there are relatively more electrons distributed in the condensed heteroaromatic ring portion, resulting in excellent initial driving voltage and overall charge transport.

[0417] Furthermore, the condensed heteroaromatic ring moiety of the compounds of the present invention has relatively more electrons compared to a typical dibenzofuran group, and therefore can act as an electron loading gate (EWG), thereby improving the electron injection and transport characteristics of the compounds. Therefore, it can be seen that, compared to Comparative Example 4, which uses a compound containing a dibenzofuran group (e.g., ET-3) as an electron transport layer material, the elements in Examples 1-63, which use the compounds of the present invention as electron transport layer materials, are effective in improving both driving voltage and current efficiency.

[0418] Furthermore, the compounds of the present invention, due to the substitution of one side of the spiro[cyclohexane-1,9'-fluorene] moiety with a cyano group, can improve the interaction with the adjacent cathode, thereby enhancing electron injection characteristics. Moreover, they can also increase initial charge generation, thereby allowing more electrons to be obtained from the cathode and transported to the light-emitting layer. Therefore, compared to Comparative Example 5, which uses a compound with an unsubstituted condensation moiety (e.g., ET-4), the devices using the compounds of the present invention in Examples 1-63 can improve luminous efficiency while increasing the initial driving voltage. In addition, since the dipole moment of the compounds of the present invention is increased due to the substituted cyano group, the deposition between the electrode and the organic material can be increased, minimizing defects within the device.

[0419] Furthermore, the condensed heteroaromatic ring moiety and the spiro[cyclohexane-1,9'-fluorene] moiety of the compounds of the present invention are linked by an arylene group as a linking group. Therefore, the spiro[cyclohexane-1,9'-fluorene] moiety, which is a highly electron-donating group (EDG), and the condensed heteroaromatic ring moiety, which is a highly electron-withdrawing group (EWG), are appropriately separated, resulting in LUMO-HOMO orbital separation. This improves the band gap and provides an appropriate LUMO energy. Therefore, it can be seen that, compared to the element in Comparative Example 6 using the compound (DP: ET-5) which does not contain a linking group, the elements in Examples 1-63 using the compounds of the present invention have lower driving voltages and higher current efficiency.

[0420] [Example 64] Fabrication of a blue organic electroluminescent element

[0421] After the compound 1-1 synthesized in the above synthesis example 1 was purified to high purity by sublimation using a commonly known method, a blue organic electroluminescent element was fabricated according to the following process.

[0422] First, a glass substrate coated with an indium tin oxide (ITO) film at a thickness of 1200 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. Finally, the substrate was transferred to a vacuum evaporation machine.

[0423] An organic electroluminescent element was fabricated by stacking the following compounds on the prepared ITO transparent electrode in the following order: 98wt% HI + 2wt% HAT-CN6 (10nm) / HI (140nm) / EB (5nm) / 98wt% BH + 2wt% BD (20nm) / Compound 1-1 (5nm) / ET + Liq (1:1 weight ratio) (30nm) / LiF (1nm) / Al (100nm). The structures of HI, HAT-CN6, EB, BH, BD, ET, and Liq used are as follows.

[0424]

[0425] [Examples 65 to 126] Fabrication of Blue Organic Electroluminescent Element

[0426] The blue organic electroluminescent element was fabricated in the same manner as in Example 65, except that the compounds listed in Table 15 below were used instead of compounds 1-1 used as electron transport auxiliary layer materials in Example 64.

[0427] [Comparative Example 9] Fabrication of a Blue Organic Electroluminescent Element

[0428] The blue organic electroluminescent element was fabricated in the same manner as in Example 65, except that compound 1-1, which was used as an electron transport auxiliary layer material in Example 64, was not used.

[0429] [Comparative Examples 10 to 16] Fabrication of Blue Organic Electroluminescent Element

[0430] The blue organic electroluminescent element was fabricated in the same manner as in Example 64, except that compounds E-1 to E-7 were used instead of compound 1-1, which was used as the electron transport auxiliary layer material in Example 64. The structures of compounds E-1 to E-7 used in this case are as follows.

[0431]

[0432] [Evaluation Example 2]

[0433] The current density of the organic electroluminescent elements manufactured in Examples 64 to 126 and Comparative Examples 10 to 16 was measured to be 10 mA / cm². 2 The driving voltage, emission wavelength, and current efficiency are shown in Table 15 below.

[0434] [Table 15]

[0435]

[0436]

[0437] As can be seen from Table 15 above, the organic light-emitting elements manufactured in Examples 64 to 126 exhibit superior driving voltage, emission peak, and current efficiency compared to those manufactured in Comparative Examples 9 to 16. Furthermore, it is evident that when the compounds of the present invention are applied to the electron transport layer, the driving voltage of the element is improved, and when the compounds of the present invention are applied to the electron transport auxiliary layer, the efficiency of the element is significantly improved.

[0438] In particular, it can be seen that, compared with the device of Comparative Example 7 which does not contain an electron transport auxiliary layer, the driving voltage and current efficiency of the devices in Examples 64-126, in which the compound of the present invention is applied to the electron transport auxiliary layer, are both improved. Therefore, it can be seen that the compound of the present invention helps to improve the current efficiency of the device by confining excitons within the light-emitting layer. Furthermore, the compound of the present invention, due to its excellent electron transport properties, exhibits excellent electron transfer capability from the electron transport layer to the light-emitting layer, thus also improving the driving voltage of the device.

[0439] Furthermore, compared to the devices in Comparative Examples 9-16 that used compounds E-1 to E-7 respectively, the devices in Examples 64-126 that applied the compounds of the present invention to the electron transport auxiliary layer exhibited superior driving voltage and current efficiency. Therefore, it can be concluded that the compounds of the present invention have superior electron transfer capabilities compared to compounds E-1 to E-7.

Claims

1. A compound represented by the following chemical formula 1: [Chemical Formula 1] In the chemical formula 1, X1 to X4 may be the same as or different from each other, and each is independently N or C(Ar1), where, At least two of X1 to X4 are N; Y1 is selected from the group consisting of O, S, Se, C(Ar2)(Ar3) and N(Ar4). a is 1 or 2. b is an integer from 0 to 4. R1, R2, and Ar1 to Ar4 may be the same as or different from each other, and are each independently selected from hydrogen, deuterium (D), halogen group, cyano group, nitro group, amino group, hydroxyl group, C1~C4. 40 Alkyl groups, C2~C 40 alkenyl, C2~C 40 alkynyl group, C3~C 40 Cycloalkyl groups, heterocyclic alkyl groups with 3 to 40 nuclei, C6~C 60 aryl, heteroaryl with 5 to 60 nuclei, C1~C 40 alkoxy groups, C6~C 60 aryloxy groups, C1~C 40 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; n is an integer from 1 to 4. L1 is C6~C 18 Alpha-aryl, The alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, alkoxy, aryloxy, alkylsilyl, arylsilyl, alkylboryl, arylboryl, arylphosphinyl, arylphosphine oxide, and arylamino groups of R1, R2, and Ar1 to Ar4, as well as the arylene group of L1, are each independently selected from deuterium (D), halogen, cyano, nitro, amino, hydroxyl, C1-C4. 40 Alkyl groups, C2~C 40 alkenyl, C2~C 40 alkynyl group, C3~C 40 Cycloalkyl groups, heterocyclic alkyl groups with 3 to 40 nuclei, C6~C 60 aryl groups, heteroaryl groups with 5 to 60 nuclei, C1~C 40 alkoxy groups, C6~C 60 aryloxy groups, C1~C 40 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.

2. The compound according to claim 1, wherein... Select the group consisting of the following parts Mo1-1 to Mo1-34: Of the portions Mo1-1 to Mo1-34, Y1, b, R1, and R2 are each identical to their definitions in claim 1. b1 is an integer from 0 to 3.

3. The compound according to claim 1, wherein two of X1 to X4 are N.

4. The compound according to claim 1, wherein L1 is selected from the group consisting of the following linking groups L1-1 to L1-11: Among the linking groups L1-1 to L1-11, c is an integer from 0 to 4. d is an integer from 0 to 6. e is an integer from 0 to 8. f is an integer from 0 to 7. g is an integer from 0 to 3. h is an integer from 0 to 5. i is an integer from 0 to 10. Multiple Rs may be the same or different from each other. R is selected from deuterium (D), halogen, cyano, nitro, amino, hydroxyl, C1~C1. 40 Alkyl groups, C2~C 40 alkenyl, C2~C 40 alkynyl group, C3~C 40 Cycloalkyl groups, heterocyclic alkyl groups with 3 to 40 nuclei, C6~C 60 aryl groups, heteroaryl groups with 5 to 60 nuclei, C1~C 40 alkoxy groups, C6~C 60 aryloxy groups, C1~C 40 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 compound according to claim 1, wherein the compound represented by chemical formula 1 is represented by any one of the following chemical formulas 2 to 9: [Chemical Formula 2] [Chemical Formula 3] [Chemical Formula 4] [Chemical Formula 5] [Chemical Formula 6] [Chemical Formula 7] [Chemical Formula 8] [Chemical Formula 9] Among the chemical formulas 2 to 9, X1 to X4, Y1, a, b, R1, R2, n, and L1 are each identical to the definitions in claim 1. b1 is an integer from 0 to 3.

6. The compound according to claim 1, wherein the compound represented by chemical formula 1 is represented by chemical formula 10 or 11: [Chemical Formula 10] [Chemical Formula 11] In the chemical formulas 10 and 11, X1 to X4, Y1, a, b, R1, and R2 are each identical to the definitions in claim 1. b1 is an integer from 0 to 3.

7. The compound according to claim 1, wherein the compound represented by chemical formula 1 is represented by any one of the following chemical formulas 12 to 15: [Chemical Formula 12] [Chemical Formula 13] [Chemical Formula 14] [Chemical Formula 15] In the chemical formulas 12 to 15, Y1, b, R2, and n are each the same as defined in claim 1. Multiple R1s may be the same or different from each other. R1 can be chosen freely from C6 to C. 60 The group consists of aryl groups and heteroaryl groups with 5 to 60 nuclei. The aryl and heteroaryl groups of R1 are each independently selected from deuterium (D), halogen, cyano, nitro, amino, hydroxyl, C1~C1. 40 Alkyl, C6~C 60 aryl groups, heteroaryl groups with 5 to 60 nuclei, and C6~C6 groups. 60 One or more substituents in the group consisting of arylamine groups are substituted or unsubstituted, and when there are multiple substituents, they may be the same as or different from each other. b1 is an integer from 0 to 3.

8. The compound according to claim 1, wherein the compound represented by chemical formula 1 is selected from the group consisting of: 。 9. 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 layer comprises the compound according to any one of claims 1 to 8.

10. The organic electroluminescent element according to claim 9, wherein the organic layer containing the compound is an electron transport layer or an electron transport auxiliary layer.

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