Organic compound and organic electroluminescence device using the same

Abstract

The present invention relates to a novel organic compound and an organic electroluminescence device using the same, and more particularly to a compound having excellent electron injection and transport capabilities, and an organic electroluminescence device having improved progressive driving voltage characteristics as well as properties such as luminous efficiency, driving voltage, and long life by incorporating the compound in one or more organic layers.

Description

[Technical field]

[0001] The present invention relates to a novel organic compound and an organic electroluminescence device using the same, and more particularly to a compound having excellent electron transport ability, and an organic electroluminescence device having improved properties such as luminous efficiency, driving voltage, and long life by incorporating the compound in one or more organic layers. [Background technology]

[0002] In an organic electroluminescence element (hereinafter referred to as "organic EL element"), when a voltage is applied between the two electrodes, holes are injected from the anode and electrons are injected from the cathode into the organic layer. The injected holes and electrons combine to form excitons (excitoN), which emit light when they return to the ground state. The materials used in the organic layer are classified according to their functions into light-emitting materials, hole-injecting materials, hole-transporting materials, electron-transporting materials, electron-injecting materials, etc.

[0003] The materials forming the light-emitting layer of an organic EL device are classified into blue, green, and red light-emitting materials according to the color of the light emitted. In addition, yellow and orange light-emitting materials may be used as light-emitting materials to realize better natural colors. In addition, host-dopant-based light-emitting materials are used as light-emitting materials to improve color purity and improve luminous efficiency by energy transfer. Dopant materials are divided into fluorescent dopants using organic materials and phosphorescent dopants using metal complex compounds containing heavy atoms such as Ir and Pt. Theoretically, such phosphorescent materials can improve luminous efficiency by four times compared to fluorescence, and the development of phosphorescent host materials as well as phosphorescent dopants is attracting attention.

[0004] To date, NPB, BCP, Alq, and ZnO have been used for the hole injection layer, hole transport layer, hole blocking layer, and electron transport layer. 3As for luminescent materials, anthracene derivatives have been reported as fluorescent dopant-host materials. In particular, phosphorescent materials that have great merits in terms of improving efficiency among luminescent materials include Firpic and Ir(ppy). 3 , (acac)Ir(btp) 2 Metal complex compounds containing Ir, such as the above, are used as blue, green, and red dopant materials. Currently, CBP shows excellent properties as a phosphorescent host material.

[0005] However, although conventional organic layer materials are advantageous in terms of light-emitting properties, they have low glass transition temperatures and poor thermal stability, and therefore are not satisfactory in terms of the life span of organic EL devices. Therefore, there is a demand for the development of organic layer materials with excellent performance. Summary of the Invention [Problem to be solved by the invention]

[0006] An object of the present invention is to provide a novel organic compound which is excellent in electron injection and transport ability, electrochemical stability, thermal stability, etc., and can be used as an organic layer material of an organic EL device, specifically, as an electron transport layer material or an N-type charge generation layer material.

[0007] Another object of the present invention is to provide an organic EL element that exhibits a low driving voltage, high luminous efficiency, and an improved lifespan by incorporating the novel organic compound described above. [Means for solving the problem]

[0008] In order to achieve the above object, the present invention provides an organic compound represented by the following chemical formula 1: [ka] (In the formula, n is an integer from 0 to 3, L 1 is a direct bond, or C 6 ~C 60and heteroarylene groups having 5 to 60 ring atoms, Ar 1 is hydrogen, deuterium (D), halogen group, cyano group, nitro group, amino group, C 1 ~C 40 Alkyl groups of C 2 ~C 40 Alkenyl group, C 2 ~C 40 Alkynyl groups, C 3 ~C 40 Cycloalkyl groups having 3 to 40 ring atoms, heterocycloalkyl groups having 3 to 40 ring atoms, C 6 ~C 60 aryl groups, heteroaryl groups with 5 to 60 ring atoms, C 1 ~C 40 Alkyloxy groups, C 6 ~C 60 Aryloxy groups, C 1 ~C 40 Alkylsilyl group, C 6 ~C 60 Arylsilyl groups, C 1 ~C 40 Alkylboron group, C 6 ~C 60 Arylboron groups, C 6 ~C 60 Arylphosphine groups, C 6 ~C 60 Arylphosphine oxide group, C 6 ~C 60 and C 2 ~C 40 C substituted with an alkenyl group 6 ~C 60 or which join adjacent groups to form a fused ring; The above L 1 Arylene and heteroarylene groups of the above formula: 1The alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, arylboron group, arylphosphine group, arylphosphine oxide group, arylamine group, aryl group substituted with an alkenyl group, and fused ring each independently represent deuterium, halogen, cyano group, nitro group, C 2 ~C 40 Alkenyl group, C 2 ~C 40 Alkynyl groups, C 3 ~C 40 Cycloalkyl groups having 3 to 40 ring atoms, heterocycloalkyl groups having 3 to 40 ring atoms, C 1 ~C 40 Alkyl groups of C 6 ~C 60 aryl groups, heteroaryl groups with 5 to 60 ring atoms, C 1 ~C 40 Alkyloxy groups, C 6 ~C 60 Aryloxy groups, C 1 ~C 40 Alkylsilyl group, C 6 ~C 60 Arylsilyl groups, C 1 ~C 40 Alkylboron group, C 6 ~C 60 Arylboron groups, C 6 ~C 60 Arylphosphine groups, C 6 ~C 60 and C 6 ~C 60 The arylamine group may be substituted or unsubstituted with one or more substituents selected from the group consisting of the following arylamine groups:

[0009] The present invention also provides an organic EL device comprising an anode, a cathode, and one or more organic layers interposed between the anode and the cathode, at least one of which contains the organic compound described above. In this case, the organic layer containing the compound may be an electron transport layer.

[0010] The present invention also provides an organic EL device comprising: an anode and a cathode spaced apart from each other; a plurality of light-emitting units interposed between the anode and the cathode; and an N-type charge generation layer and a P-type charge generation layer interposed between adjacent light-emitting units, each of the light-emitting units including a hole transport layer, a light-emitting layer, and an electron transport layer, and the N-type charge generation layer comprises the organic compound described above. Effect of the Invention

[0011] The compound of the present invention is excellent in electron transport ability, light emitting ability, electrochemical stability, thermal stability, etc., and can be used as an organic layer material of an organic EL device. In particular, when the compound of the present invention is used as at least one of an electron transport layer material, an electron transport auxiliary layer material, and an N-type charge generation layer material, an organic EL device having superior light emitting performance, low driving voltage, high efficiency, and long life characteristics compared to conventional materials can be manufactured, and a full-color display panel with improved performance and life can also be manufactured. [Brief description of the drawings]

[0012] [Figure 1] 1 is a cross-sectional view illustrating an organic EL element according to a first embodiment of the present invention. [Diagram 2] FIG. 4 is a cross-sectional view illustrating an organic EL element according to a second embodiment of the present invention. [Diagram 3] FIG. 11 is a cross-sectional view illustrating an organic EL element according to a third embodiment of the present invention. [Figure 4] FIG. 11 is a cross-sectional view illustrating an organic EL element according to a fourth embodiment of the present invention. [Explanation of symbols]

[0013] 100: anode, 200: cathode, 300: organic layer, 310: hole injection layer, 320: hole transport layer, 330: light emitting layer, 340: Electron transport layer, 350: Electron injection layer, 360: electron transport auxiliary layer, 400: first light-emitting unit, 410: first hole transport layer; 420: first light emitting layer; 430: first electron transport layer; 440: hole injection layer; 500: second light-emitting unit; 510: second hole transport layer; 520: second light-emitting layer; 530: second electron transport layer; 600: charge generating layer, 610: N-type charge generating layer, 620: P-type charge generation layer DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0014] The present invention will be described in detail below.

[0015] <New Compound> The compound according to the present invention includes a basic structure in which a pyridine moiety is bonded to the 5-carbon position of a phenanthridine moiety, and various substituents such as an aryl group and a heteroaryl group (particularly, EWG) are bonded to the pyridine moiety, and is represented by the above Chemical Formula 1. The compound of the present invention, which is represented by the above Chemical Formula 1, has excellent electron injection and transport capabilities, electrochemical stability, thermal stability, etc., and therefore provides a novel compound that can be used as an electron transport layer material, an electron transport auxiliary layer material, or an N-type charge generation layer material, which can improve the efficiency, long life, driving voltage characteristics, and progressive driving voltage characteristics of an organic EL device. The carbon and nitrogen position numbers of the phenanthridine moiety can be represented as follows: [ka]

[0016] Specifically, in the compound represented by the above formula 1, a pyridine moiety is bonded to the carbon position at the 5th position of the phenanthridine moiety. In this case, the bond position of the pyridine moiety with the phenanthridine moiety is the ortho position of nitrogen (N). The compound of the present invention having such a structure is capable of metal binding. As a result, the compound of the present invention can form a gap state by binding with metals such as alkali metals and alkaline earth metals, which are dopants in the N-type charge generation layer, and when used as an N-type charge generation layer material, the electron transfer characteristics from the N-type charge generation layer to the electron transport layer are improved. In addition, when the compound of the present invention is used as an N-type charge generation layer material, it can prevent the alkali metals and alkaline earth metals from diffusing to the P-type charge generation layer by binding with the alkali metals or alkaline earth metals in the N-type charge generation layer. Therefore, when the compound of the present invention is used as an N-type charge generation layer material, the performance and life of the organic EL device can be improved.

[0017] As described above, the compound represented by Chemical Formula 1 according to the present invention has excellent electron injection and transport capabilities. Therefore, the compound of the present invention can be used as an organic layer, preferably an electron transport layer material, of an organic EL device. The compound of the present invention can also be used as an N-type charge generation layer material of an organic EL device having a tandem structure. In this way, when the compound represented by Chemical Formula 1 according to the present invention is used as an electron transport layer material or an N-type charge generation layer material of an organic EL device, the characteristics such as the driving voltage, luminous efficiency, and life of the device are improved, and the increase in the progressive driving voltage can be prevented, thereby maximizing the performance of a full-color organic light-emitting panel using the organic EL device.

[0018] In the compound represented by the above Chemical Formula 1, n is an integer of 0 to 3, and specifically, can be an integer of 0 to 2.

[0019] Here, if n is 0, then L 1 means a direct bond (single bond). When n is an integer of 1 to 3, L1 is a divalent linker group, C 6 ~C 30 and heteroarylene groups having 5 to 30 ring atoms, specifically, 6 ~C 18 and heteroarylene groups having 5 to 18 ring atoms. 1 may be the same or different from each other.

[0020] The above L 1 The arylene group and the heteroarylene group each independently represent a deuterium atom, a halogen atom, a cyano group, a nitro group, C 2 ~C 40 Alkenyl group, C 2 ~C 40 Alkynyl groups, C 3 ~C 40 Cycloaryl groups, heterocycloalkyl groups having 3 to 40 ring atoms, C 1 ~C 40 Alkyl groups of C 6 ~C 60 aryl groups, heteroaryl groups with 5 to 60 ring atoms, C 1 ~C 40 Alkyloxy groups, C 6 ~C 60 Aryloxy groups, C 1 ~C 40 Alkylsilyl group, C 6 ~C 60 Arylsilyl groups, C 1 ~C 40 Alkylboron group, C 6 ~C 60 Arylboron groups, C 6 ~C 60 Arylphosphine groups, C 6 ~C 60 and C 6 ~C 60 The arylamine groups may be substituted or unsubstituted with one or more substituents selected from the group consisting of arylamine groups, specifically, each independently represents a deuterium atom, a halogen atom, a cyano group, a nitro group, C 1 ~C40 Alkyl groups of C 2 ~C 40 Alkenyl group, C 2 ~C 40 Alkynyl groups, C 3 ~C 40 Cycloalkyl groups having 3 to 40 ring atoms, heterocycloalkyl groups having 3 to 40 ring atoms, C 6 ~C 60 and heteroaryl groups having 5 to 60 ring atoms. In this case, when there are a plurality of the above-mentioned substituents, they may be the same or different.

[0021] In one example, [ka] can be a linker group represented by any one of the following chemical formulas L1 to L5. [ka] [ka] [ka] [ka] [ka] In the above chemical formulas L1 to L5, n1 and n2 each represent an integer of 0 to 3, provided that 0≦n1+n2≦3; l is an integer from 0 to 4; m is an integer from 0 to 3; Multiple R a may be the same or different from each other, R a is hydrogen, deuterium, halogen group, cyano group, nitro group, amino group, C 1 ~C 40 Alkyl groups of C2 ~C 40 Alkenyl group, C 2 ~C 40 Alkynyl groups, C 3 ~C 40 Cycloalkyl groups having 3 to 40 ring atoms, heterocycloalkyl groups having 3 to 40 ring atoms, C 6 ~C 60 aryl groups, heteroaryl groups with 5 to 60 ring atoms, C 1 ~C 40 Alkyloxy groups, C 6 ~C 60 Aryloxy groups, C 1 ~C 40 Alkylsilyl group, C 6 ~C 60 Arylsilyl groups, C 1 ~C 40 Alkylboron group, C 6 ~C 60 Arylboron groups, C 6 ~C 60 Arylphosphine groups, C 6 ~C 60 and C 6 ~C 60 and specifically, hydrogen, deuterium, a cyano group, C 1 ~C 40 Alkyl groups of C 2 ~C 40 Alkenyl group, C 2 ~C 40 Alkynyl groups, C 3 ~C 40 Cycloalkyl groups having 3 to 40 ring atoms, heterocycloalkyl groups having 3 to 40 ring atoms, C 6 ~C 60 aryl groups, heteroaryl groups having 5 to 60 ring atoms, and C 6 ~C 60 The aryl amine groups are selected from the group consisting of:

[0022] In another example, L 1 can be a direct bond or any one of the linker groups L-1 to L-51 below. [ka] [ka] [ka] [ka] In the above linker groups L-1 to L-51, * is a binding site to Chemical Formula 1 above, Multiple 1's may be the same or different, A plurality of m's may be the same or different, l is an integer from 0 to 4; m is an integer from 0 to 3; Multiple R a may be the same or different from each other, R a is hydrogen, deuterium, halogen, cyano group, nitro group, C 2 ~C 40 Alkenyl group, C 2 ~C 40 Alkynyl groups, C 3 ~C 40 Cycloalkyl groups having 3 to 40 ring atoms, heterocycloalkyl groups having 3 to 40 ring atoms, C 1 ~C 40 Alkyl groups of C 6 ~C 60 aryl groups, heteroaryl groups with 5 to 60 ring atoms, C 1 ~C 40 Alkyloxy groups, C 6 ~C 60 Aryloxy groups, C 1 ~C 40 Alkylsilyl group, C 6 ~C 60 Arylsilyl groups, C 1 ~C 40 Alkylboron group, C 6 ~C 60 Arylboron groups, C 6 ~C 60 Arylphosphine groups, C 6 ~C 60and C 6 ~C 60 Specifically, the arylamine group is selected from the group consisting of hydrogen, deuterium, halogen, cyano group, nitro group, C 1 ~C 12 Alkyl groups of C 6 ~C 10 and heteroaryl groups having 5 to 10 ring atoms.

[0023] Depending on the bonding position of L1, the compound represented by Chemical Formula 1 above may be a compound represented by Chemical Formulas 2 to 5 below, but is not limited thereto. [ka] [ka] [ka] In the above Chemical Formula 2 to Chemical Formula 4, n, L 1 , and Ar 1 is as defined in Chemical Formula 1 above.

[0024] In addition, in the compound represented by the above chemical formula 1, Ar 1 is hydrogen, deuterium, halogen group, cyano group, nitro group, amino group, C 1 ~C 40 Alkyl groups of C 2 ~C 40 Alkenyl group, C 2 ~C 40 Alkynyl groups, C 3 ~C 40 Cycloalkyl groups having 3 to 40 ring atoms, heterocycloalkyl groups having 3 to 40 ring atoms, C 6 ~C 60 aryl groups, heteroaryl groups with 5 to 60 ring atoms, C 1 ~C 40 Alkyloxy groups, C 6 ~C 60 Aryloxy, C 1 ~C 40Alkylsilyl group, C 6 ~C 60 Arylsilyl groups, C 1 ~C 40 Alkylboron group, C 6 ~C 60 Arylboron groups, C 6 ~C 60 Arylphosphine groups, C 6 ~C 60 Arylphosphine oxide group, C 6 ~C 60 and C 2 ~C 40 C substituted with an alkenyl group 6 ~C 60 or an adjacent group (e.g., Ar 1 -L 1 ) to form a condensed ring, specifically, hydrogen, deuterium, halogen, cyano group, nitro group, C 1 ~C 40 Alkyl groups of C 2 ~C 40 Alkenyl group, C 2 ~C 40 Alkynyl groups, C 3 ~C 40 Cycloalkyl groups having 3 to 40 ring atoms, heterocycloalkyl groups having 3 to 40 ring atoms, C 6 ~C 60 aryl groups, heteroaryl groups having 5 to 60 ring atoms, and C 2 ~C 40 C substituted with an alkenyl group 6 ~C 60 or an adjacent group (e.g., Ar 1 -L 1 ) to form a condensed ring, more specifically, deuterium, cyano group, C 1 ~C 20 Alkyl groups of C 3 ~C 20 Cycloalkyl groups having 3 to 20 ring atoms, heterocycloalkyl groups having 3 to 20 ring atoms, C 6 ~C 30 aryl groups, heteroaryl groups having 5 to 30 ring atoms, and C 2 ~C20 C substituted with an alkenyl group 6 ~C 30 or an adjacent group (e.g., Ar 1 -L 1 ) to form a condensed ring. 3 ~C 60 Condensed aliphatic rings (specifically, C 3 ~C 30 (condensed aliphatic ring), C 6 ~C 60 Condensed aromatic rings (specifically, C 6 ~C 30 fused aromatic rings), 5-60 membered fused aromatic rings containing one or more heteroatoms (e.g., N, O, S, Se, etc.) (specifically, 5-30 membered fused aromatic rings containing one or more heteroatoms), C 3 ~C 60 and combinations thereof.

[0025] In one example, Ar 1 may be a substituent represented by any one selected from the group consisting of the following formulas S1 to S12, but is not limited thereto. In particular, Ar 1 When Ar is an electron withdrawing group (EWG) with high electron withdrawing properties such as S1 and S2 below, the compound of the present invention can be used as an electron transport layer material because the LUMO level can be adjusted to be similar to other electron transport layer materials. 1 When the compound of the present invention, in which is EWG, is used as an N-type charge generating layer material, the difference in LUMO level with the adjacent electron transporting layer is reduced, and the performance of the organic EL device can be greatly improved. [ka] In the above formulas S1 to S12, * is a binding site to Chemical Formula 1 above, Y 1 ~Y 5may be the same or different, and each independently represents N or C(R 1 ), where Y 1 ~Y 5 At least one of C(R 1 ) is multiple, multiple R 1 may be the same or different from each other, Y 6 ~Y 9 may be the same or different, and each independently represents N, N(R 2 ), C(R 3 ), or C(R 4 )(R 5 ), where Y 6 ~Y 9 At least one of the following is N or N(R 2 ), where C(R 2 ) is multiple, multiple R 2 may be the same or different from each other, and C(R 3 ) is multiple, multiple R 3 may be the same or different from each other, and C(R 4 )(R 5 ) is multiple, multiple R 4 may be the same or different, and multiple R 5 may be the same or different, R 4 and R 5 may be the same or different from each other, Y 10 and Y 11 are O or S, Ring Q is a benzene ring; x and y are each 0 or 1; a, d, and e each represent an integer from 0 to 9; b and c are each an integer of 0 to 7, f, h, and i are each an integer of 0 to 4; g is an integer from 0 to 5; j is an integer from 0 to 3; k is an integer from 0 to 8; R 1 ~R 5 , and R S may be the same or different, and each independently represents hydrogen, deuterium, a halogen group, a cyano group, a nitro group, an amino group, C 1 ~C 40 Alkyl groups of C 2 ~C 40 Alkenyl group, C 2 ~C 40 Alkynyl groups, C 3 ~C 40 Cycloalkyl groups having 3 to 40 ring atoms, heterocycloalkyl groups having 3 to 40 ring atoms, C 6 ~C 60 aryl groups, heteroaryl groups with 5 to 60 ring atoms, C 1 ~C 40 Alkyloxy groups, C 6 ~C 60 Aryloxy groups, C 1 ~C 40 Alkylsilyl group, C 6 ~C 60 Arylsilyl groups, C 1 ~C 40 Alkylboron group, C 6 ~C 60 Arylboron groups, C 6 ~C 60 Arylphosphine groups, C 6 ~C 60 and C 6 ~C 60 or an adjacent group (e.g., R 1 -R 1 , R 2 -R 2 , R 2 -R 3 , R 3 -R 3 , R 4 -R 5 etc.) to form a condensed ring, and specifically, each independently represents hydrogen, deuterium, a halogen, a cyano group, a nitro group, C 1 ~C 40 Alkyl groups of C 2 ~C40 Alkenyl group, C 2 ~C 40 Alkynyl groups, C 3 ~C 40 Cycloalkyl groups having 3 to 40 ring atoms, heterocycloalkyl groups having 3 to 40 ring atoms, C 6 ~C 60 or an adjacent group (e.g., R 1 -R 1 , R 2 -R 2 , R 2 -R 3 , R 3 -R 3 , R 4 -R 5 ) to form a condensed ring, more specifically, deuterium, cyano group, C 1 ~C 20 Alkyl groups of C 3 ~C 20 Cycloalkyl groups having 3 to 20 ring atoms, heterocycloalkyl groups having 3 to 20 ring atoms, C 6 ~C 30 and heteroaryl groups having 5 to 30 ring atoms, or an adjacent group (e.g., R 1 -R 1 , R 2 -R 2 , R 2 -R 3 , R 3 -R 3 , R 4 -R 5 etc.) to form a condensed ring, Above R 1 ~R 5 , and R S The alkyl group, the alkenyl group, the alkynyl group, the cycloalkyl group, the heterocycloalkyl group, the aryl group, the heteroaryl group, the alkyloxy group, the aryloxy group, the alkylsilyl group, the arylsilyl group, the alkylboron group, the arylboron group, the arylphosphine group, the arylphosphine oxide group, the arylamine group, and the fused ring each independently represent a deuterium atom, a halogen atom, a cyano group, a nitro group, a C 2 ~C 40Alkenyl group, C 2 ~C 40 Alkynyl groups, C 3 ~C 40 Cycloalkyl groups having 3 to 40 ring atoms, heterocycloalkyl groups having 3 to 40 ring atoms, C 1 ~C 40 Alkyl groups of C 6 ~C 60 aryl groups, heteroaryl groups with 5 to 60 ring atoms, C 1 ~C 40 Alkyloxy groups, C 6 ~C 60 Aryloxy groups, C 1 ~C 40 Alkylsilyl group, C 6 ~C 60 Arylsilyl groups, C 1 ~C 40 Alkylboron group, C 6 ~C 60 Arylboron groups, C 6 ~C 60 Arylphosphine groups, C 6 ~C 60 and C 6 ~C 60 The arylamine groups may be substituted or unsubstituted with one or more substituents selected from the group consisting of arylamine groups, specifically, each independently represents a deuterium atom, a halogen atom, a cyano group, a nitro group, C 1 ~C 40 Alkyl groups of C 2 ~C 40 Alkenyl group, C 2 ~C 40 Alkynyl groups, C 3 ~C 40 Cycloalkyl groups having 3 to 40 ring atoms, heterocycloalkyl groups having 3 to 40 ring atoms, C 6 ~C 60 and heteroaryl groups having 5 to 60 ring atoms. In this case, when there are a plurality of the above-mentioned substituents, they may be the same or different.

[0026] Specifically, the substitution product represented by the above formula S1 may be a substitution product represented by any one of the following formulae S1-A to S1-D, but is not limited thereto. [ka] In the above formulas S1-A to S1-D, Y 1 , Y 3 , and Y 5 may be the same or different, and each independently represents N or C(R 1 ), where Y 1 , Y 3 , and Y 5 At least one of C(R 1 ) is multiple, multiple R 1 may be the same or different from each other, Y 2 and Y 5 may be the same or different, and each independently represents N or C(R 1 ), where Y 2 and Y 5 At least one of C(R 1 ) is multiple, multiple R 1 may be the same or different from each other, Y 1 and Y 3 may be the same or different, and each independently represents N or C(R 1 ), where Y 1 and Y 3 At least one of C(R 1 ) is multiple, multiple R 1 may be the same or different from each other, Y 1 and Y 5 may be the same or different, and each independently represents N or C(R 1 ), where Y 1 and Y 5At least one of C(R 1 ) is multiple, multiple R 1 may be the same or different from each other, Z 1 is O or S, R 1 is hydrogen, deuterium, halogen group, cyano group, nitro group, amino group, C 1 ~C 40 Alkyl groups of C 2 ~C 40 Alkenyl group, C 2 ~C 40 Alkynyl groups, C 3 ~C 40 Cycloalkyl groups having 3 to 40 ring atoms, heterocycloalkyl groups having 3 to 40 ring atoms, C 6 ~C 60 aryl groups, heteroaryl groups with 5 to 60 ring atoms, C 1 ~C 40 Alkyloxy groups, C 6 ~C 60 Aryloxy groups, C 1 ~C 40 Alkylsilyl group, C 6 ~C 60 Arylsilyl groups, C 1 ~C 40 Alkylboron group, C 6 ~C 60 Arylboron groups, C 6 ~C 60 Arylphosphine groups, C 6 ~C 60 and C 6 ~C 60 or an adjacent group (e.g., R 1 -R 1 ) to form a condensed ring, Above R 1The alkyl group, the alkenyl group, the alkynyl group, the cycloalkyl group, the heterocycloalkyl group, the aryl group, the heteroaryl group, the alkyloxy group, the aryloxy group, the alkylsilyl group, the arylsilyl group, the alkylboron group, the arylboron group, the arylphosphine group, the arylphosphine oxide group, the arylamine group, and the fused ring each independently represent a deuterium atom, a halogen atom, a cyano group, a nitro group, a C 2 ~C 40 Alkenyl group, C 2 ~C 40 Alkynyl groups, C 3 ~C 40 Cycloalkyl groups having 3 to 40 ring atoms, heterocycloalkyl groups having 3 to 40 ring atoms, C 1 ~C 40 Alkyl groups of C 6 ~C 60 aryl groups, heteroaryl groups with 5 to 60 ring atoms, C 1 ~C 40 Alkyloxy groups, C 6 ~C 60 Aryloxy groups, C 1 ~C 40 Alkylsilyl group, C 6 ~C 60 Arylsilyl groups, C 1 ~C 40 Alkylboron group, C 6 ~C 60 Arylboron groups, C 6 ~C 60 Arylphosphine groups, C 6 ~C 60 and C 6 ~C 60 and when there are a plurality of the above-mentioned substituents, they may be the same or different.

[0027] The compound represented by the above formula S2 may be a substituted compound represented by the following formula S2-A. [ka] In the above formula S2-A, Y 6 , Y 7 , and Y 9 may be the same or different, and each independently represents N, N(R 2 ), C(R 3 ) or C(R 4 )(R 5 ), where Y 6 , Y 7 , and Y 9 At least one of the following is N or N(R 2 ), where C(R 3 ) is multiple, multiple R 3 may be the same or different, in which case, C(R 4 )(R 5 ) is multiple, multiple R 4 may be the same or different from each other, and multiple R 5 may be the same or different from each other, R 2 ~R 5 , and R S may be the same or different, and each independently represents hydrogen, deuterium, a halogen group, a cyano group, a nitro group, an amino group, C 1 ~C 40 Alkyl groups of C 2 ~C 40 Alkenyl group, C 2 ~C 40 Alkynyl groups, C 3 ~C 40 Cycloalkyl groups having 3 to 40 ring atoms, heterocycloalkyl groups having 3 to 40 ring atoms, C 6 ~C 60 aryl groups, heteroaryl groups with 5 to 60 ring atoms, C 1 ~C 40 Alkyloxy groups, C 6 ~C 60 Aryloxy groups, C 1 ~C 40 Alkylsilyl group, C 6 ~C 60 Arylsilyl groups, C 1 ~C 40 Alkylboron group, C 6 ~C60 Arylboron groups, C 6 ~C 60 Arylphosphine groups, C 6 ~C 60 and C 6 ~C 60 or an adjacent group (e.g., R 2 -R 3 , R 4 -R 5 , R 2 -R 4 , R 3 -R 4 ) to form a condensed ring, Above R 2 ~R 5 , and R S The alkyl group, the alkenyl group, the alkynyl group, the cycloalkyl group, the heterocycloalkyl group, the aryl group, the heteroaryl group, the alkyloxy group, the aryloxy group, the alkylsilyl group, the arylsilyl group, the alkylboron group, the arylboron group, the arylphosphine group, the arylphosphine oxide group, the arylamine group, and the fused ring each independently represent a deuterium atom, a halogen atom, a cyano group, a nitro group, a C 2 ~C 40 Alkenyl group, C 2 ~C 40 Alkynyl groups, C 3 ~C 40 Cycloalkyl groups having 3 to 40 ring atoms, heterocycloalkyl groups having 3 to 40 ring atoms, C 1 ~C 40 Alkyl groups of C 6 ~C 60 aryl groups, heteroaryl groups with 5 to 60 ring atoms, C 1 ~C 40 Alkyloxy groups, C 6 ~C 60 Aryloxy groups, C 1 ~C 40 Alkylsilyl group, C 6 ~C 60 Arylsilyl groups, C 1 ~C 40 Alkylboron group, C 6 ~C 60Arylboron groups, C 6 ~C 60 Arylphosphine groups, C 6 ~C 60 and C 6 ~C 60 and when there are a plurality of the above-mentioned substituents, they may be the same or different.

[0028] In another embodiment, the Ar 1 may be a substituent selected from the group consisting of the following substituents S2-1 to S2-68, but is not limited thereto. [ka] [ka] [ka] [ka] In the above-mentioned substituents S2-1 to S2-68, * is a binding site to Chemical Formula 1 above, R 1 ~R 5 , and R S is as defined in the above formulas S1 to S10, k is an integer from 0 to 4, Me is a methyl group.

[0029] The above Ar 1 Therefore, the compound represented by Chemical Formula 1 above may be a compound represented by any one of Chemical Formulas 5 to 17 below, but is not limited thereto. [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] In the above Chemical Formula 5 to Chemical Formula 17, n is an integer from 0 to 3, L 1 is a direct bond, or C 6 ~C 60 and heteroarylene groups having 5 to 60 ring atoms, Y 1 , Y 3 , and Y 5 may be the same or different, and each independently represents N or C(R 1 ), where Y 1 , Y 3 , and Y 5 At least one of C(R 1 ) is multiple, multiple R 1may be the same or different from each other, Y 2 and Y 5 may be the same or different, and each independently represents N or C(R 1 ), where Y 2 and Y 5 At least one of C(R 1 ) is multiple, multiple R 1 may be the same or different from each other, Y 1 and Y 3 may be the same or different, and each independently represents N or C(R 1 ), where Y 1 and Y 3 At least one of C(R 1 ) is multiple, multiple R 1 may be the same or different from each other, Y 1 and Y 5 may be the same or different, and each independently represents N or C(R 1 ), where Y 1 and Y 5 At least one of C(R 1 ) is multiple, multiple R 1 may be the same or different from each other, Y 10 , Y 11 , and Z 1 are O or S, Y 6 , Y 7 , and Y 9 may be the same or different, and each independently represents N, N(R 2 ), C(R 3 ), or C(R 4 )(R 5 ), where Y 6 , Y 7 , and Y 9 At least one of the following is N or N(R2 ), where C(R 3 ) is multiple, multiple R 3 may be the same or different, in which case, C(R 4 )(R 5 ) is multiple, multiple R 4 may be the same or different, and multiple R 5 may be the same or different from each other, x and y are each 0 or 1; Ring Q is a benzene ring; a, d, and e are each an integer of 0 to 9; b and c are each an integer of 0 to 7, f, h, and i are each an integer of 0 to 4; g is an integer from 0 to 5; j is an integer from 0 to 3; k is an integer from 0 to 8; R 1 ~R 5 , and R S may be the same or different, and each independently represents hydrogen, deuterium, a halogen group, a cyano group, a nitro group, an amino group, C 1 ~C 40 Alkyl groups of C 2 ~C 40 Alkenyl group, C 2 ~C 40 Alkynyl groups, C 3 ~C 40 Cycloalkyl groups having 3 to 40 ring atoms, heterocycloalkyl groups having 3 to 40 ring atoms, C 6 ~C 60 aryl groups, heteroaryl groups with 5 to 60 ring atoms, C 1 ~C 40 Alkyloxy groups, C 6 ~C 60 Aryloxy groups, C 1 ~C 40 Alkylsilyl group, C 6 ~C 60 Arylsilyl groups, C 1 ~C 40 Alkylboron group, C 6 ~C60 Arylboron groups, C 6 ~C 60 Arylphosphine groups, C 6 ~C 60 and C 6 ~C 60 or which join adjacent groups to form a fused ring; Above R 1 ~R 5 , and R S The alkyl group, the alkenyl group, the alkynyl group, the cycloalkyl group, the heterocycloalkyl group, the aryl group, the heteroaryl group, the alkyloxy group, the aryloxy group, the alkylsilyl group, the arylsilyl group, the alkylboron group, the arylboron group, the arylphosphine group, the arylphosphine oxide group, the arylamine group, and the fused ring each independently represent a deuterium atom, a halogen atom, a cyano group, a nitro group, a C 2 ~C 40 Alkenyl group, C 2 ~C 40 Alkynyl groups, C 3 ~C 40 Cycloalkyl groups having 3 to 40 ring atoms, heterocycloalkyl groups having 3 to 40 ring atoms, C 1 ~C 40 Alkyl groups of C 6 ~C 60 aryl groups, heteroaryl groups with 5 to 60 ring atoms, C 1 ~C 40 Alkyloxy groups, C 6 ~C 60 Aryloxy groups, C 1 ~C 40 Alkylsilyl group, C 6 ~C 60 Arylsilyl groups, C 1 ~C 40 Alkylboron group, C 6 ~C 60 Arylboron groups, C 6 ~C 60 Arylphosphine groups, C 6 ~C 60 and C 6 ~C 60and when there are a plurality of the above-mentioned substituents, they may be the same or different.

[0030] The compound represented by Chemical Formula 1 according to the present invention as described above can be further embodied as the following A-1 to C126, but is not limited thereto. [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]

[0031] In the present invention, "alkyl" refers to a monovalent substituent derived from a linear or branched saturated hydrocarbon having 1 to 40 carbon atoms. Examples include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, hexyl, and the like.

[0032] In the present invention, "alkenyl" refers to a monovalent substituent derived from a linear or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and one or more carbon-carbon double bonds. Examples of this include, but are not limited to, vinyl, allyl, isopropenyl, 2-butenyl, etc.

[0033] In the present invention, "alkynyl" refers to a monovalent substituent derived from a linear or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and one or more carbon-carbon triple bonds. Examples of this include, but are not limited to, ethynyl, 2-propynyl, etc.

[0034] In the present invention, "cycloalkyl" refers to a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms. Examples thereof include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine, and the like.

[0035] In the present invention, "heterocycloalkyl" refers to a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 ring atoms, in which one or more carbons, preferably 1 to 3 carbons, in the ring are substituted with a heteroatom such as N, O, S, or Se. Examples include, but are not limited to, morpholine, piperazine, etc.

[0036] In the present invention, "aryl" means a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms, which is a single ring or a combination of two or more rings. The two or more rings may be in a pendant or condensed form. Examples of such groups include, but are not limited to, phenyl, naphthyl, phenanthryl, and anthryl.

[0037] In the present invention, "heteroaryl" means a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 60 nuclear atoms. In this case, one or more carbons in the ring, preferably 1 to 3 carbons, are substituted with heteroatoms such as N, O, S, or Se. In addition, two or more rings may be in a pendant or condensed form, and further in a condensed form with an aryl group. Examples of this include 6-membered monocyclic rings such as pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl, polycyclic rings such as phenoxathienyl, indolizinyl, indolyl, purinyl, quinolyl, benzothiazole, and carbazolyl, and 2-furanyl, N-imidazolyl, 2-isoxazolyl, 2-pyridinyl, and 2-pyrimidinyl, but are not limited thereto.

[0038] In the present invention, "alkyloxy" refers to a monovalent substituent represented by R'O-, where R' means an alkyl group having 1 to 40 carbon atoms, which may be linear, branched, or cyclic. Examples of alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, and pentoxy.

[0039] In the present invention, "aryloxy" refers to a monovalent substituent represented by RO-, where R means an aryl having 5 to 40 carbon atoms. Examples of this include, but are not limited to, phenyloxy, naphthyloxy, diphenyloxy, etc.

[0040] In the present invention, "alkylsilyl" refers to silyl substituted with an alkyl having 1 to 40 carbon atoms, including not only mono- but also di- and tri-alkylsilyl. Also, "arylsilyl" refers to silyl substituted with an aryl having 5 to 60 carbon atoms, including not only mono- but also polyarylsilyl such as di- and tri-arylsilyl.

[0041] In the present invention, the term "alkylboron group" refers to a boron group substituted with an alkyl group having 1 to 40 carbon atoms, and the term "arylboron group" refers to a boron group substituted with an aryl group having 6 to 60 carbon atoms.

[0042] In the present invention, the term "alkylphosphinyl group" refers to a phosphine group substituted with an alkyl group having 1 to 40 carbon atoms, and includes not only mono- but also di-alkylphosphinyl groups. In addition, in the present invention, the term "arylphosphinyl group" refers to a phosphine group substituted with a monoaryl or diaryl group having 6 to 60 carbon atoms, and includes not only mono- but also di-arylphosphinyl groups.

[0043] In the present invention, the term "arylamine" refers to an amine substituted with an aryl having 6 to 60 carbon atoms, and includes not only mono- but also di-arylamines.

[0044] In the present invention, the term "heteroarylamine" refers to an amine substituted with a heteroaryl having 5 to 60 ring atoms, and includes not only mono- but also di-heteroarylamines.

[0045] In the present invention, the (aryl)(heteroaryl)amine means an amine substituted with an aryl having 6 to 60 carbon atoms and a heteroaryl having 5 to 60 ring atoms.

[0046] In the present invention, the term "fused ring" refers to a fused aliphatic ring having 3 to 40 carbon atoms, a fused aromatic ring having 6 to 60 carbon atoms, a fused heteroaliphatic ring having 3 to 60 ring atoms, a fused heteroaromatic ring having 5 to 60 ring atoms, or a combination thereof.

[0047] <Organic electroluminescence element> The present invention also provides an organic electroluminescence device (hereinafter referred to as "organic EL device") containing the compound represented by Chemical Formula 1 above.

[0048] 1 to 4 show schematic diagrams of organic EL devices according to first to fourth embodiments of the present invention.

[0049] The organic EL devices according to the first to third embodiments of the present invention will be described in detail below with reference to FIGS.

[0050] 1 to 3, the organic EL device according to the present invention includes an anode 100, a cathode 200, and one or more organic layers 300 interposed between the anode and the cathode, at least one of which includes a compound represented by Chemical Formula 1. In this case, the compounds may be used alone or in combination of two or more.

[0051] The one or more organic layers 300 may include at least one of a hole injection layer 310, a hole transport layer 320, an emission layer 330, an electron transport auxiliary layer 360, an electron transport layer 340, and an electron injection layer 350, and at least one of the organic layers 300 includes a compound represented by Chemical Formula 1. Specifically, the organic layer including the compound represented by Chemical Formula 1 may be the electron transport layer 340. That is, the compound represented by Chemical Formula 1 is included in the organic EL device as an electron transport layer material. In such an organic EL device, electrons can be easily injected from the cathode or the electron injection layer to the electron transport layer due to the compound represented by Chemical Formula 1, and can be quickly moved from the electron transport layer to the emission layer, so that the binding strength between holes and electrons in the emission layer is high. Therefore, the organic EL device of the present invention has excellent luminous efficiency, power efficiency, brightness, etc. Furthermore, the compound represented by Chemical Formula 1 has excellent thermal stability and electrochemical stability, so that the performance of the organic EL device can be improved.

[0052] Such compounds of Formula 1 can be used alone or mixed with electron transport layer materials known in the art.

[0053] In the present invention, the electron transport layer material that can be mixed with the compound of Chemical Formula 1 may be an electron transport material known in the art. Examples of the electron transport material that can be used include oxazole-based compounds, isoxazole-based compounds, triazole-based compounds, isothiazole-based compounds, oxadiazole-based compounds, thiadiazole-based compounds, perylene-based compounds, aluminum complexes (e.g., Alq 3 , tris(8-quinolinolato)aluminum), gallium complexes (e.g., Gaq'2OPiv, Gaq'2OAc, 2(Gaq'2), etc., but are not limited thereto. These may be used alone or in combination of two or more.

[0054] In the present invention, when the compound of the above Chemical Formula 1 is used in combination with an electron transport layer material, the mixing ratio thereof is not particularly limited and can be appropriately adjusted within a range known in the art.

[0055] The structure of the organic EL element of the present invention described above is not particularly limited, but for example, an anode 100, one or more organic layers 300, and a cathode 200 are laminated in this order on a substrate (see Figs. 1 to 3). Furthermore, although not shown, an insulating layer or adhesive layer may be inserted at the interface between the electrode and the organic layer.

[0056] In one example, the organic EL device may have a structure in which an anode 100, a hole injection layer 310, a hole transport layer 320, an emitting layer 330, an electron transport layer 340, and a cathode 200 are stacked in this order on a substrate, as shown in Fig. 1. Optionally, an electron injection layer 350 may be located between the electron transport layer 340 and the cathode 200, as shown in Fig. 2. Also, an electron transport auxiliary layer 360 may be located between the emitting layer 330 and the electron transport layer 340 (see Fig. 3).

[0057] In the organic EL device of the present invention, except that at least one of the organic layers 300 (e.g., the electron transport layer 340) contains the compound represented by Chemical Formula 1, the organic layers and electrodes can be formed using materials and methods known in the art.

[0058] The organic layer can be formed by a vacuum deposition method or a solution coating method, such as, but not limited to, a spin coating method, a dip coating method, a doctor blade method, an inkjet printing method, or a thermal transfer method.

[0059] Substrates that can be used in the present invention are not particularly limited, and examples thereof include, but are not limited to, silicon wafers, quartz, glass plates, metal plates, plastic films, and sheets.

[0060] Examples of anode materials include metals such as vanadium, chromium, copper, zinc, and gold, and alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO:Al, or SnO 2Examples of suitable conductive materials include, but are not limited to: a combination of a metal such as Sb with an oxide; conductive polymers such as polythiopene, poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiopene] (PEDT), polypyrrole, or polyaniline; and carbon black.

[0061] Cathode materials include, for example, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver (Ag), tin, or lead, or alloys thereof; and LiF / Al or LiO 2 Examples of the material include, but are not limited to, multi-layered materials such as SiO2 / Al.

[0062] The hole injection layer, the hole transport layer, the light emitting layer, and the electron injection layer are not particularly limited, and materials well known in the art can be used.

[0063] An organic EL device according to a fourth embodiment of the present invention will now be described with reference to FIG.

[0064] 4, the organic EL device according to the fourth embodiment of the present invention is a tandem type device, and includes, on a substrate, an anode 100 and a cathode 200 facing each other, a plurality of light-emitting units 400, 500 interposed between the anode 100 and the cathode 200, and a charge generation layer 600 interposed between adjacent light-emitting units 400, 500 and including an N-type charge generation layer 610 and a P-type charge generation layer 620. The N-type charge generation layer 610 includes the compound represented by Chemical Formula 1 above.

[0065] Such a tandem type organic EL element has at least two light emitting units, and the number of light emitting units can be increased by interposing a charge generating layer between adjacent light emitting units.

[0066] In one example, the plurality of light-emitting units may include a first light-emitting unit 400, a second light-emitting unit 500, ..., and an m-1 light-emitting unit (m is an integer of 3 or more, specifically 3 to 4). In this case, a charge generating layer 600 including an N-type charge generating layer 610 and a P-type charge generating layer 620 is disposed between adjacent light-emitting units, and the N-type charge generating layer 610 includes a compound represented by Chemical Formula 1 above.

[0067] Specifically, the organic EL device according to the present invention comprises an anode 100 and a cathode 200 facing each other: a first light-emitting unit 400 disposed on the anode 100; a second light-emitting unit 500 disposed on the first light-emitting unit 400; and a charge generating layer 600 interposed between the first and second light-emitting units 400, 500 and including an N-type charge generating layer 610 and a P-type charge generating layer 620. In this case, the N-type charge generating layer 610 contains the compound represented by Chemical Formula 1 above.

[0068] Each light-emitting unit 400, 500 includes a hole transport layer 410, 510, an emissive layer 420, 520, and an electron transport layer 430, 530. Specifically, the first light-emitting unit 400 includes a first hole transport layer 410, a first emissive layer 420, and a first electron transport layer 430, and the second light-emitting unit 500 includes a hole transport layer 510, an emissive layer 520, and an electron transport layer 530. Optionally, the first light-emitting unit 400 may further include a hole injection layer 440.

[0069] The hole transport layers 410 and 510, the light emitting layers 420 and 520, the electron transport layers 430 and 530, and the hole injection layer 440 are not particularly limited, and materials known in the art can be used.

[0070] The charge generation layer (CGL) 600 is disposed between the adjacent light emitting units 400 and 500 to adjust the charge between the light emitting units 400 and 500 and maintain the charge balance.

[0071] The charge generation layer 600 includes an N-type charge generation layer 610 positioned adjacent to the first light-emitting unit 400 to supply electrons to the first light-emitting unit 400, and a P-type charge generation layer 620 positioned adjacent to the second light-emitting unit 500 to supply holes to the second light-emitting unit 500.

[0072] The N-type charge generation layer 610 includes the compound represented by Chemical Formula 1. The compound represented by Chemical Formula 1 has excellent electron mobility and therefore has excellent electron injection and transport capabilities. Therefore, when the compound represented by Chemical Formula 1 is used as an N-type charge generation layer material in an organic EL device, an increase in the progressive driving voltage and a decrease in the life span of the device can be prevented.

[0073] In one example, the N-type charge generating layer 610 includes a host having electron transport properties, and the host is a compound represented by Formula 1 above.

[0074] The N-type charge generation layer 610 may further include an N-type dopant.

[0075] The N-type dopant that can be used in the present invention is not particularly limited as long as it is generally used as an N-type charge generating layer in the technical field, and examples thereof include alkali metals such as Li, Na, K, Rb, Cs, and Fr; alkaline earth metals such as Be, Mg, Ca, Sr, Ba, and Ra; lanthanoid metals such as La (lanthanum), Ce (cerium), Pr (preseodyminum), Nd (neodymium), Pm (promethium), Sm (samarium), Eu (europium), Gd (gadolinium), Tb (terbium), Dy (dysprosium), Ho (holmium), Er (erbium), Tm (thulium), Yb (yetterbium), and Lu (lutetium); and compounds of one or more of the above metals. Also, the dopant may be an organic N-type dopant that has electron donor properties and can donate at least a portion of an electronic charge to an organic host (e.g., a compound of Chemical Formula 1) to form a charge transfer complex with the organic host, and examples of such an organic dopant include bis(ethylenedithio)tetrathiafulvalene (BEDT-TTF), tetrathiafulvalene (TTF), etc.

[0076] The thickness of the N-type charge generating layer 610 is not particularly limited, and may be, for example, in the range of about 5 to 30 nm.

[0077] The P-type charge generating layer 620 may be made of a metal or a P-type doped organic material. Here, examples of the metal include Al, Cu, Fe, Pb, Zn, Au, Pt, W, In, Mo, Ni, and Ti, which may be used alone or in an alloy of two or more. The P-type dopant and host material used in the P-type doped organic material are not particularly limited as long as they are commonly used. For example, the P-type dopant may be F. 4 -TCNQ (2,3,5,6-tetrafluoro-7,7,8,8-tetracyano-quinodimethane), iodine, FeCl 3 , FeF 3 , and SbCl 5These may be used alone or in combination of two or more. Examples of the host include, but are not limited to, NPB (N,N'-bis(naphthalene-1-yl)-N,N'-bis(phenyl)-benzidine), TPD (N,N'-bis(3-methylphenyl)N,N'-bis(phenyl)-benzidine), and TNB (N,N,N',N'-tetra-naphthaleneyl-benzidine). These may be used alone or in combination of two or more.

[0078] The substrate (not shown), anode 100, cathode 200, hole injection layer, hole transport layer, light emitting layer, and electron injection layer are the same as those described in the first to third embodiments above, and therefore their description will be omitted. EXAMPLES

[0079] The present invention will be described in detail below with reference to examples. However, the examples described below are merely illustrative of the present invention, and the present invention is not limited to these examples.

[0080] [Synthesis Example 1] Synthesis of Compound A-1 [ka] 6-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)phenanthridine (7 g, 18.3 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (4.9 g, 18.3 mmol), Pd(PPh 3 ) 4 (1.1 g, 0.9 mmol), and K 2 CO 3 (7.6 g, 54.9 mmol) in 50 ml of toluene, 10 ml of EtOH, 2 The mixture was poured into 10 ml of HO and heated under reflux for 12 hours. After the reaction was completed, the organic layer was extracted with methylene chloride and diluted with MgSO 4 The solvent in the filtered organic layer was removed, and the target compound (7.8 g, yield 87%) was obtained using column chromatography. [LCMS]:488

[0081] [Synthesis Example 2] Synthesis of Compound A-3 [ka] The target compound (8.6 g, yield 83%) was obtained in the same manner as in [Synthesis Example 1], except that 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 1. [LCMS]:564

[0082] [Synthesis Example 3] Synthesis of Compound A-7 [ka] The target compound (7.7 g, yield 86%) was obtained in the same manner as in [Synthesis Example 1], except that 4-chloro-2,6-diphenylpyrimidine was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 1. [LCMS]:487

[0083] [Synthesis Example 4] Synthesis of Compound A-8 [ka] The target compound (8.6 g, yield 83%) was obtained in the same manner as in [Synthesis Example 1], except that 4-(4-bromophenyl)-2,6-diphenylpyrimidine was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 1. [LCMS]:563

[0084] [Synthesis Example 5] Synthesis of Compound A-13 [ka] The target compound (8.5 g, yield 82%) was obtained in the same manner as in [Synthesis Example 1], except that 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 1. [LCMS]:564

[0085] [Synthesis Example 6] Synthesis of Compound A-19 [ka] The target compound (8.6 g, yield 83%) was obtained in the same manner as in [Synthesis Example 1], except that 4-([1,1'-biphenyl]-4-yl)-6-chloro-2-phenylpyrimidine was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 1. [LCMS]:563

[0086] [Synthesis Example 7] Synthesis of Compound A-25 [ka] The target compound (8.5 g, yield 82%) was obtained in the same manner as in [Synthesis Example 1], except that 4-chloro-2-phenyl-6-(4-(pyridin-3-yl)phenyl)pyrimidine was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 1. [LCMS]:564

[0087] [Synthesis Example 8] Synthesis of Compound A-31 [ka] The target compound (8.3 g, yield 80%) was obtained in the same manner as in [Synthesis Example 1], except that 2-chloro-4-phenyl-6-(4-(pyridin-3-yl)phenyl)-1,3,5-triazine was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 1. [LCMS]:565

[0088] [Synthesis Example 9] Synthesis of Compound A-37 [ka] The target compound (8.0 g, yield 77%) was obtained in the same manner as in [Synthesis Example 1], except that 2-(5-bromopyridin-2-yl)-4,6-diphenyl-1,3,5-triazine was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 1. [LCMS]:565

[0089] [Synthesis Example 10] Synthesis of Compound A-38 [ka] The target compound (8.0 g, yield 77%) was obtained in the same manner as in [Synthesis Example 1], except that 2-(4-bromopyridin-2-yl)-4,6-diphenyl-1,3,5-triazine was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 1. [LCMS]:565

[0090] [Synthesis Example 11] Synthesis of Compound A-40 [ka] The target compound (7.9 g, yield 76%) was obtained in the same manner as in [Synthesis Example 1], except that 4-(4-bromopyridin-2-yl)-2,6-diphenylpyrimidine was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 1. [LCMS]:564

[0091] [Synthesis Example 12] Synthesis of Compound A-43 [ka] The target compound (9.0 g, yield 76%) was obtained in the same manner as in [Synthesis Example 1], except that 4-([1,1'-biphenyl]-4-yl)-6-(5-bromopyridin-2-yl)-2-phenylpyrimidine was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 1. [LCMS]:640

[0092] [Synthesis Example 13] Synthesis of Compound A-49 [ka] The target compound (7.6 g, yield 80%) was obtained in the same manner as in [Synthesis Example 1], except that 4-chloro-2-phenylbenzo[4,5]thieno[3,2-d]pyrimidine was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 1. [LCMS]:517

[0093] [Synthesis Example 14] Synthesis of Compound A-51 [ka] The target compound (8.6 g, yield 79%) was obtained in the same manner as in [Synthesis Example 1], except that 4-(3-bromophenyl)-2-phenylbenzo[4,5]thieno[3,2-d]pyrimidine was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 1. [LCMS]:593

[0094] [Synthesis Example 15] Synthesis of Compound A-52 [ka] The target compound (7.5 g, yield 82%) was obtained in the same manner as in [Synthesis Example 1], except that 4-chloro-2-phenylbenzofuro[3,2-d]pyrimidine was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 1. [LCMS]:501

[0095] [Synthesis Example 16] Synthesis of Compound A-55 [ka] The target compound (7.8 g, yield 82%) was obtained in the same manner as in [Synthesis Example 1], except that 2-chloro-4-phenylbenzo[4,5]thieno[3,2-d]pyrimidine was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 1. [LCMS]:517

[0096] [Synthesis Example 17] Synthesis of Compound A-56 [ka] The target compound (8.6 g, yield 79%) was obtained in the same manner as in [Synthesis Example 1], except that 2-(4-bromophenyl)-4-phenylbenzo[4,5]thieno[3,2-d]pyrimidine was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 1. [LCMS]:593

[0097] [Synthesis Example 18] Synthesis of Compound A-61 [ka] The target compound (7.6 g, yield 79%) was obtained in the same manner as in [Synthesis Example 1], except that 2-bromo-6,8-diphenyl-[1,2,4]triazolo[1,5-a]pyridine was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 1. [LCMS]:526

[0098] [Synthesis Example 19] Synthesis of Compound A-70 [ka] The target compound (8.0 g, yield 77%) was obtained in the same manner as in [Synthesis Example 1], except that 2-chloro-3,5,6-triphenylpyrazine was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 1. [LCMS]:563

[0099] [Synthesis Example 20] Synthesis of Compound A-72 [ka] The target compound (9.2 g, yield 78%) was obtained in the same manner as in [Synthesis Example 1], except that 2-(3-bromophenyl)-3,5,6-triphenylpyrazine was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 1. [LCMS]:639

[0100] [Synthesis Example 21] Synthesis of Compound A-73 [ka] The target compound (6.7 g, yield 79%) was obtained in the same manner as in [Synthesis Example 1], except that 2-chloro-4-phenylquinazoline was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 1. [LCMS]:461

[0101] [Synthesis Example 22] Synthesis of Compound A-75 [ka] The target compound (7.0 g, yield 78%) was obtained in the same manner as in [Synthesis Example 1], except that 4'-chloro-3,2':6',3''-terpyridine was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 1. [LCMS]:488

[0102] [Synthesis Example 23] Synthesis of Compound A-79 [ka] The target compound (6.3 g, yield 81%) was obtained in the same manner as in [Synthesis Example 1], except that 4-bromodibenzo[b,d]furan was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 1. [LCMS]:423

[0103] [Synthesis Example 24] Synthesis of Compound A-81 [ka] The target compound (6.3 g, yield 81%) was obtained in the same manner as in [Synthesis Example 1], except that 3-bromodibenzo[b,d]furan was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 1. [LCMS]:423

[0104] [Synthesis Example 25] Synthesis of Compound A-82 [ka] The target compound (6.7 g, yield 77%) was obtained in the same manner as in [Synthesis Example 1], except that 9-bromonaphtho[2,1-b]benzofuran was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 1. [LCMS]:473

[0105] [Synthesis Example 26] Synthesis of Compound A-88 [ka] The target compound (6.9 g, yield 77%) was obtained in the same manner as in [Synthesis Example 1], except that 8-bromobenzo[b]naphtho[1,2-d]thiophene was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 1. [LCMS]:489

[0106] [Synthesis Example 27] Synthesis of Compound A-89 [ka] The target compound (6.4 g, yield 80%) was obtained in the same manner as in [Synthesis Example 1], except that 3-bromodibenzo[b,d]thiophene was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 1. [LCMS]:439

[0107] [Synthesis Example 28] Synthesis of Compound A-96 [ka] The target compound (6.7 g, yield 80%) was obtained in the same manner as in [Synthesis Example 1], except that 2-(4-bromophenyl)naphthalene was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 1. [LCMS]:459

[0108] [Synthesis Example 29] Synthesis of Compound A-97 [ka] The target compound (6.6 g, yield 78%) was obtained in the same manner as in [Synthesis Example 1], except that 1-bromo-4-phenylnaphthalene was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 1. [LCMS]:459

[0109] [Synthesis Example 30] Synthesis of Compound A-100 [ka] The target compound (6.9 g, yield 74%) was obtained in the same manner as in [Synthesis Example 1], except that 9-bromo-10-phenylanthracene was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 1. [LCMS]:509

[0110] [Synthesis Example 31] Synthesis of Compound A-104 [ka] The target compound (9.3 g, yield 74%) was obtained in the same manner as in [Synthesis Example 1], except that 2-bromo-9,10-di(naphthalen-2-yl)anthracene was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 1. [LCMS]:685

[0111] [Synthesis Example 32] Synthesis of Compound A-106 [ka] The target compound (6.8 g, yield 76%) was obtained in the same manner as in [Synthesis Example 1], except that 5'-bromo-1,1':3',1''-terphenyl was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 1. [LCMS]:485

[0112] [Synthesis Example 33] Synthesis of Compound A-110 [ka] The target compound (6.0 g, yield 76%) was obtained in the same manner as in [Synthesis Example 1], except that 9-bromophenanthrene was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 1. [LCMS]:433

[0113] [Synthesis Example 34] Synthesis of Compound A-112 [ka] The target compound (7.0 g, yield 75%) was obtained in the same manner as in [Synthesis Example 1], except that 9-(3-bromophenyl)phenanthrene was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 1. [LCMS]:509

[0114] [Synthesis Example 35] Synthesis of Compound A-113 [ka] The target compound (6.0 g, yield 76%) was obtained in the same manner as in [Synthesis Example 1], except that 2-bromophenanthrene was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 1. [LCMS]:433

[0115] [Synthesis Example 36] Synthesis of Compound A-116 [ka] The target compound (6.3 g, yield 71%) was obtained in the same manner as in [Synthesis Example 1], except that 2-bromotriphenylene was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 1. [LCMS]:483

[0116] [Synthesis Example 37] Synthesis of Compound A-119 [ka] The target compound (6.1 g, yield 73%) was obtained in the same manner as in [Synthesis Example 1], except that 2-bromopyrene was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 1. [LCMS]:457

[0117] [Synthesis Example 38] Synthesis of Compound A-121 [ka] The target compound (6.1 g, yield 73%) was obtained in the same manner as in [Synthesis Example 1], except that 1-bromopyrene was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 1. [LCMS]:457

[0118] [Synthesis Example 39] Synthesis of Compound A-122 [ka] The target compound (6.1 g, yield 72%) was obtained in the same manner as in [Synthesis Example 1], except that 4-bromo-2,9-dimethyl-1,10-phenanthroline was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 1. [LCMS]:463

[0119] [Synthesis Example 40] Synthesis of Compound B-1 [ka] 6-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)phenanthridine (7 g, 18.3 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (4.9 g, 18.3 mmol), Pd(PPh 3 ) 4 (1.1 g, 0.9 mmol), and K 2 CO 3 (7.6 g, 54.9 mmol) in 50 ml of toluene, 10 ml of EtOH, 2 The mixture was poured into 10 ml of HO and heated under reflux for 12 hours. After the reaction was completed, the organic layer was extracted with methylene chloride and diluted with MgSO 4 The solvent in the filtered organic layer was removed, and the target compound (7.7 g, yield 86%) was obtained using column chromatography. [LCMS]:488

[0120] [Synthesis Example 41] Synthesis of Compound B-3 [ka] The target compound (8.5 g, yield 82%) was obtained in the same manner as in [Synthesis Example 40], except that 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 40. [LCMS]:564

[0121] [Synthesis Example 42] Synthesis of Compound B-7 [ka] The target compound (7.6 g, yield 85%) was obtained in the same manner as in [Synthesis Example 40], except that 4-chloro-2,6-diphenylpyrimidine was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 40. [LCMS]:487

[0122] [Synthesis Example 43] Synthesis of Compound B-8 [ka] The target compound (8.5 g, yield 82%) was obtained in the same manner as in [Synthesis Example 40], except that 4-(4-bromophenyl)-2,6-diphenylpyrimidine was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 40. [LCMS]:563

[0123] [Synthesis Example 44] Synthesis of Compound B-13 [ka] The target compound (8.4 g, yield 81%) was obtained in the same manner as in [Synthesis Example 40], except that 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 40. [LCMS]:564

[0124] [Synthesis Example 45] Synthesis of Compound B-19 [ka] The target compound (8.5 g, yield 82%) was obtained in the same manner as in [Synthesis Example 40], except that 4-([1,1'-biphenyl]-4-yl)-6-chloro-2-phenylpyrimidine was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 40. [LCMS]:563

[0125] [Synthesis Example 46] Synthesis of Compound B-25 [ka] The target compound (8.4 g, yield 81%) was obtained in the same manner as in [Synthesis Example 40], except that 4-chloro-2-phenyl-6-(4-(pyridin-3-yl)phenyl)pyrimidine was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 40. [LCMS]:564

[0126] [Synthesis Example 47] Synthesis of Compound B-31 [ka] The target compound (8.2 g, yield 79%) was obtained in the same manner as in [Synthesis Example 40], except that 2-chloro-4-phenyl-6-(4-(pyridin-3-yl)phenyl)-1,3,5-triazine was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 40. [LCMS]:565

[0127] [Synthesis Example 48] Synthesis of Compound B-37 [ka] The target compound (7.9 g, yield 76%) was obtained in the same manner as in [Synthesis Example 40], except that 2-(5-bromopyridin-2-yl)-4,6-diphenyl-1,3,5-triazine was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 40. [LCMS]:565

[0128] [Synthesis Example 49] Synthesis of Compound B-38 [ka] The target compound (7.9 g, yield 76%) was obtained in the same manner as in [Synthesis Example 40], except that 2-(4-bromopyridin-2-yl)-4,6-diphenyl-1,3,5-triazine was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 40. [LCMS]:565

[0129] [Synthesis Example 50] Synthesis of Compound B-40 [ka] The target compound (7.8 g, yield 75%) was obtained in the same manner as in [Synthesis Example 40], except that 4-(4-bromopyridin-2-yl)-2,6-diphenylpyrimidine was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 40. [LCMS]:564

[0130] [Synthesis Example 51] Synthesis of Compound B-43 [ka] The target compound (8.9 g, yield 75%) was obtained in the same manner as in [Synthesis Example 40], except that 4-([1,1'-biphenyl]-4-yl)-6-(5-bromopyridin-2-yl)-2-phenylpyrimidine was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 40. [LCMS]:640

[0131] [Synthesis Example 52] Synthesis of Compound B-49 [ka] The target compound (7.5 g, yield 79%) was obtained in the same manner as in [Synthesis Example 40], except that 4-chloro-2-phenylbenzo[4,5]thieno[3,2-d]pyrimidine was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 40. [LCMS]:517

[0132] [Synthesis Example 53] Synthesis of Compound B-51 [ka] The target compound (8.5 g, yield 78%) was obtained in the same manner as in [Synthesis Example 40], except that 4-(3-bromophenyl)-2-phenylbenzo[4,5]thieno[3,2-d]pyrimidine was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 40. [LCMS]:593

[0133] [Synthesis Example 54] Synthesis of Compound B-52 [ka] The target compound (7.4 g, yield 81%) was obtained in the same manner as in Synthesis Example 40, except that 4-chloro-2-phenylbenzofuro[3,2-d]pyrimidine was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 40. [LCMS]:501

[0134] [Synthesis Example 55] Synthesis of Compound B-55 [ka] The target compound (7.7 g, yield 81%) was obtained in the same manner as in [Synthesis Example 40], except that 2-chloro-4-phenylbenzo[4,5]thieno[3,2-d]pyrimidine was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 40. [LCMS]:517

[0135] [Synthesis Example 56] Synthesis of Compound B-56 [ka] The target compound (8.5 g, yield 78%) was obtained in the same manner as in [Synthesis Example 40], except that 2-(4-bromophenyl)-4-phenylbenzo[4,5]thieno[3,2-d]pyrimidine was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 40. [LCMS]:593

[0136] [Synthesis Example 57] Synthesis of Compound B-61 [ka] The target compound (7.5 g, yield 78%) was obtained in the same manner as in [Synthesis Example 40], except that 2-bromo-6,8-diphenyl-[1,2,4]triazolo[1,5-a]pyridine was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 40. [LCMS]:526

[0137] [Synthesis Example 58] Synthesis of Compound B-70 [ka] The target compound (7.9 g, yield 76%) was obtained in the same manner as in Synthesis Example 40, except that 2-chloro-3,5,6-triphenylpyrazine was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 40. [LCMS]:563

[0138] [Synthesis Example 59] Synthesis of Compound B-72 [ka] The target compound (9.1 g, yield 77%) was obtained in the same manner as in Synthesis Example 40, except that 2-(3-bromophenyl)-3,5,6-triphenylpyrazine was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 40. [LCMS]:639

[0139] [Synthesis Example 60] Synthesis of Compound B-73 [ka] The target compound (6.6 g, yield 78%) was obtained in the same manner as in Synthesis Example 40, except that 2-chloro-4-phenylquinazoline was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 40. [LCMS]:461

[0140] [Synthesis Example 61] Synthesis of Compound B-75 [ka] The target compound (6.9 g, yield 77%) was obtained in the same manner as in [Synthesis Example 40], except that 4'-chloro-3,2':6',3''-terpyridine was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 40. [LCMS]:488

[0141] [Synthesis Example 62] Synthesis of Compound B-79 [ka] The target compound (6.2 g, yield 80%) was obtained in the same manner as in [Synthesis Example 40], except that 4-bromodibenzo[b,d]furan was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 40. [LCMS]:423

[0142] [Synthesis Example 63] Synthesis of Compound B-81 [ka] The target compound (6.2 g, yield 80%) was obtained in the same manner as in [Synthesis Example 40], except that 3-bromodibenzo[b,d]furan was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 40. [LCMS]:423

[0143] [Synthesis Example 64] Synthesis of Compound B-82 [ka] The target compound (6.6 g, yield 76%) was obtained in the same manner as in [Synthesis Example 40], except that 9-bromonaphtho[2,1-b]benzofuran was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 40. [LCMS]:473

[0144] [Synthesis Example 65] Synthesis of Compound B-88 [ka] The target compound (6.8 g, yield 76%) was obtained in the same manner as in [Synthesis Example 40], except that 8-bromobenzo[b]naphtho[1,2-d]thiophene was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 40. [LCMS]:489

[0145] [Synthesis Example 66] Synthesis of Compound B-89 [ka] The target compound (6.3 g, yield 79%) was obtained in the same manner as in [Synthesis Example 40], except that 3-bromodibenzo[b,d]thiophene was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 40. [LCMS]:439

[0146] [Synthesis Example 67] Synthesis of Compound B-96 [ka] The target compound (6.6 g, yield 79%) was obtained in the same manner as in [Synthesis Example 40], except that 2-(4-bromophenyl)naphthalene was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 40. [LCMS]:459

[0147] [Synthesis Example 68] Synthesis of Compound B-97 [ka] The target compound (6.5 g, yield 77%) was obtained in the same manner as in [Synthesis Example 40], except that 1-bromo-4-phenylnaphthalene was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 40. [LCMS]:459

[0148] [Synthesis Example 69] Synthesis of Compound B-100 [ka] The target compound (6.8 g, yield 73%) was obtained in the same manner as in [Synthesis Example 40], except that 9-bromo-10-phenylanthracene was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 40. [LCMS]:509

[0149] [Synthesis Example 70] Synthesis of Compound B-104 [ka] The target compound (9.2 g, yield 73%) was obtained in the same manner as in [Synthesis Example 40], except that 2-bromo-9,10-di(naphthalen-2-yl)anthracene was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 40. [LCMS]:685

[0150] [Synthesis Example 71] Synthesis of Compound B-106 [ka] The target compound (6.7 g, yield 75%) was obtained in the same manner as in [Synthesis Example 40], except that 5'-bromo-1,1':3',1''-terphenyl was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 40. [LCMS]:485

[0151] [Synthesis Example 72] Synthesis of Compound B-110 [ka] The target compound (5.9 g, yield 75%) was obtained in the same manner as in [Synthesis Example 40], except that 9-bromophenanthrene was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 40. [LCMS]:433

[0152] [Synthesis Example 73] Synthesis of Compound B-112 [ka] The target compound (6.9 g, yield 74%) was obtained in the same manner as in [Synthesis Example 40], except that 9-(3-bromophenyl)phenanthrene was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 40. [LCMS]:509

[0153] [Synthesis Example 74] Synthesis of Compound B-113 [ka] The target compound (5.9 g, yield 75%) was obtained in the same manner as in [Synthesis Example 40], except that 2-bromophenanthrene was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 40. [LCMS]:433

[0154] [Synthesis Example 75] Synthesis of Compound B-116 [ka] The target compound (6.2 g, yield 70%) was obtained in the same manner as in [Synthesis Example 40], except that 2-bromotriphenylene was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 40. [LCMS]:483

[0155] [Synthesis Example 76] Synthesis of Compound B-119 [ka] The target compound (6.0 g, yield 72%) was obtained in the same manner as in Synthesis Example 40, except that 2-bromopyrene was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 40. [LCMS]:457

[0156] [Synthesis Example 77] Synthesis of Compound B-121 [ka] The target compound (6.0 g, yield 72%) was obtained in the same manner as in [Synthesis Example 40], except that 1-bromopyrene was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 40. [LCMS]:457

[0157] [Synthesis Example 78] Synthesis of Compound B-122 [ka] The target compound (6.0 g, yield 71%) was obtained in the same manner as in [Synthesis Example 40], except that 4-bromo-2,9-dimethyl-1,10-phenanthroline was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 40. [LCMS]:463

[0158] [Synthesis Example 79] Synthesis of Compound C-1 [ka] 6-(6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)phenanthridine (7 g, 18.3 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (4.9 g, 18.3 mmol), Pd(PPh 3 ) 4 (1.1 g, 0.9 mmol), and K 2 CO 3 (7.6 g, 54.9 mmol) in 50 ml of toluene, 10 ml of EtOH, 2 The mixture was poured into 10 ml of HO and heated under reflux for 12 hours. After the reaction was completed, the organic layer was extracted with methylene chloride and diluted with MgSO 4 The solvent in the filtered organic layer was removed, and the target compound (7.5 g, yield 84%) was obtained using column chromatography. [LCMS]488

[0159] [Synthesis Example 80] Synthesis of Compound C-3 [ka] The target compound (8.7 g, yield 84%) was obtained in the same manner as in Synthesis Example 79, except that 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 79. [LCMS]:564

[0160] [Synthesis Example 81] Synthesis of Compound C-7 [ka] The target compound (7.5 g, yield 84%) was obtained in the same manner as in Synthesis Example 79, except that 4-chloro-2,6-diphenylpyrimidine was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 79. [LCMS]:487

[0161] [Synthesis Example 82] Synthesis of Compound C-8 [ka] The target compound (8.7 g, yield 84%) was obtained in the same manner as in Synthesis Example 79, except that 4-(4-bromophenyl)-2,6-diphenylpyrimidine was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 79. [LCMS]:563

[0162] [Synthesis Example 83] Synthesis of Compound C-13 [ka] The target compound (8.3 g, yield 80%) was obtained in the same manner as in Synthesis Example 79, except that 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 79. [LCMS]:564

[0163] [Synthesis Example 84] Synthesis of Compound C-19 [ka] The target compound (8.7 g, yield 84%) was obtained in the same manner as in [Synthesis Example 79], except that 4-([1,1'-biphenyl]-4-yl)-6-chloro-2-phenylpyrimidine was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 79. [LCMS]:563

[0164] [Synthesis Example 85] Synthesis of Compound C-25 [ka] The target compound (8.3 g, yield 80%) was obtained in the same manner as in Synthesis Example 79, except that 4-chloro-2-phenyl-6-(4-(pyridin-3-yl)phenyl)pyrimidine was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 79. [LCMS]:564

[0165] [Synthesis Example 86] Synthesis of Compound C-31 [ka] The target compound (8.3 g, yield 80%) was obtained in the same manner as in Synthesis Example 79, except that 2-chloro-4-phenyl-6-(4-(pyridin-3-yl)phenyl)-1,3,5-triazine was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 79. [LCMS]:565

[0166] [Synthesis Example 87] Synthesis of Compound C-37 [ka] The target compound (7.8 g, yield 71%) was obtained in the same manner as in [Synthesis Example 79], except that 2-(5-bromopyridin-2-yl)-4,6-diphenyl-1,3,5-triazine was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 40. [LCMS]:565

[0167] [Synthesis Example 88] Synthesis of Compound C-38 [ka] The target compound (8.1 g, yield 78%) was obtained in the same manner as in Synthesis Example 79, except that 2-(4-bromopyridin-2-yl)-4,6-diphenyl-1,3,5-triazine was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 79. [LCMS]:565

[0168] [Synthesis Example 89] Synthesis of Compound C-40 [ka] The target compound (8.0 g, yield 77%) was obtained in the same manner as in Synthesis Example 79, except that 4-(4-bromopyridin-2-yl)-2,6-diphenylpyrimidine was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 79. [LCMS]:564

[0169] [Synthesis Example 90] Synthesis of Compound C-43 [ka] The target compound (8.8 g, yield 75%) was obtained in the same manner as in [Synthesis Example 79], except that 4-([1,1'-biphenyl]-4-yl)-6-(5-bromopyridin-2-yl)-2-phenylpyrimidine was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 79. [LCMS]:640

[0170] [Synthesis Example 91] Synthesis of Compound C-49 [ka] The target compound (7.4 g, yield 78%) was obtained in the same manner as in [Synthesis Example 79], except that 4-chloro-2-phenylbenzo[4,5]thieno[3,2-d]pyrimidine was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 79. [LCMS]:517

[0171] [Synthesis Example 92] Synthesis of Compound C-51 [ka] The target compound (8.7 g, yield 80%) was obtained in the same manner as in Synthesis Example 79, except that 4-(3-bromophenyl)-2-phenylbenzo[4,5]thieno[3,2-d]pyrimidine was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 79. [LCMS]:593

[0172] [Synthesis Example 93] Synthesis of Compound C-52 [ka] The target compound (7.3 g, yield 80%) was obtained in the same manner as in Synthesis Example 79, except that 4-chloro-2-phenylbenzofuro[3,2-d]pyrimidine was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 79. [LCMS]:501

[0173] [Synthesis Example 94] Synthesis of Compound C-55 [ka] The target compound (7.8 g, yield 82%) was obtained in the same manner as in [Synthesis Example 79], except that 2-chloro-4-phenylbenzo[4,5]thieno[3,2-d]pyrimidine was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 79. [LCMS]:517

[0174] [Synthesis Example 95] Synthesis of Compound C-56 [ka] The target compound (8.6 g, yield 79%) was obtained in the same manner as in Synthesis Example 79, except that 2-(4-bromophenyl)-4-phenylbenzo[4,5]thieno[3,2-d]pyrimidine was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 79. [LCMS]:593

[0175] [Synthesis Example 96] Synthesis of Compound C-61 [ka] The target compound (7.7 g, yield 80%) was obtained in the same manner as in Synthesis Example 79, except that 2-bromo-6,8-diphenyl-[1,2,4]triazolo[1,5-a]pyridine was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 79. [LCMS]:526

[0176] [Synthesis Example 97] Synthesis of Compound C-70 [ka] The target compound (8.0 g, yield 77%) was obtained in the same manner as in Synthesis Example 79, except that 2-chloro-3,5,6-triphenylpyrazine was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 79. [LCMS]:563

[0177] [Synthesis Example 98] Synthesis of Compound C-72 [ka] The target compound (9.0 g, yield 77%) was obtained in the same manner as in Synthesis Example 79, except that 2-(3-bromophenyl)-3,5,6-triphenylpyrazine was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 79. [LCMS]:639

[0178] [Synthesis Example 99] Synthesis of Compound C-73 [ka] The target compound (6.5 g, yield 77%) was obtained in the same manner as in Synthesis Example 79, except that 2-chloro-4-phenylquinazoline was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 79. [LCMS]:461

[0179] [Synthesis Example 100] Synthesis of Compound C-75 [ka] The target compound (7.0 g, yield 78%) was obtained in the same manner as in Synthesis Example 79, except that 4'-chloro-3,2':6',3''-terpyridine was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 79. [LCMS]:488

[0180] [Synthesis Example 101] Synthesis of Compound C-79 [ka] The target compound (6.4 g, yield 82%) was obtained in the same manner as in [Synthesis Example 79], except that 4-bromodibenzo[b,d]furan was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 79. [LCMS]:423

[0181] [Synthesis Example 102] Synthesis of Compound C-81 [ka] The target compound (6.3 g, yield 81%) was obtained in the same manner as in Synthesis Example 79, except that 3-bromodibenzo[b,d]furan was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 79. [LCMS]:423

[0182] [Synthesis Example 103] Synthesis of Compound C-82 [ka] The target compound (6.5 g, yield 75%) was obtained in the same manner as in Synthesis Example 79, except that 9-bromonaphtho[2,1-b]benzofuran was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 79. [LCMS]:473

[0183] [Synthesis Example 104] Synthesis of Compound C-88 [ka] The target compound (6.7 g, yield 75%) was obtained in the same manner as in Synthesis Example 79, except that 8-bromobenzo[b]naphtho[1,2-d]thiophene was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 79. [LCMS]:489

[0184] [Synthesis Example 105] Synthesis of Compound C-89 [ka] The target compound (6.4 g, yield 80%) was obtained in the same manner as in [Synthesis Example 79], except that 3-bromodibenzo[b,d]thiophene was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 79. [LCMS]:439

[0185] [Synthesis Example 106] Synthesis of Compound C-96 [ka] The target compound (6.8 g, yield 81%) was obtained in the same manner as in Synthesis Example 79, except that 2-(4-bromophenyl)naphthalene was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 79. [LCMS]:459

[0186] [Synthesis Example 107] Synthesis of Compound C-97 [ka] The target compound (6.7 g, yield 79%) was obtained in the same manner as in Synthesis Example 79, except that 1-bromo-4-phenylnaphthalene was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 79. [LCMS]:459

[0187] [Synthesis Example 108] Synthesis of Compound C-100 [ka] The target compound (6.9 g, yield 74%) was obtained in the same manner as in Synthesis Example 79, except that 9-bromo-10-phenylanthracene was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 79. [LCMS]:509

[0188] [Synthesis Example 109] Synthesis of Compound C-104 [ka] The target compound (9.3 g, yield 74%) was obtained in the same manner as in Synthesis Example 79, except that 2-bromo-9,10-di(naphthalen-2-yl)anthracene was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 79. [LCMS]:685

[0189] [Synthesis Example 110] Synthesis of Compound C-106 [ka] The target compound (6.6 g, yield 74%) was obtained in the same manner as in Synthesis Example 79, except that 5'-bromo-1,1':3',1''-terphenyl was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 79. [LCMS]:485

[0190] [Synthesis Example 111] Synthesis of Compound C-110 [ka] The target compound (6.1 g, yield 77%) was obtained in the same manner as in Synthesis Example 79, except that 9-bromophenanthrene was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 79. [LCMS]:433

[0191] [Synthesis Example 112] Synthesis of Compound C-112 [ka] The target compound (7.1 g, yield 76%) was obtained in the same manner as in Synthesis Example 79, except that 9-(3-bromophenyl)phenanthrene was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 79. [LCMS]:509

[0192] [Synthesis Example 113] Synthesis of Compound C-113 [ka] The target compound (6.0 g, yield 76%) was obtained in the same manner as in Synthesis Example 79, except that 2-bromophenanthrene was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 79. [LCMS]:433

[0193] [Synthesis Example 114] Synthesis of Compound C-116 [ka] The target compound (6.4 g, yield 72%) was obtained in the same manner as in Synthesis Example 79, except that 2-bromotriphenylene was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 79. [LCMS]:483

[0194] [Synthesis Example 115] Synthesis of Compound C-119 [ka] The target compound (6.1 g, yield 73%) was obtained in the same manner as in Synthesis Example 79, except that 2-bromopyrene was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 79. [LCMS]:457

[0195] [Synthesis Example 116] Synthesis of Compound C-121 [ka] The target compound (6.2 g, yield 74%) was obtained in the same manner as in Synthesis Example 79, except that 1-bromopyrene was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 79. [LCMS]:457

[0196] [Synthesis Example 117] Synthesis of Compound C-122 [ka] The target compound (6.1 g, yield 72%) was obtained in the same manner as in Synthesis Example 79, except that 4-bromo-2,9-dimethyl-1,10-phenanthroline was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine used in Synthesis Example 79. [LCMS]:463

[0197] [Examples 1 to 10] Preparation of blue organic EL elements Compound A-1 synthesized in Synthesis Example was purified to high purity by sublimation using a known ordinary method, and then a blue organic EL device was fabricated as follows.

[0198] First, a glass substrate coated with a thin film of ITO (Indium Tin Oxide) with a thickness of 1200 Å was ultrasonically cleaned with distilled water. After cleaning with distilled water, ultrasonic cleaning was performed with solvents such as isopropyl alcohol, acetone, and methanol, and the substrate was then dried and transferred to a UV ozone cleaner (Power sonic 405, manufactured by Fashintech Co., Ltd.) where it was cleaned with UV for 5 minutes and then transferred to a vacuum deposition machine.

[0199] On the ITO transparent electrode prepared as above, compound 1 and compound 2 were co-deposited in a weight ratio of 98:2 to form a hole injection layer having a thickness of 100 Å, compound 1 was then deposited on the hole injection layer to form a hole transport layer having a thickness of 1400 Å, compound 3 was then deposited on the hole transport layer to a thickness of 50 Å to form a hole transport auxiliary layer, and compound 4 and compound 5 were co-deposited in a weight ratio of 98:2 to form a light emitting layer having a thickness of 200 Å. Compound 6 was deposited on the light emitting layer to form an electron transport auxiliary layer having a thickness of 50 Å, compound A-1 and compound 7 were then co-deposited in a weight ratio of 1:1 to form an electron transport layer having a thickness of 300 Å, LiF was deposited on the electron transport layer to form an electron injection layer having a thickness of 10 Å, and Al was then deposited on the electron injection layer to form a cathode having a thickness of 1000 Å to manufacture an organic light emitting device.

[0200] The structures of the compounds 1 to 7 used here are as follows: [ka]

[0201] [Examples 2 to 117] Preparation of blue organic EL devices Blue organic EL devices were produced in the same manner as in Example 1, except that the compounds shown in Table 1 below were used instead of Compound A-1 used as the electron transport layer material.

[0202] [Comparative Examples 1 to 12] Preparation of blue organic EL elements A blue organic EL device was produced in the same manner as in Example 1, except that the following compounds A to L were used instead of compound A-1 used as the electron transport layer material. [ka] [ka] [ka]

[0203] [Evaluation example 1] For the blue organic EL devices fabricated in Examples 1 to 117 and Comparative Examples 1 to 12, a current density of 10 mA / cm 2 The driving voltage, current efficiency, and emission wavelength were measured at 1000 Hz, and the results are shown in Table 1 below.

[0204] [Table 1] JPEG2025510071000171.jpg249170JPEG2025510071000172.jpg252170JPEG2025510071000173.jpg115170

[0205] As shown in Table 1 above, the blue organic EL devices of Examples 1 to 117 in which the compounds of the present invention were used in the electron transport layer were found to be superior in terms of driving voltage, emission peak, current efficiency, and device life compared to the organic EL devices of Comparative Examples 1 to 4 in which the penanthroline was linked directly or via a linker, the organic EL devices of Comparative Examples 5 to 11 in which no pyridine was bonded to the penanthridine, and the organic EL device of Comparative Example 12 in which three pyridines were bonded to the penanthridine.

[0206] [Example 118] Preparation of organic EL element Compound A-1 synthesized in Synthesis Example was purified to high purity by sublimation using a known ordinary method, and then a blue organic EL device was fabricated as follows.

[0207] First, a glass substrate coated with a thin film of ITO (Indium Tin Oxide) with a thickness of 1500 Å was ultrasonically cleaned with distilled water. After cleaning with distilled water, ultrasonic cleaning was performed with solvents such as isopropyl alcohol, acetone, and methanol, and the substrate was then dried and transferred to a UV ozone cleaner (Power sonic 405, manufactured by Fashintech Co., Ltd.) where it was cleaned with UV for 5 minutes and then transferred to a vacuum deposition machine.

[0208] On the ITO transparent electrode prepared as above, compound 1 and compound 2 were co-deposited in a weight ratio of 98:2 to form a hole injection layer having a thickness of 100 Å, then compound 1 was deposited on the hole injection layer to form a hole transport layer having a thickness of 200 Å, then compound 3 was deposited on the hole transport layer to a thickness of 50 Å to form a hole transport auxiliary layer, and compound 4 and compound 5 were co-deposited in a weight ratio of 98:2 to form a light emitting layer having a thickness of 200 Å. Compound 7 was deposited on the light emitting layer to a thickness of 150 Å to form an electron transport region, and compound A-1 of the embodiment was deposited on the electron transport region to a thickness of 80 Å to form a charge generating layer. Compound 1 and compound 2 were co-deposited on the charge generation layer in a weight ratio of 98:2 to form a hole injection layer having a thickness of 100 Å, compound 1 was then deposited on the hole injection layer to form a hole transport layer having a thickness of 350 Å, compound 3 was deposited on the hole transport layer in a thickness of 50 Å to form a hole transport auxiliary layer, and compound 4 and compound 5 were co-deposited in a weight ratio of 98:2 to form a light emitting layer having a thickness of 200 Å. Compound 6 was deposited on the light emitting layer to form an electron transport auxiliary layer having a thickness of 50 Å, compound 7 and compound 8 were then deposited in a weight ratio of 1:1 to form an electron transport region having a thickness of 300 Å, LiF was deposited on the electron transport layer to form an electron injection layer having a thickness of 10 Å, and Al was then deposited on the electron injection layer to form a cathode having a thickness of 1000 Å to manufacture an organic light emitting device.

[0209] The structures of compounds 1 to 7 used here are as described in Example 1, and the structure of compound 8 is as follows: [ka]

[0210] [Examples 119 to 234] Preparation of organic EL elements Organic EL devices were produced in the same manner as in Example 118, except that the compounds shown in Table 2 were used instead of Compound A-1 used in Example 118 as the charge generating layer material.

[0211] [Comparative Examples 13 to 24] Preparation of organic EL elements Organic EL devices were produced in the same manner as in Example 118, except that compounds A to L were used instead of compound A-1 used as the charge generating layer material. Compounds A to L used at this time are as described in Comparative Examples 1 to 12.

[0212] [Evaluation example 2] For the organic EL devices fabricated in Examples 118 to 234 and Comparative Examples 13 to 24, a current density of 10 mA / cm 2 The driving voltage, current efficiency, and emission wavelength were measured at 1000 Hz, and the results are shown in Table 2 below.

[0213] [Table 2] JPEG2025510071000176.jpg244170JPEG2025510071000177.jpg245170JPEG2025510071000178.jpg127170

[0214] As shown in Table 2 above, the organic EL elements of Examples 118 to 234, in which the compounds of the present invention were used in the charge generating layer, were found to be superior in terms of driving voltage, current efficiency, and lifespan to the organic EL elements of Comparative Examples 13 to 16 in which the penanthroline was linked directly or via a linker, the organic EL elements of Comparative Examples 17 to 23 in which no pyridine was bonded to the penanthridine, and the organic EL element of Comparative Example 24 in which three pyridines were bonded to the penanthridine.

Claims

1. A compound represented by the following chemical formula 1. 【Chemistry 1】 (In the formula, n is an integer from 0 to 3, L １ is a direct bond, or C ６ ~C ６０ and heteroarylene groups having 5 to 60 ring atoms, Ar １ is hydrogen, deuterium (D), halogen group, cyano group, nitro group, amino group, C １ ~C ４０ Alkyl groups of C ２ ~C ４０ an alkenyl group of C ２ ~C ４０ an alkynyl group of C ３ ~C ４０ a cycloalkyl group having 3 to 40 ring atoms; a heterocycloalkyl group having 3 to 40 ring atoms; ６ ~C ６０ an aryl group having 5 to 60 ring atoms; １ ~C ４０ an alkyloxy group of C ６ ~C ６０ an aryloxy group of C １ ~C ４０ an alkylsilyl group of C ６ ~C ６０ an arylsilyl group of C １ ~C ４０ an alkylboron group of C ６ ~C ６０ Arylboron groups of C ６ ~C ６０ an arylphosphine group of C ６ ~C ６０ an arylphosphine oxide group of C ６ ~C ６０ and C ２ ~C ４０ C substituted with an alkenyl group ６ ~C ６０ or which join adjacent groups to form a fused ring; The above L １ Arylene groups and heteroarylene groups of the above formula Ar １ The alkyl group, the alkenyl group, the alkynyl group, the cycloalkyl group, the heterocycloalkyl group, the aryl group, the heteroaryl group, the alkyloxy group, the aryloxy group, the alkylsilyl group, the arylsilyl group, the alkylboron group, the arylboron group, the arylphosphine group, the arylphosphine oxide group, the arylamine group, the aryl group substituted with the alkenyl group, and the fused ring each independently represent a deuterium atom, a halogen atom, a cyano group, a nitro group, a C ２ ~C ４０ an alkenyl group of C ２ ~C ４０ an alkynyl group of C ３ ~C ４０ a cycloalkyl group having 3 to 40 ring atoms; a heterocycloalkyl group having 3 to 40 ring atoms; １ ~C ４０ Alkyl groups of C ６ ~C ６０ an aryl group having 5 to 60 ring atoms; １ ~C ４０ an alkyloxy group of C ６ ~C ６０ an aryloxy group of C １ ~C ４０ an alkylsilyl group of C ６ ~C ６０ an arylsilyl group of C １ ~C ４０ an alkylboron group of C ６ ~C ６０ Arylboron groups of C ６ ~C ６０ an arylphosphine group of C ６ ~C ６０ and an arylphosphine oxide group of C ６ ~C ６０ The arylamine groups may be substituted or unsubstituted with one or more substituents selected from the group consisting of the following:

2. The compound according to claim 1, wherein the compound represented by the above formula 1 is represented by any one of the following formulas 2 to 4: 【Chemistry 2】 【Chemistry 3】 【Chemistry 4】 (In the formula, n, L １ , and Ar １ is as defined in claim 1. 【Request 3】 【Chemistry 5】 is a linker group represented by any one of the following chemical formulas L1 to L5. 【Chemistry 6】 【Chemistry 7】 【Chemistry 8】 【Chemistry 9】 【Chemistry 10】 (In the formula, n1 and n2 each represent an integer from 0 to 3, provided that 0≦n1+n2≦3; l is an integer from 0 to 4; m is an integer from 0 to 3; Multiple R ａ may be the same or different from each other, R ａ is hydrogen, deuterium, halogen group, cyano group, nitro group, amino group, C １ ~C ４０ Alkyl groups of C ２ ~C ４０ an alkenyl group of C ２ ~C ４０ an alkynyl group of C ３ ~C ４０ a cycloalkyl group having 3 to 40 ring atoms; a heterocycloalkyl group having 3 to 40 ring atoms; ６ ~C ６０ an aryl group having 5 to 60 ring atoms; １ ~C ４０ an alkyloxy group of C ６ ~C ６０ an aryloxy group of C １ ~C ４０ an alkylsilyl group of C ６ ~C ６０ an arylsilyl group of C １ ~C ４０ an alkylboron group of C ６ ~C ６０ Arylboron groups of C ６ ~C ６０ an arylphosphine group of C ６ ~C ６０ and an arylphosphine oxide group of C ６ ~C ６０ The arylamine groups are selected from the group consisting of

4. The above Ar １ is a substituted compound represented by any one selected from the group consisting of the following formulas S1 to S12: 【Chemistry 11】 (In the formula, Y １ ~Y ５ may be the same or different, and each independently represents N or C(R １ ), where Y １ ~Y ５ At least one of C(R １ When there are a plurality of R １ may be the same or different from each other, Y ６ ~Y ９ may be the same or different, and each independently represents N, N(R ２ ), C(R ３ ) or C(R ４ ) (R ５ ), where Y ６ ~Y ９ At least one of the groups is N or N(R ２ ), where C(R ３ When there are a plurality of R ３ may be the same or different, in which case C(R ４ ) (R ５ When there are a plurality of R ４ may be the same or different, and multiple R ５ may be the same or different from each other, Y １０ and Y １１ are each O or S, Ring Q is a benzene ring; x and y are each 0 or 1; a, d, and e are each an integer from 0 to 9; b and c each represent an integer from 0 to 7; f, h, and i each represent an integer from 0 to 4; g is an integer from 0 to 5; j is an integer from 0 to 3; k is an integer from 0 to 8; R １ ~R ５ , and R Ｓ may be the same or different, and each independently represents hydrogen, deuterium, a halogen group, a cyano group, a nitro group, an amino group, C １ ~C ４０ Alkyl groups of C ２ ~C ４０ an alkenyl group of C ２ ~C ４０ an alkynyl group of C ３ ~C ４０ a cycloalkyl group having 3 to 40 ring atoms; ６ ~C ６０ an aryl group having 5 to 60 ring atoms; １ ~C ４０ an alkyloxy group of C ６ ~C ６０ an aryloxy group of C １ ~C ４０ an alkylsilyl group of C ６ ~C ６０ an arylsilyl group of C １ ~C ４０ an alkylboron group of C ６ ~C ６０ Arylboron groups of C ６ ~C ６０ an arylphosphine group of C ６ ~C ６０ and an arylphosphine oxide group of C ６ ~C ６０ or which join adjacent groups to form a fused ring; The above R １ ~R ５ , and R Ｓ The alkyl group, the alkenyl group, the alkynyl group, the cycloalkyl group, the heterocycloalkyl group, the aryl group, the heteroaryl group, the alkyloxy group, the aryloxy group, the alkylsilyl group, the arylsilyl group, the alkylboron group, the arylboron group, the arylphosphine group, the arylphosphine oxide group, the arylamine group, and the fused ring each independently represent deuterium, halogen, cyano group, nitro group, C ２ ~C ４０ an alkenyl group of C ２ ~C ４０ an alkynyl group of C ３ ~C ４０ a cycloalkyl group having 3 to 40 ring atoms; a heterocycloalkyl group having 3 to 40 ring atoms; １ ~C ４０ Alkyl groups of C ６ ~C ６０ an aryl group having 5 to 60 ring atoms; １ ~C ４０ an alkyloxy group of C ６ ~C ６０ an aryloxy group of C １ ~C ４０ an alkylsilyl group of C ６ ~C ６０ an arylsilyl group of C １ ~C ４０ an alkylboron group of C ６ ~C ６０ Arylboron groups of C ６ ~C ６０ an arylphosphine group of C ６ ~C ６０ and an arylphosphine oxide group of C ６ ~C ６０ The arylamine groups may be substituted or unsubstituted with one or more substituents selected from the group consisting of the following:

5. The above Ar １ is a substituent selected from the group consisting of the following substituents S2-1 to S2-68. 【Chemistry 12】 【Chemistry 13】 【Chemistry 14】 【Chemistry 15】 (In the above substituents S2-1 to S2-68, R １ ~R ５ , and R Ｓ is as defined in claim 4, k is an integer from 0 to 4.

6. The compound according to claim 1, wherein the compound represented by Chemical Formula 1 is represented by any one of Chemical Formulas 5 to 17 below. 【Chemistry 16】 【Chemistry 17】 【Chemistry 18】 【Chemistry 19】 【Chemistry 20】 【Chemistry 21】 【Chemical 22】 【Chemistry 23】 【Chemistry 24】 【Chemistry 25】 【Chemistry 26】 【Chemistry 27】 【Chemistry 28】 (In the formula, n is an integer from 0 to 3, L １ is a direct bond, or C ６ ~C ６０ and heteroarylene groups having 5 to 60 ring atoms, Y １ , Y ３ , and Y ５ may be the same or different, and each independently represents N or C(R １ ), where Y １ , Y ３ , and Y ５ At least one of C(R １ When there are a plurality of R １ may be the same or different from each other, Y ２ and Y ５ may be the same or different, and each independently represents N or C(R １ ), where Y ２ and Y ５ At least one of C(R １ When there are a plurality of R １ may be the same or different from each other, Y １ and Y ３ may be the same or different, and each independently represents N or C(R １ ), where Y １ and Y ３ At least one of C(R １ When there are a plurality of R １ may be the same or different from each other, Y １ and Y ５ may be the same or different, and each independently represents N or C(R １ ), where Y １ and Y ５ At least one of C(R １ When there are a plurality of R １ may be the same or different from each other, Y １０ , Y １１ , and Z １ are each O or S, Y ６ , Y ７ , and Y ９ may be the same or different, and each independently represents N, N(R ２ ), C(R ３ ), or C(R ４ ) (R ５ ), where Y ６ , Y ７ , and Y ９ At least one of the groups is N or N(R ２ ), where C(R ３ When there are a plurality of R ３ may be the same or different, in which case C(R ４ ) (R ５ When there are a plurality of R ４ may be the same or different, and multiple R ５ may be the same or different from each other, x and y are each 0 or 1; Ring Q is a benzene ring; a, d, and e are each an integer from 0 to 9; b and c each represent an integer from 0 to 7; f, h, and i each represent an integer from 0 to 4; g is an integer from 0 to 5; j is an integer from 0 to 3; k is an integer from 0 to 8; R １ ~R ５ , and R Ｓ may be the same or different, and each independently represents hydrogen, deuterium, a halogen group, a cyano group, a nitro group, an amino group, C １ ~C ４０ Alkyl groups of C ２ ~C ４０ an alkenyl group of C ２ ~C ４０ an alkynyl group of C ３ ~C ４０ a cycloalkyl group having 3 to 40 ring atoms; ６ ~C ６０ an aryl group having 5 to 60 ring atoms; １ ~C ４０ an alkyloxy group of C ６ ~C ６０ an aryloxy group of C １ ~C ４０ an alkylsilyl group of C ６ ~C ６０ an arylsilyl group of C １ ~C ４０ an alkylboron group of C ６ ~C ６０ Arylboron groups of C ６ ~C ６０ an arylphosphine group of C ６ ~C ６０ and an arylphosphine oxide group of C ６ ~C ６０ or which join adjacent groups to form a fused ring; The above R １ ~R ５ , and R Ｓ The alkyl group, the alkenyl group, the alkynyl group, the cycloalkyl group, the heterocycloalkyl group, the aryl group, the heteroaryl group, the alkyloxy group, the aryloxy group, the alkylsilyl group, the arylsilyl group, the alkylboron group, the arylboron group, the arylphosphine group, the arylphosphine oxide group, the arylamine group, and the fused ring each independently represent deuterium, halogen, cyano group, nitro group, C ２ ~C ４０ an alkenyl group of C ２ ~C ４０ an alkynyl group of C ３ ~C ４０ a cycloalkyl group having 3 to 40 ring atoms; a heterocycloalkyl group having 3 to 40 ring atoms; １ ~C ４０ Alkyl groups of C ６ ~C ６０ an aryl group having 5 to 60 ring atoms; １ ~C ４０ an alkyloxy group of C ６ ~C ６０ an aryloxy group of C １ ~C ４０ an alkylsilyl group of C ６ ~C ６０ an arylsilyl group of C １ ~C ４０ an alkylboron group of C ６ ~C ６０ Arylboron groups of C ６ ~C ６０ an arylphosphine group of C ６ ~C ６０ and an arylphosphine oxide group of C ６ ~C ６０ The arylamine groups may be substituted or unsubstituted with one or more substituents selected from the group consisting of the following:

7. The compound according to claim 1, wherein the compound represented by the above chemical formula 1 is selected from the group consisting of A-1 to C-126 below. 【Chemical Formula 29】 【Chemistry 30】 【Chemistry 31】 【Chemistry 32】 【Chemical 33】 【Chemical 34】 【Chemistry 35】 【Chemical Formula 36】 【Chemical 37】 【Chemical Formula 38】 【Chemical Formula 39】 【Chemistry 40】

8. An anode, a cathode, and one or more organic layers interposed between the anode and the cathode; 8. An organic electroluminescence device, wherein at least one of the one or more organic layers comprises the organic compound according to claim 1.

9. The organic electroluminescence device according to claim 8 , wherein the organic layer containing the organic compound is an electron transport layer.

10. an anode and a cathode disposed in spaced relation to one another; a plurality of light-emitting units interposed between the anode and the cathode; and a charge generating layer interposed between adjacent light emitting units, the charge generating layer including an N-type charge generating layer and a P-type charge generating layer; Including, Each of the light-emitting units includes a hole transport layer, a light-emitting layer, and an electron transport layer; 8. An organic EL element, wherein the N-type charge generating layer comprises the organic compound according to claim 1.

11. The N-type charge generating layer comprises a host having electron transport properties; 11. The organic electroluminescence device according to claim 10, wherein the one host is an organic compound according to any one of claims 1 to 7.

12. The organic electroluminescence device according to claim 11 , wherein the N-type charge generating layer further comprises an N-type dopant.

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