Organic compounds and organic electroluminescent elements 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.

Claims

1. The compound represented by the following chemical formula 1. 【Chemistry 1】 (In the formula, n is an integer between 0 and 3. L １ This is a direct bond, or C ６ ~C ６０ Selected from the group consisting of arylene groups and heteroarylene groups with 5 to 60 nuclear atoms, Ar １ is a substituent represented by the following formulas S1, S2, and S4 to S11, deuterium (D), nitro group, amino group, C １ to C ４０ alkyl group, C ２ to C ４０ alkenyl group, C ２ to C ４０ alkynyl group, C ３ to C ４０ cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C １ to C ４０ alkyloxy group, C ６ to C ６０ aryloxy group, C １ to C ４０ alkylsilyl group, C ６ to C ６０ arylsilyl group, C １ to C ４０ alkylboron group, C ６ to C ６０ arylboron group, C ６ to C ６０ arylphosphine group, C ６ to C ６０ arylphosphine oxide group, C ６ to C ６０ arylamine group, and C ２ to C ４０ aryl group substituted with an alkenyl group of C ６ to C ６０ selected from the group consisting of, or combined with adjacent groups to form a condensed ring, 【Chemistry 2】 Y １ ~Y ５ These may be the same or different from each other, and each may independently be N or C(R) １ ) and, however, Y １ ~Y ５ At least one of them is N, and in this case C(R １ If there are multiple R １ They may be the same or different from each other. Y ６ ~Y ９ These may be the same or different from each other, and each may independently be N, N(R) ２ ), C (R ３ ) or C (R ４ ) (Caution ５ ) and, however, Y ６ ~Y ９ At least one of the following is N or N(R) ２ ) and at this time C(R ３ If there are multiple R ３ These may be the same or different from each other, in which case C(R ４ ) (Caution ５ If there are multiple R ４ These may be the same or different from each other, and there may be multiple R ５ They may be the same or different from each other. Y １０ and Y １１ These are either O or S, Ring Q is a benzene ring, d and e are integers from 0 to 9, b and c are integers from 0 to 7, f, h, and i are integers from 0 to 4, g is an integer between 0 and 5. j is an integer between 0 and 3. R1 to R5 may be the same or different from each other, and each may independently be hydrogen, deuterium, halogen group, cyano group, nitro group, amino group, C1 to C40 alkyl group, C2 to C40 alkenyl group, C2 to C40 alkynyl group, C3 to C40 cycloalkyl group, heterocycloalkyl group with 3 to 40 nuclei, C6 to C60 aryl group, heteroaryl group with 5 to 60 nuclei, C1 to C40 alkyloxy group, C6 to C60 aryloxy group, C1 to C40 alkylsilyl group, C6 to C60 arylsilyl group, C1 to C40 alkylboron group, C6 to C60 arylboron group, C6 to C60 arylphosphine group, C6 to C60 Selected from the group consisting of an arylphosphine oxide group and an arylamine group from C6 to C60, or bonded to an adjacent group to form a condensed ring. R S are hydrogen, deuterium, halogen group, cyano group, nitro group, amino group, C １ ~C ４０ alkyl group, C ２ ~C ４０ The alkenyl group, C ２ ~C ４０ The alkynyl group, C ３ ~C ４０ Cycloalkyl groups, heterocycloalkyl groups with 3 to 40 nuclear atoms, C ６ ~C ６０ aryl group, heteroaryl group with 5 to 60 nuclear atoms, C １ ~C ４０ The alkyloxy group, C ６ ~C ６０ The aryloxy group, C １ ~C ４０ alkylsilyl group, C ６ ~C ６０ The arylsilyl group, C １ ~C ４０ alkylboron group, C ６ ~C ６０ The arylboron group, C ６ ~C ６０ The arylphosphine group, C ６ ~C ６０ The arylphosphine oxide group and C ６ ~C ６０ Selected from the group consisting of arylamine groups, The above R １ to R ５ , and R Ｓ 's 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, and arylamine group may each independently be substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium, halogen, cyano group, nitro group, C ２ to C ４０ 's alkenyl group, C ２ to C ４０ 's alkynyl group, C ３ to C ４０ 's cycloalkyl group, a heterocycloalkyl group having 3 to 40 ring atoms, C １ to C ４０ 's alkyl group, C ６ to C ６０ 's aryl group, a heteroaryl group having 5 to 60 ring atoms, C １ to C ４０ 's alkyloxy group, C ６ to C ６０ 's aryloxy group, C １ to C ４０ 's alkylsilyl group, C ６ to C ６０ 's arylsilyl group, C １ to C ４０ 's alkylboron group, C ６ to C ６０ 's arylboron group, C ６ to C ６０ 's arylphosphine group, C ６ to C ６０ 's arylphosphine oxide group, and C ６ to C ６０ 's arylamine group, and may be substituted or unsubstituted. When there are a plurality of the above substituents, they may be the same as or different from each other. The above L １ Arylene groups and heteroarylene groups, and the above Ar １ The alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl 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 condensed ring are each independently composed of deuterium, cyano group, nitro group, and C ２ ~C ４０ The alkenyl group, C ２ ~C ４０ The alkynyl group, C ３ ~C ４０ Cycloalkyl groups, heterocycloalkyl groups with 3 to 40 nuclear atoms, C １ ~C ４０ alkyl group, C ６ ~C ６０ aryl group, heteroaryl group with 5 to 60 nuclear atoms, C １ ~C ４０ The alkyloxy group, C ６ ~C ６０ The aryloxy group, C １ ~C ４０ alkylsilyl group, C ６ ~C ６０ The arylsilyl group, C １ ~C ４０ alkylboron group, C ６ ~C ６０ The arylboron group, C ６ ~C ６０ The arylphosphine group, C ６ ~C ６０ The arylphosphine oxide group and C ６ ~C ６０ The substituents may be substituted or unsubstituted with one or more substituents selected from the group consisting of arylamine groups, and if there are multiple substituents, they may be identical or different from one another.

2. The compound according to claim 1, wherein the compound represented by the above chemical formula 1 is represented by any one of the following chemical formulas 2 to 4. 【Transformation 3】 【Chemistry 4】 【Transformation 5】 (In the formula, n, L １ , and Ar １ (This is as defined in claim 1.) 【Request Item 3】 【Chemistry 6】 The compound according to claim 1, wherein is a linker group represented by any one of the following chemical formulas L1 to L5. 【Transformation 7】 【Transformation 8】 【Chemistry 9】 【Chemistry 10】 【Chemistry 11】 (In the formula, n1 and n2 are integers between 0 and 3, where 0 ≤ n1 + n2 ≤ 3. l is an integer between 0 and 4. m is an integer between 0 and 3. Multiple R ａ They may be the same or different from each other. R ａ These are hydrogen, deuterium, halogen groups, cyano groups, nitro groups, amino groups, and C １ ~C ４０ alkyl group, C ２ ~C ４０ The alkenyl group, C ２ ~C ４０ The alkynyl group, C ３ ~C ４０ Cycloalkyl groups, heterocycloalkyl groups with 3 to 40 nuclear atoms, C ６ ~C ６０ aryl group, heteroaryl group with 5 to 60 nuclear atoms, C １ ~C ４０ The alkyloxy group, C ６ ~C ６０ The aryloxy group, C １ ~C ４０ alkylsilyl group, C ６ ~C ６０ The arylsilyl group, C １ ~C ４０ alkylboron group, C ６ ~C ６０ The arylboron group, C ６ ~C ６０ The arylphosphine group, C ６ ~C ６０ The arylphosphine oxide group and C ６ ~C ６０ (Selected from the group consisting of arylamine groups.)

4. The above Ar １ The compound according to claim 1, wherein the substituent is selected from the group consisting of the substituents S2-1 to S2-39, S2-47 to S2-56, S2-65, and S2-66. 【Chemistry 12】 【Chemistry 13】 【Chemistry 14】 【Chemistry 15】 (In the substituents S2-1 to S2-39, S2-47 to S2-56, S2-65, and S2-66 above, R １ ~R ５ , and R Ｓ This is as defined in claim 1, Z1 is either O or S, k is an integer between 0 and 4.

5. The compound according to claim 1, wherein the compound represented by the above chemical formula 1 is represented by any one of the following chemical formulas 5 to 9 and 11 to 16. 【Chemistry 16】 【Chemistry 17】 [Chemistry 18] 【Chemistry 19】 【Chemistry 20】 【Chemistry 21】 【Chemistry 22】 【Chemistry 23】 【Chemistry 24】 【Chemistry 25】 【Chemistry 26】 (In the formula, n is an integer between 0 and 3. L １ This is a direct bond, or C ６ ~C ６０ Selected from the group consisting of arylene groups and heteroarylene groups with 5 to 60 nuclear atoms, Y １ , Y ３ , and Y ５ These may be the same or different from each other, and each may independently be N or C(R) １ ) and, however, Y １ , Y ３ , and Y ５ At least one of them is N, and in this case C(R １ If there are multiple R １ They may be the same or different from each other. Y ２ and Y ５ These may be the same or different from each other, and each may independently be N or C(R) １ ) and, however, Y ２ and Y ５ At least one of them is N, and in this case C(R １ If there are multiple R １ They may be the same or different from each other. Y １ and Y ３ These may be the same or different from each other, and each may independently be N or C(R) １ ) and, however, Y １ and Y ３ At least one of them is N, and in this case C(R １ If there are multiple R １ They may be the same or different from each other. Y １ and Y ５ These may be the same or different from each other, and each may independently be N or C(R) １ ) and, however, Y １ and Y ５ At least one of them is N, and in this case C(R １ If there are multiple R １ They may be the same or different from each other. Y １０ , Y １１ , and Z １ These are either O or S, Y ６ , Y ７ , and Y ９ These may be the same or different from each other, and each may independently be N, N(R) ２ ), C (R ３ ), or C (R ４ ) (Caution ５ ) and, however, Y ６ , Y ７ , and Y ９ At least one of the following is N or N(R) ２ ) and at this time C(R ３ If there are multiple R ３ These may be the same or different from each other, in which case C(R ４ ) (Caution ５ If there are multiple R ４ These may be the same or different from each other, and there may be multiple R ５ They may be the same or different from each other. Ring Q is a benzene ring, d and e are integers from 0 to 9, b and c are integers from 0 to 7, f, h, and i are integers from 0 to 4, g is an integer between 0 and 5. j is an integer between 0 and 3. R １ ~R ５ , and R Ｓ These may be the same or different from each other, and each may independently be hydrogen, deuterium, halogen group, cyano group, nitro group, amino group, C １ ~C ４０ alkyl group, C ２ ~C ４０ The alkenyl group, C ２ ~C ４０ The alkynyl group, C ３ ~C ４０ Cycloalkyl groups, heterocycloalkyl groups with 3 to 40 nuclear atoms, C ６ ~C ６０ aryl group, heteroaryl group with 5 to 60 nuclear atoms, C １ ~C ４０ The alkyloxy group, C ６ ~C ６０ The aryloxy group, C １ ~C ４０ alkylsilyl group, C ６ ~C ６０ The arylsilyl group, C １ ~C ４０ alkylboron group, C ６ ~C ６０ The arylboron group, C ６ ~C ６０ The arylphosphine group, C ６ ~C ６０ The arylphosphine oxide group and C ６ ~C ６０ Selected from the group consisting of arylamine groups, The above R １ ~R ５ , and R Ｓ The 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, and arylamine group are each independently deuterium, halogen, cyano group, nitro group, C ２ ~C ４０ The alkenyl group, C ２ ~C ４０ The alkynyl group, C ３ ~C ４０ Cycloalkyl groups, heterocycloalkyl groups with 3 to 40 nuclear atoms, C １ ~C ４０ alkyl group, C ６ ~C ６０ aryl group, heteroaryl group with 5 to 60 nuclear atoms, C １ ~C ４０ The alkyloxy group, C ６ ~C ６０ The aryloxy group, C １ ~C ４０ alkylsilyl group, C ６ ~C ６０ The arylsilyl group, C １ ~C ４０ alkylboron group, C ６ ~C ６０ The arylboron group, C ６ ~C ６０ The arylphosphine group, C ６ ~C ６０ The arylphosphine oxide group and C ６ ~C ６０ The substituents may be substituted or unsubstituted with one or more substituents selected from the group consisting of arylamine groups, and if there are multiple substituents, they may be identical or different from one another.

6. The compound represented by the above chemical formula 1 is selected from the group consisting of A-1 to C-126 below, according to claim 1: 【Chemistry 27】 【Chemistry 28】 【Chemistry 29】 【Transformation 30】 【Chemistry 31】 【Chemistry 32】 【Transformation 33】 【Transformation 34】 【Chemistry 35】 【Transformation 36】 【Chemistry 37】 【Transformation 38】

7. It includes an anode, a cathode, and one or more organic layers interposed between the anode and the cathode. An organic EL element wherein at least one of the one or more organic layers described above contains the organic compound described in any one of claims 1 to 6.

8. The organic EL element according to claim 7, wherein the organic layer containing the above-mentioned organic compound is an electron transport layer.

9. Anode and cathode positioned spaced apart from each other; Multiple light-emitting units interposed between the anode and cathode; and A charge generation layer interposed between adjacent light-emitting units, comprising an N-type charge generation layer and a P-type charge generation layer; Includes, Each of the above light-emitting units includes a hole transport layer, a light-emitting layer, and an electron transport layer. The above-mentioned N-type charge generation layer comprises an organic compound according to any one of claims 1 to 6, making it an organic EL element.

10. The above N-type charge generation layer includes one host having electron transport properties, The organic EL element according to claim 9, wherein the one host is an organic compound according to any one of claims 1 to 6.

11. The organic EL element according to claim 10, wherein the above-mentioned N-type charge generation layer further comprises an N-type dopant.

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