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 specifically to an organic compound having excellent heat resistance, carrier transport ability, light emitting ability, etc., and an organic electroluminescence device in which various properties such as light emitting efficiency, driving voltage, and life are improved by including the organic compound in one or more organic layers.

Claims

1. A compound represented by the following formula 1. 【Chemistry 1】 (In the formula, X １ ~X ３ may be the same or different, and each independently represents N or C(Ar ３ ), where X １ ~X ３ At least one of the groups is N, and C(Ar ３ When there are a plurality of Ar ３ may be the same or different from each other, Ar １ ~Ar ３ 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; 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 or are joined to adjacent groups to form a fused ring; n is an integer from 0 to 3, L １ is a single bond, or C ６ ~C ６０ and heteroarylene groups having 5 to 60 ring atoms, R １ ~R ３ may be the same or different, and each independently represents C ６ ~C ６０ and heteroaryl groups having 5 to 60 ring atoms, However, R １ ~R ３ At least one of the above is a substituent represented by any one of the following formulas 2 to 6: 【Chemistry 2】 (In the formula, Y １ is C(Ar ４ ) (Ar ５ ), N(Ar ６ ), O, and S; Y ２ and Y ３ may be the same or different and are each independently O or S; Ring A is a benzene ring; L ２ is a single bond, or C ６ ~C ６０ and heteroarylene groups having 5 to 60 ring atoms, a, c, i, and j each represent an integer from 0 to 4; b is an integer from 0 to 3; d, e, and f each represent an integer from 0 to 5; g is an integer from 0 to 8; h is an integer from 0 to 9; Ar ４ ~Ar ６ and R ４ ~R １３ 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; 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 and wherein the aryl amine group is selected from the group consisting of The above Ar １ ~Ar ３ an alkyl group, an alkenyl group, an alkynyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an alkyloxy group, an aryloxy group, an alkylsilyl group, an arylsilyl group, an alkylboron group, an arylboron group, an arylphosphine group, an arylphosphine oxide group, an arylamine group, and a fused ring; １ arylene groups and heteroarylene groups represented by the above R １ ~R ３ The aryl and heteroaryl groups of the above Ar ４ ~Ar ６ , and R ４ ~R １３ 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, and the arylamine group 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; 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 group may be substituted or unsubstituted with one or more substituents selected from the group consisting of the arylamine groups of the formula (I), and when there are a plurality of the above substituents, they may be the same or different.

2. The compound according to claim 1, wherein the substituent represented by any one of the formulas 2 to 6 is selected from the group consisting of the following substituents S1-1 to S1-16. 【Chemistry 3】

3. R １ ~R ３ Any one of the above is a substituent represented by any one of the above formulas 2 to 6, and the remaining ones may be the same or different, and each independently represents ６ ~C ６０ The compound according to claim 1 , wherein the aryl group is

4. The compound according to claim 1, wherein the compound represented by Chemical Formula 1 is represented by any one of Chemical Formulas 7 to 11 below. 【Chemistry 4】 【change】 (In the formula, R ２ ~R １３ , a, b, c, d, e, f, g, h, i, j, X １ ~X ３ , Ar １ , Ar ２ , n, L １ , L ２ , Y １ ~Y ３ and ring A are each as defined in claim 1.

5. The compound according to claim 1, wherein the compound represented by Chemical Formula 1 is represented by any one of Chemical Formulas 12 to 16 below. 【Chemistry 5】 【change】 (In the formula, R ２ ~R １３ , a, b, c, d, e, f, g, h, i, j, X １ ~X ３ , Ar １ , Ar ２ , n, L １ , Y １ ~Y ３ and ring A are each as defined in claim 1; k and l each represent an integer from 0 to 5; R １４ and R １５ may be the same or different, and each independently represents deuterium, a halogen, a cyano group, a 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; 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 are selected from the group consisting of:

6. L １ The compound of claim 1 , wherein is selected from the group consisting of a direct bond or a phenylene group, a biphenylene group, a terphenylene group, and a naphthalene group.

7. L １ is a direct bond or any one of the following linker groups L-1 to L-6: 【Chemistry 6】 (In the formula, * is the site where the bond with Chemical Formula 1 is formed. A plurality of m's may be the same or different, m is an integer from 0 to 4, Multiple R １９ may be the same or different from each other, R １９ is a 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; 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 are selected from the group consisting of:

8. X １ ~X ３ The compound according to claim 1, wherein the containing ring is any one of the following structural formulas Az1-1 to Az1-7: 【Chemistry 7】 (In the formula, Ar １ and Ar ２ may be the same or different, and each independently represents １ ~C ４０ Alkyl groups of C ３ ~C ４０ a cycloalkyl group having 3 to 40 ring atoms; ６ ~C ６０ and heteroaryl groups having 5 to 60 ring atoms, Z １ ~Z ４ are C(Ar ７ ) (Ar ８ ), N(Ar ９ ), O, and S; Ar ７ ~Ar ９ 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; 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 and wherein the aryl amine group is selected from the group consisting of The above Ar １ and Ar ２ alkyl groups, cycloalkyl groups, heterocycloalkyl groups, aryl groups, and heteroaryl groups, as well as Ar ７ ~Ar ９ 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, and the arylamine group 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; 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 group may be substituted or unsubstituted with one or more substituents selected from the group consisting of the arylamine groups of the formula (I), and when there are a plurality of the above substituents, they may be the same or different.

9. The compound according to claim 1, wherein the compound represented by Chemical Formula 1 is represented by any one of Chemical Formulas 17 to 21 below. 【Chemistry 8】 【change】 (In the formula, R ２ ~R １３ , a, b, c, d, e, f, g, h, i, j, X １ ~X ３ , Ar １ , Ar ２ , Y １ ~Y ３ and ring A are each as defined in claim 1; n1 is an integer from 0 to 2, k and l each represent an integer from 0 to 5; Multiple R １４ may be the same or different from each other, Multiple R １５ may be the same or different from each other, R １４ and R １５ may be the same or different, and each independently represents deuterium, a halogen, a cyano group, a 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 are selected from the group consisting of:

10. The compound according to claim 1, wherein the compound represented by Chemical Formula 1 is any one of the following compounds Inv1 to Inv480. 【Chemistry 9】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】

11. an anode; a cathode; and one or more organic layers interposed between the anode and the cathode; An organic electroluminescence device, wherein at least one of the one or more organic layers comprises the compound according to any one of claims 1 to 10.

12. 12. The organic electroluminescence device according to claim 11, wherein the organic layer containing the compound is at least one selected from the group consisting of a light-emitting layer, an electron transport layer, and an electron transport auxiliary layer.

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