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US-12617778-B2 - Heterocyclic compound, organic light-emitting element comprising same, composition for organic layer of organic light-emitting element, and method for producing organic light-emitting element

US12617778B2US 12617778 B2US12617778 B2US 12617778B2US-12617778-B2

Abstract

The present specification provides a heterocyclic compound represented by Chemical Formula 1, an organic light emitting device comprising the same, a composition for an organic material layer of an organic light emitting device, and a method for manufacturing an organic light emitting device.

Inventors

  • Yong-Hui Lee
  • Jun-Tae MO
  • Dong-Jun Kim

Assignees

  • LT MATERIALS CO., LTD.

Dates

Publication Date
20260505
Application Date
20201221
Priority Date
20191226

Claims (11)

  1. 1 . A heterocyclic compound represented by the following Chemical Formula 2 or Chemical Formula 3: wherein, in Chemical Formulae 2 and 3, X is O; or S; L is a direct bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group; R1 to R4 are the same as or different from each other, and each independently selected from the group consisting of hydrogen; deuterium; halogen; a cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; —P(═O) RR′; —SiRR′R″ and —NRR′, or two or more groups adjacent to each other bond to each other to form a substituted or unsubstituted C6 to C60 aliphatic or aromatic hydrocarbon ring or a substituted or unsubstituted C 2 to C60 aliphatic or aromatic heteroring; q and n are the same as or different from each other, and are each an integer of 0 to 4; m is an integer of 0 to 3; p is an integer of 0 to 2; a is an integer of 0 to 4; and Ar is represented by any one of the following Chemical Formula 1-1 to Chemical Formula 1-6, in Chemical Formulae 1-1 to 1-6, means a position linked to L of Chemical Formulae 2 and 3; R11 to R30 are the same as or different from each other, and each independently selected from the group consisting of hydrogen; deuterium; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; —P(═O) RR′; —SiRR′R″ and —NRR′; Ar2 and Ar3 are the same as or different from each other, and each independently a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group; Y is O; S; NRa; or CRbRc; and R, R′, R″ and Ra to Rc are the same as or different from each other, and each independently a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.
  2. 2 . The heterocyclic compound of claim 1 , wherein Chemical Formula 2 or 3 is represented by any one of the following compounds:
  3. 3 . An organic light emitting device comprising: a first electrode; a second electrode provided opposite to the first electrode; and one or more organic material layers provided between the first electrode and the second electrode, wherein the one or more organic material layers comprise the heterocyclic compound of claim 1 .
  4. 4 . The organic light emitting device of claim 3 , wherein the one or more organic material layers further comprise a heterocyclic compound represented by the following Chemical Formula 7: in Chemical Formula 7, La1 to La3 are the same as or different from each other, and each independently a direct bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group; Ra1 is a substituted or unsubstituted C6 to C60 aryl group; Ra2 and Ra3 are the same as or different from each other, and each independently selected from the group consisting of hydrogen; deuterium; halogen; a cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C 1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; and —NRR′, or two or more groups adjacent to each other bond to each other to form a substituted or unsubstituted C6 to C60 aliphatic or aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 aliphatic or aromatic heteroring; R and R′ are the same as or different from each other, and each independently a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group; a1 to a3 are an integer of 0 to 4; a11, a22 and a33 are an integer of 1 to 6; and when a1 to a3, a11, a22 and a33 are 2 or greater, substituents in the parentheses are the same as or different from each other.
  5. 5 . The organic light emitting device of claim 3 , wherein the one or more organic material layers comprise a light emitting layer, and the light emitting layer comprises the heterocyclic compound.
  6. 6 . The organic light emitting device of claim 3 , wherein the one or more organic material layers comprise a light emitting layer, the light emitting layer comprises a host material, and the host material comprises the heterocyclic compound.
  7. 7 . The organic light emitting device of claim 3 , further comprising one, two or more layers selected from the group consisting of a light emitting layer, a hole injection layer, a hole transfer layer, an electron injection layer, an electron transfer layer, an electron blocking layer and a hole blocking layer.
  8. 8 . A composition for an organic material layer of an organic light emitting device, the composition comprising: the heterocyclic compound of claim 1 ; and a heterocyclic compound represented by the following Chemical Formula 7: wherein, in Chemical Formula 7, La1 to La3 are the same as or different from each other, and each independently a direct bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C 2 to C60 heteroarylene group; Ra1 is a substituted or unsubstituted C6 to C60 aryl group; Ra2 and Ra3 are the same as or different from each other, and each independently selected from the group consisting of hydrogen; deuterium; halogen; a cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; and —NRR′, or two or more groups adjacent to each other bond to each other to form a substituted or unsubstituted C6 to C60 aliphatic or aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 aliphatic or aromatic heteroring; R and R′ are the same as or different from each other, and each independently a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group; a1 to a3 are an integer of 0 to 4; a11, a22 and a33 are an integer of 1 to 6; and when a1 to a3, a11, a22 and a33 are 2 or greater, substituents in the parentheses are the same as or different from each other.
  9. 9 . The composition of claim 8 , wherein the heterocyclic compound represented by Chemical Formula 2 or 3 and the heterocyclic compound represented by Chemical Formula 7 have a weight ratio of 1:10 to 10:1 in the composition.
  10. 10 . A method for manufacturing an organic light emitting device, the method comprising: preparing a substrate; forming a first electrode on the substrate; forming one or more organic material layers on the first electrode; and forming a second electrode on the one or more organic material layers, wherein the forming of the one or more organic material layers is performed by using the composition of claim 8 .
  11. 11 . The method of claim 10 , wherein the forming of the one or more organic material layers is performed by using a thermal vacuum deposition method after pre-mixing the heterocyclic compound of Chemical Formula 2 or 3 and the heterocyclic compound of Chemical Formula 7.

Description

TECHNICAL FIELD This application claims priority to and the benefits of Korean Patent Application No. 10-2019-0174983, filed with the Korean Intellectual Property Office on Dec. 26, 2019, the entire contents of which are incorporated herein by reference. The present specification relates to a heterocyclic compound, an organic light emitting device comprising the same, a composition for an organic material layer of an organic light emitting device, and a method for manufacturing an organic light emitting device. BACKGROUND ART An organic electroluminescent device is one type of self-emissive display devices, and has an advantage of having a wide viewing angle, and a high response speed as well as having an excellent contrast. An organic light emitting device has a structure disposing an organic thin film between two electrodes. When a voltage is applied to an organic light emitting device having such a structure, electrons and holes injected from the two electrodes bind and pair in the organic thin film, and light emits as these annihilate. The organic thin film may be formed in a single layer or a multilayer as necessary. A material of the organic thin film may have a light emitting function as necessary. For example, as a material of the organic thin film, compounds capable of forming a light emitting layer themselves alone may be used, or compounds capable of performing a role of a host or a dopant of a host-dopant-based light emitting layer may also be used. In addition thereto, compounds capable of performing roles of hole injection, hole transfer, electron blocking, hole blocking, electron transfer, electron injection and the like may also be used as a material of the organic thin film. Development of an organic thin film material has been continuously required for enhancing performance, lifetime or efficiency of an organic light emitting device. Studies on an organic light emitting device comprising a compound capable of satisfying conditions required for materials usable in an organic light emitting device, for example, satisfying proper energy level, electrochemical stability, thermal stability and the like, and having a chemical structure capable of performing various roles required in an organic light emitting device depending on substituents have been required. PRIOR ART DOCUMENTS Patent Documents U.S. Pat. No. 4,356,429 DISCLOSURE Technical Problem The present application relates to a heterocyclic compound, an organic light emitting device comprising the same, a composition for an organic material layer of an organic light emitting device, and a method for manufacturing an organic light emitting device. Technical Solution One embodiment of the present application provides a heterocyclic compound represented by the following Chemical Formula 1. In Chemical Formula 1, X is O; or S,L is a direct bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group,R1 to R4 are the same as or different from each other, and each independently selected from the group consisting of hydrogen; deuterium; halogen; a cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; —P(═O)RR′; —SiRR′R″ and —NRR′, or two or more groups adjacent to each other bond to each other to form a substituted or unsubstituted C6 to C60 aliphatic or aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 aliphatic or aromatic heteroring,q and n are the same as or different from each other, and are each an integer of 0 to 4,m is an integer of 0 to 3,p is an integer of 0 to 2,a is an integer of 0 to 4, andAr is represented by any one of the following Chemical Formula 1-1 to Chemical Formula 1-6, in Chemical Formulae 1-1 to 1-6, means a position linked to L of Chemical Formula 1,R11 to R30 are the same as or different from each other, and each independently selected from the group consisting of hydrogen; deuterium; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; —P(═O)RR′; —SiRR′R″ and —NRR′,Ar2 and Ar3 are the same as or different from each other, and each independently a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group,Y is O; S; NRa; or CRbRc, andR, R′, R″ and Ra to Rc are the same as or different from each other, and each independently a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2