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KR-102959267-B1 - HETEROCYCLIC COMPOUND, ORGANIC LIGHT-EMITTING DEVICE AND COMPOSITION FOR ORGANIC MATERIAL LAYER OF ORGANIC LIGHT-EMITTING DEVICE COMPRISING SAME

KR102959267B1KR 102959267 B1KR102959267 B1KR 102959267B1KR-102959267-B1

Abstract

The present specification provides a heterocyclic compound, an organic light-emitting device comprising the same, and a composition for an organic layer of an organic light-emitting device.

Inventors

  • 이기백
  • 모준태
  • 김동준
  • 김용우
  • 최대혁

Assignees

  • 엘티소재주식회사

Dates

Publication Date
20260508
Application Date
20221024

Claims (16)

  1. Heterocyclic compounds represented by the following chemical formula 1: [Chemical Formula 1] In the above chemical formula 1, X is O, S, or -C(Ra)(Rb), and said Ra and Rb are the same or different from each other, and each is independently a substituted or unsubstituted C1 to C60 alkyl group or a substituted or unsubstituted C6 to C60 aryl group, and L is a direct bond; or a substituted or unsubstituted C6 to C60 arylene group, and n is an integer from 1 to 3, and when n is 2 or greater, the substituents within the parentheses are the same or different from each other, and Y1 is CR11 or N, Y2 is CR12 or N, Y3 is CR13 or N, Y4 is CR14 or N, Y5 is CR15 or N, and at least two of Y1 to Y5 are N. The above R11 to R15 are the same or different from each other, and each independently is hydrogen; deuterium; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group, or two or more adjacent groups are combined to form a substituted or unsubstituted C2 to C60 heterocycle, and Ar1 is a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group, and R1 and R2 are the same or different from each other, and each is independently hydrogen; or deuterium, and a is an integer from 0 to 4, and if a is 2 or greater, the substituents within the parentheses are the same or different, and b is an integer from 0 to 4, and if b is 2 or greater, the substituents in parentheses are the same or different.
  2. A heterocyclic compound according to claim 1, wherein the chemical formula 1 is represented by any one of the following chemical formulas 1-1 and 1-2: [Chemical Formula 1-1] [Chemical Formula 1-2] In the above chemical formulas 1-1 and 1-2, The definitions of X, R1 and R2, L, Y1 to Y5, a, b and n are the same as the definitions in Chemical Formula 1 above, and X3 is O or S, and Ar2 is a substituted or unsubstituted C6 to C60 aryl group, and R4 is each independently hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted C1 to C60 alkyl 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; or a substituted or unsubstituted C2 to C60 heteroaryl group, or two or more adjacent groups are combined to form a substituted or unsubstituted aliphatic or aromatic hydrocarbon ring or a heterocycle, and d is an integer from 0 to 7, and if d is 2 or greater, the substituents in parentheses are the same or different.
  3. A heterocyclic compound according to claim 1, wherein Ar1 is a substituted or unsubstituted C6 to C20 aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group.
  4. A heterocyclic compound according to claim 1, wherein L is a direct bond; or a substituted or unsubstituted C6 to C20 arylene group.
  5. A heterocyclic compound according to claim 1, wherein the chemical formula 1 is represented by any one of the following chemical formulas 1-3 to 1-6: [Chemical Formula 1-3] [Chemical Formula 1-4] [Chemical Formula 1-5] [Chemical Formula 1-6] In the above chemical formulas 1-3 to 1-6, The definitions of X, Ar1, R1, R2, L, a, b, and n are the same as the definitions in Chemical Formula 1 above, and X2 is O or S, and R51 to R59 are the same or different from one another and are each independently hydrogen; deuterium; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group, and R6 is hydrogen; deuterium; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group, and f is an integer from 0 to 4, and if f is 2 or greater, the substituents in parentheses are the same or different.
  6. A heterocyclic compound according to claim 1, wherein the deuterium content of the heterocyclic compound of formula 1 is 0% or 10% to 100%.
  7. A heterocyclic compound according to claim 1, wherein the chemical formula 1 is represented by any one of the following compounds: .
  8. An organic light-emitting device comprising: a first electrode; a second electrode provided opposite to the first electrode; and one or more organic layers provided between the first electrode and the second electrode, wherein one or more of the organic layers comprise a heterocyclic compound according to any one of claims 1 to 7.
  9. An organic light-emitting device according to claim 8, wherein the organic layer further comprises a heterocyclic compound represented by the following chemical formula 2: [Chemical Formula 2] In the above chemical formula 2, X1 is O or S, and R20 is hydrogen; deuterium; halogen; cyano group; 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, and t is an integer from 1 to 4, and if t is 2 or greater, the substituents within the parentheses are the same or different, and Ar2 and Ar3 are the same or different from each other and are each independently substituted or unsubstituted C6 to C60 aryl groups; or substituted or unsubstituted C2 to C60 heteroaryl groups, and R16 and R17 are the same or different from each other and are each independently substituted or unsubstituted C6 to C60 aryl groups; or substituted or unsubstituted C2 to C60 heteroaryl groups.
  10. An organic light-emitting device according to claim 9, wherein the deuterium content of the heterocyclic compound represented by Chemical Formula 2 is 0% to 100%.
  11. An organic light-emitting device according to claim 9, wherein the chemical formula 2 is represented by any one of the following compounds: .
  12. An organic light-emitting device according to claim 8, wherein the organic layer comprises a light-emitting layer, and the light-emitting layer comprises a heterocyclic compound represented by the chemical formula 1.
  13. An organic light-emitting device according to claim 8, wherein the organic layer comprises a light-emitting layer, the light-emitting layer comprises a host material, and the host material comprises a heterocyclic compound represented by the chemical formula 1.
  14. The organic light-emitting device of claim 8, wherein the organic light-emitting device further comprises one or more layers selected from the group consisting of a light-emitting layer, a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer, and an electron injection layer.
  15. A composition for an organic layer of an organic light-emitting device comprising: a heterocyclic compound represented by Formula 1 according to any one of claims 1 to 7; and a compound represented by the following Formula 2: [Chemical Formula 2] In the above chemical formula 2, X1 is O or S, and R20 is hydrogen; deuterium; halogen; cyano group; 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, and t is an integer from 1 to 4, and if t is 2 or greater, the substituents within the parentheses are the same or different, and Ar2 and Ar3 are the same or different from each other and are each independently substituted or unsubstituted C6 to C60 aryl groups; or substituted or unsubstituted C2 to C60 heteroaryl groups, and R16 and R17 are the same or different from each other and are each independently substituted or unsubstituted C6 to C60 aryl groups; or substituted or unsubstituted C2 to C60 heteroaryl groups.
  16. In claim 15, A composition for an organic layer of an organic light-emitting device, wherein the weight ratio of the heterocyclic compound represented by Formula 1 to the heterocyclic compound represented by Formula 2 in the composition is 1:10 to 10:1.

Description

Heterocyclic compound, organic light-emitting device comprising the same, and composition for organic material layer of organic light-emitting device The present invention relates to a heterocyclic compound, an organic light-emitting device containing the same, and a composition for an organic layer of an organic light-emitting device. Electroluminescent devices are a type of self-emissive display device that has the advantages of a wide viewing angle, excellent contrast, and fast response speed. An organic light-emitting diode has a structure in which an organic thin film is placed between two electrodes. When voltage is applied to an organic light-emitting diode with such a structure, electrons and holes injected from the two electrodes combine in the organic thin film to form pairs and then annihilate, emitting light. The organic thin film can be composed of a single layer or multiple layers as needed. The materials of organic thin films may possess luminescence capabilities as needed. For example, compounds capable of independently constituting an emissive layer may be used as organic thin film materials, or compounds capable of acting as a host or dopant in a host-dopant emissive layer may be used. In addition, compounds capable of performing functions such as hole injection, hole transport, electron blocking, and electron injection may also be used as organic thin film materials. To improve the performance, efficiency, and lifespan of organic light-emitting diodes, the development of organic thin film materials is continuously required. FIGS. 1 to 3 are schematic diagrams illustrating the stacked structure of an organic light-emitting device according to one embodiment of the present application. The present specification will be described in more detail below. In this specification, when a part is described as "comprising" a certain component, this means that, unless specifically stated otherwise, it does not exclude other components but may include additional components. In this specification, of the chemical formula means the position where it is combined. The term "substitution" above means that a hydrogen atom bonded to a carbon atom of a compound is replaced with another substituent, and the substitution site is not limited to the site where the hydrogen atom is substituted, that is, any site where a substituent can be substituted, and in the case of two or more substitutions, the two or more substituents may be the same or different from each other. In this specification, "substituted or unsubstituted" means deuterium; halogen group; -CN; C1 to C60 alkyl group; C2 to C60 alkenyl group; C2 to C60 alkynyl group; C1 to C60 haloalkyl group; C1 to C60 alkoxy group; C6 to C60 aryloxy group; C1 to C60 alkylthioxy group; C6 to C60 arylthioxy group; C1 to C60 alkyl sulfoxy group; C6 to C60 aryl sulfoxy group; C3 to C60 cycloalkyl group; C2 to C60 heterocycloalkyl group; C6 to C60 aryl group; C2 to C60 heteroaryl group; It means that one or more substituents selected from the group consisting of -SiRR'R"; -P(=O)RR'; and -NRR', or two or more substituents selected from the examples above are connected to a substituent, and R, R' and R" are each independently substituents consisting of at least one of hydrogen; deuterium; halogen group; alkyl group; alkenyl group; alkoxy group; cycloalkyl group; heterocycloalkyl group; aryl group; and heteroaryl group. In this specification, "where no substituent is indicated in the chemical formula or compound structure" means that hydrogen atoms are bonded to carbon atoms. However, since deuterium ( 2H ) is an isotope of hydrogen, some hydrogen atoms may be deuterium. In one embodiment of the present application, "where no substituents are indicated in the chemical formula or compound structure" may mean that all positions where substituents may be present are hydrogen or deuterium. That is, in the case of deuterium, it is an isotope of hydrogen, and some hydrogen atoms may be deuterium isotopes, and in this case, the content of deuterium may be 0% to 100%. In one embodiment of the present application, where "substituents are not indicated in the chemical formula or compound structure," if the deuterium content is 0%, the hydrogen content is 100%, and all substituents do not explicitly exclude hydrogen or other deuterium, hydrogen and deuterium may be used in a mixture in the compound. In one embodiment of the present application, deuterium is one of the isotopes of hydrogen and is an element having a deuteron, consisting of one proton and one neutron, as its nucleus, which can be represented as hydrogen-2, and its element symbol may be written as D or 2 H. In one embodiment of the present application, an isotope, which means an atom having the same atomic number (Z) but different mass number (A), can also be interpreted as an element having the same number of protons but different number of neutrons. In one embodiment of the present application, the meaning of the conte