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KR-102963990-B1 - COMPOUND, ORGANIC LIGHT EMITTING DEVICE AND COMPOSITION FOR ORGANIC LIGHT EMITTING DEVICE

KR102963990B1KR 102963990 B1KR102963990 B1KR 102963990B1KR-102963990-B1

Abstract

The present specification provides a compound organic light-emitting diode and a composition for an organic light-emitting diode.

Inventors

  • 이영진
  • 모준태
  • 김동준
  • 최대혁

Assignees

  • 엘티소재주식회사

Dates

Publication Date
20260513
Application Date
20230315

Claims (18)

  1. Compound represented by the following chemical formula 1: [Chemical Formula 1] In the above chemical formula 1, X1 is O; S; or NRa, and Y1 is N; or CRb, and Y2 is N; or CRc, and Y3 is N; or CRd, and Y4 is N; or CRe, and Two of Y1 to Y4 are N, and R1, R2 and Ra are identical or different from each other and are each independently selected from the group consisting of hydrogen; deuterium; halogen; -CN; substituted or unsubstituted C1 to C60 alkyl groups; substituted or unsubstituted C1 to C60 alkoxy groups; substituted or unsubstituted C3 to C60 cycloalkyl groups; substituted or unsubstituted C2 to C60 heterocycloalkyl groups; substituted or unsubstituted C6 to C60 aryl groups; substituted or unsubstituted C2 to C60 heteroaryl groups; -SiRR'R"; and -P(=O)RR', and Rb to Re are identical or different from one another, and each is independently a phenyl group substituted or unsubstituted with deuterium; a biphenyl group substituted or unsubstituted with deuterium; or a naphthyl group substituted or unsubstituted with deuterium, and R, R' and R" are identical or different from each other and are each independently hydrogen; deuterium; -CN; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group, and R3 is represented by the following structural formula A or B, and [Structural Formula A] [Structural Formula B] In the above structural formulas A and B, represents the connection position, and L1 is a direct bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group, and L33 and L44 are identical or different from each other and are each independently directly bonded; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group, and Ar33 and Ar44 are identical 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 R4 is selected from the group consisting of hydrogen; deuterium; a substituted or unsubstituted C6 to C60 aryl group; and a substituted or unsubstituted C2 to C60 heteroaryl group, or two or more adjacent groups are bonded to form a ring, a is 1 or 2, and b is an integer from 1 to 3, and c is 1 or 2, and d is an integer from 1 to 8, and m is 1 or 2, and If each of a, b, c, d, and m is 2 or an integer greater than or equal to 2, the substituents within each parenthesis are identical or different from each other, and “Substituted or unsubstituted” means substituted or unsubstituted with deuterium; C6 to C60 aryl groups; or C2 to C60 heteroaryl groups.
  2. In claim 1, The above chemical formula 1 is a compound represented by any one of the following chemical formulas 1-1 to 1-4: [Chemical Formula 1-1] [Chemical Formula 1-2] [Chemical Formula 1-3] [Chemical Formula 1-4] In the above chemical formulas 1-1 to 1-4, X1, Y1 to Y4, R1 to R3, a and b are identical to the definitions in Chemical Formula 1 above.
  3. In claim 1, The above chemical formula 1 is a compound represented by any one of the following chemical formulas 1-5 to 1-7: [Chemical Formula 1-5] [Chemical Formula 1-6] [Chemical Formula 1-7] In the above chemical formulas 1-5 to 1-7, X1, Y1 to Y4, R1 to R3, a, b, and c are identical to the definitions in Chemical Formula 1 above.
  4. In claim 1, The above chemical formula 1 is a compound represented by any one of the following chemical formulas 1-10 to 1-15: [Chemical Formula 1-10] [Chemical Formula 1-11] [Chemical Formula 1-12] [Chemical Formula 1-13] [Chemical Formula 1-14] [Chemical Formula 1-15] In the above chemical formulas 1-10 to 1-15, X1, Y1 to Y4, R1 to R3, a, b, and c are identical to the definitions in Chemical Formula 1 above.
  5. In claim 1, R1 and R2 are the same or different from each other, and each independently is a compound that is hydrogen; or deuterium.
  6. In claim 1, A compound having a deuterium substitution rate of 0% or 1% to 100%.
  7. delete
  8. Compounds represented by any one of the following compounds: .
  9. An organic light-emitting device comprising: a first electrode; a second electrode; and an organic layer provided between the first electrode and the second electrode, wherein the organic layer comprises a compound according to any one of claims 1 to 6 and 8.
  10. In claim 9, An organic light-emitting device in which the above organic layer further comprises a heterocyclic compound represented by the following chemical formula A: [Chemical Formula A] In the above chemical formula A, X2 is O; or S, and R22 is selected from the group consisting of hydrogen; deuterium; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; and -NRR', or two adjacent groups are bonded to each other to form a ring, and N-Het is substituted or unsubstituted with a substituent selected from the group consisting of deuterium, aryl groups and -P(=O)RR', and is a monocyclic or polycyclic C2 to C60 heteroaryl group containing one or more N, R and R' are identical 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 i is an integer from 1 to 7, and if i is an integer greater than or equal to 2, R22 are identical or different from each other, and t is 1 or 2, and when t is 2, N-Het are identical or different, and “Substituted or unsubstituted” means substituted or unsubstituted with deuterium; C6 to C60 aryl groups; or C2 to C60 heteroaryl groups.
  11. In claim 10, An organic light-emitting device in which the above chemical formula A is represented by any one of the following chemical formulas A-1 to A-3: [Chemical Formula A-1] [Chemical Formula A-2] [Chemical Formula A-3] In the above chemical formulas A-1 to A-3, R23 to R25 are identical or different from one another and are each independently selected from the group consisting of hydrogen; deuterium; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; and -NRR', f is an integer from 1 to 7, and if f is an integer greater than or equal to 2, R23 are identical or different from each other, and g and h are identical or different from each other, and each is independently an integer from 1 to 9, and where each g and h is an integer of 2 or more, the substituents within the parentheses are identical or different from each other, and X2, N-Het, R, R' and t are as defined in the above chemical formula A.
  12. An organic light-emitting device comprising: a first electrode; a second electrode; and an organic layer provided between the first electrode and the second electrode, wherein the organic layer comprises a compound according to any one of claims 1 to 6 and 8; and a heterocyclic compound represented by any one of the following compounds: .
  13. In claim 9, An organic light-emitting device in which the above organic layer comprises a light-emitting layer, and the light-emitting layer comprises the above compound.
  14. In claim 9, An organic light-emitting device wherein the organic layer comprises a light-emitting layer, the light-emitting layer comprises a host material, and the host material comprises the compound.
  15. In claim 9, The above 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, a hole blocking layer, an electron blocking layer, a hole transport assisting layer, an electron transport layer, and an electron injection layer.
  16. A compound according to any one of claims 1 to 6 and 8; and Composition for an organic light-emitting device comprising a heterocyclic compound represented by the following chemical formula A: [Chemical Formula A] In the above chemical formula A, X2 is O; or S, and R22 is selected from the group consisting of hydrogen; deuterium; halogen; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; and -NRR', or two adjacent groups are bonded to each other to form a ring, N-Het is substituted or unsubstituted with a substituent selected from the group consisting of deuterium, aryl groups and -P(=O)RR', and is a monocyclic or polycyclic C2 to C60 heteroaryl group containing one or more N, R and R' are identical 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 i is an integer from 1 to 7, and if i is 2 or greater, R22 are identical or different from each other, and t is 1 or 2, and when t is 2, N-Het are the same or different. “Substituted or unsubstituted” means substituted or unsubstituted with deuterium; C6 to C60 aryl groups; or C2 to C60 heteroaryl groups.
  17. In claim 16, A composition for an organic light-emitting device in which the weight ratio of the above compound and the heterocyclic compound represented by the above chemical formula A is 1:10 to 10:1.
  18. In claim 16, The deuterium substitution rate of the above compound is 0% or 1% to 100%, and A composition for an organic light-emitting device in which the deuterium substitution rate of the heterocyclic compound represented by the above chemical formula A is 0% or 1% to 100%.

Description

Compound, Organic Light Emitting Device and Composition for Organic Light Emitting Device This specification relates to compounds, organic light-emitting diodes, and compositions for organic light-emitting diodes. 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 4 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 a position that is bonded to another substituent or bonding site. 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 content T% of a specific substituent can be defined as T2/T1X100 = T% when the total number of sub