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KR-102962923-B1 - HETEROCYCLIC COMPOUND, ORGANIC LIGHT EMITTING DEVICE COMPRISING SAME AND AND COMPOSITION FOR ORGANIC LAYER OF ORGANIC LIGHT EMITTING DEVICE

KR102962923B1KR 102962923 B1KR102962923 B1KR 102962923B1KR-102962923-B1

Abstract

The present application provides a heterocyclic compound capable of significantly improving the lifespan, efficiency, electrochemical stability, and thermal stability of an organic light-emitting device, an organic light-emitting device comprising said heterocyclic compound, and a composition for an organic layer of an organic light-emitting device comprising said heterocyclic compound.

Inventors

  • 이현주
  • 노영석
  • 김동준

Assignees

  • 엘티소재주식회사

Dates

Publication Date
20260513
Application Date
20210817

Claims (16)

  1. An organic light-emitting device comprising an anode, a cathode, and one or more organic layers provided between the anode and the cathode, wherein one or more of the organic layers comprise a heterocyclic compound represented by the following chemical formula 1 and a heterocyclic compound represented by the following chemical formula 2: [Chemical Formula 1] [Chemical Formula 2] In the above chemical formulas 1 and 2, X1 is O; S; CRaRb; or NRc, and R1 to R4 are identical or different from one another, and each independently is hydrogen; deuterium; a halogen group; -CN; or a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, and a is an integer from 0 to 5, and if a is 2 or greater, R1 inside the parentheses are identical or different from each other, and b and c are each integers from 0 to 4, and if b is 2 or greater, R2 inside the parentheses are identical or different, and if c is 2 or greater, R3 inside the parentheses are identical or different, and d is an integer from 0 to 2, and when d is 2, R4 inside the parentheses are identical or different from each other, and Ar1 is a substituted or unsubstituted biphenyl group; a substituted or unsubstituted dibenzofuran group; or a substituted or unsubstituted dimethylfluorene group, and Ar2 is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, and The above Ra to Rc are identical or different from each other and are each independently a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; or a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, and Rd and Re are identical or different from each other and each independently hydrogen; deuterium; halogen group; -CN; substituted or unsubstituted C1 to C60 alkyl group; substituted or unsubstituted C2 to C60 alkenyl group; substituted or unsubstituted C2 to C60 alkynyl group; substituted or unsubstituted C1 to C20 alkoxy group; substituted or unsubstituted C3 to C60 cycloalkyl group; substituted or unsubstituted C2 to C60 heterocycloalkyl group; substituted or unsubstituted C6 to C60 aryl group; substituted or unsubstituted C2 to C60 heteroaryl group; -SiR31R32R33; -P(=O)R31R32; and selected from the group consisting of 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 substituted or unsubstituted amine group, or two or more adjacent groups are combined to form a substituted or unsubstituted aliphatic or aromatic hydrocarbon ring, and R21 and R22 are identical or different from each other, and each independently -SiR31R32R33; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, and R31, R32 and R33 are identical or different from each other and are each independently hydrogen; deuterium; -CN; a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, and r and s are integers from 0 to 7, and where r and s are each 2 or greater, the substituents within the parentheses are identical or different from each other, and When X1 is O, the heterocyclic compound represented by the above chemical formula 1 is represented by any one of the following chemical formulas 1-1 to 1-3, and [Chemical Formula 1-1] [Chemical Formula 1-2] [Chemical Formula 1-3] In the above chemical formulas 1-1 to 1-3, The definitions of X1, R1 to R4, a to d, Ar1 and Ar2 are the same as the definitions of the substituents in Chemical Formula 1 above.
  2. An organic light-emitting device according to claim 1, wherein the chemical formula 1 is represented by any one of the following chemical formulas 3 to 5: [Chemical Formula 3] [Chemical Formula 4] [Chemical Formula 5] In the above chemical formulas 3 to 5, R5 to R8 are identical or different from one another and are each independently hydrogen; deuterium; a halogen group; -CN; a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, and e is an integer from 0 to 4, and if e is 2 or greater, R5 within the parentheses are identical or different from each other, and f is an integer from 0 to 5, and if f is 2 or greater, R6 inside the parentheses are identical or different from each other, and g and h are each integers from 0 to 7, and if g is 2 or greater, R7 within the parentheses are identical or different, and if h is 2 or greater, R8 within the parentheses are identical or different, and The definitions of X1, R1 to R4, a to d, and Ar2 are the same as the definitions of the substituents in Chemical Formula 1.
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  5. In claim 1, the deuterium content of the heterocyclic compound represented by Formula 1 is 10% to 100%, and An organic light-emitting device in which the above deuterium content is calculated as T2/T1 × 100 (%) based on the number of substituents containing deuterium (T2) among the total number of substituents (T1) in the heterocyclic compound of Chemical Formula 1.
  6. In claim 1, the deuterium content of the heterocyclic compound represented by Formula 2 is 10% to 100%, and An organic light-emitting device in which the above deuterium content is calculated as T2/T1 × 100 (%) based on the number of deuterium-containing substituents (T2) among the total number of substituents (T1) in the heterocyclic compound of Chemical Formula 2.
  7. Organic light-emitting device comprising a compound represented by any one of the following compounds:
  8. An organic light-emitting device according to claim 1, wherein the chemical formula 2 is represented by any one of the following compounds:
  9. An organic light-emitting device according to claim 1, wherein the organic layer comprises one or more light-emitting layers, and the light-emitting layer comprises a heterocyclic compound represented by Formula 1 and a heterocyclic compound represented by Formula 2.
  10. An organic light-emitting device according to claim 9, wherein the light-emitting layer comprises a host material, and the host material comprises a heterocyclic compound represented by Formula 1 and a heterocyclic compound represented by Formula 2.
  11. An organic light-emitting device according to claim 1, 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 injection layer, an electron transport layer, a hole assist layer, and a hole blocking layer.
  12. Heterocyclic compounds represented by the following chemical formulas 1-2 or 1-5: [Chemical Formula 1-2] [Chemical Formula 1-5] In the above chemical formulas 1-2 and 1-5, X1 is O; S; CRaRb; or NRc, and R1 to R4 are identical or different from one another, and each independently is hydrogen; deuterium; a halogen group; -CN; or a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, and a is an integer from 0 to 5, and if a is 2 or greater, R1 inside the parentheses are identical or different from each other, and b and c are each integers from 0 to 4, and if b is 2 or greater, R2 inside the parentheses are identical or different, and if c is 2 or greater, R3 inside the parentheses are identical or different, and d is an integer from 0 to 2, and when d is 2, R4 inside the parentheses are identical or different from each other, and Ar1 is a substituted or unsubstituted biphenyl group; a substituted or unsubstituted dibenzofuran group; or a substituted or unsubstituted dimethylfluorene group, and Ar2 is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, and The above Ra to Rc are identical or different from each other and are each independently a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; or a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, and When X1 is O, the above heterocyclic compound is represented by the above chemical formula 1-2.
  13. In claim 12, the deuterium content of the heterocyclic compound represented by Chemical Formula 1-2 is 10% or more and 100% or less, and A heterocyclic compound in which the above deuterium content is calculated as T2/T1 × 100 (%) based on the number of deuterium-containing substituents (T2) among the total number of substituents (T1) in the heterocyclic compound of Chemical Formula 1-2.
  14. In claim 12, the deuterium content of the heterocyclic compound represented by Chemical Formula 1-5 is 10% or more and 100% or less, and A heterocyclic compound in which the above deuterium content is calculated as T2/T1 × 100 (%) based on the number of substituents containing deuterium (T2) among the total number of substituents (T1) in the heterocyclic compound of Chemical Formula 1-5.
  15. A composition for an organic layer of an organic light-emitting device comprising a heterocyclic compound represented by the following chemical formula 1 and a heterocyclic compound represented by the following chemical formula 2: [Chemical Formula 1] [Chemical Formula 2] In the above chemical formulas 1 and 2, X1 is O; S; CRaRb; or NRc, and R1 to R4 are identical or different from one another, and each independently is hydrogen; deuterium; a halogen group; -CN; or a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, and a is an integer from 0 to 5, and if a is 2 or greater, R1 inside the parentheses are identical or different from each other, and b and c are each integers from 0 to 4, and if b is 2 or greater, R2 inside the parentheses are identical or different, and if c is 2 or greater, R3 inside the parentheses are identical or different, and d is an integer from 0 to 2, and when d is 2, R4 inside the parentheses are identical or different from each other, and Ar1 is a substituted or unsubstituted biphenyl group; a substituted or unsubstituted dibenzofuran group; or a substituted or unsubstituted dimethylfluorene group, and Ar2 is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, and The above Ra to Rc are identical or different from each other and are each independently a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; or a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, and Rd and Re are identical or different from each other and each independently hydrogen; deuterium; halogen group; -CN; substituted or unsubstituted C1 to C60 alkyl group; substituted or unsubstituted C2 to C60 alkenyl group; substituted or unsubstituted C2 to C60 alkynyl group; substituted or unsubstituted C1 to C20 alkoxy group; substituted or unsubstituted C3 to C60 cycloalkyl group; substituted or unsubstituted C2 to C60 heterocycloalkyl group; substituted or unsubstituted C6 to C60 aryl group; substituted or unsubstituted C2 to C60 heteroaryl group; -SiR31R32R33; -P(=O)R31R32; and selected from the group consisting of 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 substituted or unsubstituted amine group, or two or more adjacent groups are combined to form a substituted or unsubstituted aliphatic or aromatic hydrocarbon ring, and R21 and R22 are identical or different from each other, and each independently -SiR31R32R33; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, and R31, R32 and R33 are identical or different from each other and are each independently hydrogen; deuterium; -CN; a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, and r and s are integers from 0 to 7, and where r and s are each 2 or greater, the substituents within the parentheses are identical or different from each other, and When X1 is O, the heterocyclic compound represented by the above chemical formula 1 is represented by any one of the following chemical formulas 1-1 to 1-3, and [Chemical Formula 1-1] [Chemical Formula 1-2] [Chemical Formula 1-3] In the above chemical formulas 1-1 to 1-3, The definitions of X1, R1 to R4, a to d, Ar1 and Ar2 are the same as the definitions of the substituents in Chemical Formula 1 above.
  16. A composition for an organic layer of an organic light-emitting device according to claim 15, 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 an organic layer of an organic light-emitting device This specification relates to heterocyclic compounds, organic light-emitting devices containing the same, and compositions for organic layers of organic light-emitting devices. 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. Furthermore, 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, lifespan, or efficiency 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 application will be described in detail below. One embodiment of the present application provides an organic light-emitting device comprising an anode, a cathode, and one or more organic layers provided between the anode and the cathode, wherein one or more of the organic layers comprise a heterocyclic compound represented by the following chemical formula 1 and a heterocyclic compound represented by the following chemical formula 2. [Chemical Formula 1] [Chemical Formula 2] In the above chemical formulas 1 and 2, X1 is O; S; CRaRb; or NRc, and R1 to R4 are identical or different from one another, and each independently is hydrogen; deuterium; a halogen group; -CN; or a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, and a is an integer from 0 to 5, and if a is 2 or greater, R1 inside the parentheses are identical or different from each other, and b and c are each integers from 0 to 4, and if b is 2 or greater, R2 inside the parentheses are identical or different, and if c is 2 or greater, R3 inside the parentheses are identical or different, and d is an integer from 0 to 2, and when d is 2, R4 inside the parentheses are identical or different from each other, and Ar1 is a substituted or unsubstituted biphenyl group; a substituted or unsubstituted dibenzofuran group; or a substituted or unsubstituted dimethylfluorene group, and Ar2 is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, and The above Ra to Rc are identical or different from each other and are each independently a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; or a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, and Rd and Re are identical or different from each other and each independently hydrogen; deuterium; halogen group; -CN; substituted or unsubstituted C1 to C60 alkyl group; substituted or unsubstituted C2 to C60 alkenyl group; substituted or unsubstituted C2 to C60 alkynyl group; substituted or unsubstituted C1 to C20 alkoxy group; substituted or unsubstituted C3 to C60 cycloalkyl group; substituted or unsubstituted C2 to C60 heterocycloalkyl group; substituted or unsubstituted C6 to C60 aryl group; substituted or unsubstituted C2 to C60 heteroaryl group; -SiR31R32R33; -P(=O)R31R32; and selected from the group consisting of 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 substituted or unsubstituted amine group, or two or more adjacent groups are combined to form a substituted or unsubstituted aliphatic or aromatic hydrocarbon ring, and R21 and R22 are identical or different from each other, and each independently -SiR31R32R33; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, and R31, R32 and R33 are identical or different from each other and are each independently hydrogen; deuterium; -CN; a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstitute