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EP-4036091-B1 - HETEROCYCLIC COMPOUND AND ORGANIC LIGHT-EMITTING DEVICE COMPRISING SAME

EP4036091B1EP 4036091 B1EP4036091 B1EP 4036091B1EP-4036091-B1

Inventors

  • KIM, JI-YOUNG
  • MO, Jun-Tae
  • KIM, DONG-JUN

Dates

Publication Date
20260506
Application Date
20200924

Claims (9)

  1. A heterocyclic compound represented by the following Chemical Formula 1-1 or 1-2: wherein, in Chemical Formulae 1-1 and 1-2, L1 and L2 are each independently a direct bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted divalent C2 to C60 heterocyclic group, Ar1 is selected from among the following structural formulae, in the structural formulae, X is O; S; or NR, Z11 to Z13 are each independently CR' or N, and at least two thereof are N, R, R' and R11 to R13 are each independently hydrogen; deuterium; a halogen group; 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 heterocyclic group, r11 is 1 or 2, r12 and r13 are each independently an integer of 1 to 5, and when r11 is 2 and r12 and r13 are each an integer of 2 or greater, substituents in the parentheses are the same as or different from each other, Ar2 is -N(R106) (R107); or represented by the following Chemical Formula 4, in Chemical Formula 4, R4 is hydrogen; deuterium; a halogen group; 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 heterocyclic group, or two or more groups adjacent to each other bond to each other to form a substituted or unsubstituted C3 to C60 aliphatic hydrocarbon ring; a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring; or a C2 to C60 heteroring, r4 is an integer of 1 to 8, and when r4 is 2 or greater, substituents in the parentheses are the same as or different from each other, R1 and R2 are each independently hydrogen; deuterium; a halogen group; 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 heterocyclic group, R106 and R107 are each independently hydrogen; deuterium; a halogen group; an alkyl group; an alkenyl group; an alkoxy group; a cycloalkyl group; an aryl group; or a heterocyclic group, r1 is an integer of 1 to 4, r2 is an integer of 1 to 3, when r1 and r2 are each 2 or greater, substituents in the parentheses are the same as or different from each other, and when Ar1 is and Ar2 is represented by the following Chemical Formula 4-1, L1 is direct bond, in Chemical Formula 4-1, R41 is hydrogen; deuterium; 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 heterocyclic group, r41 is an integer of 1 to 8, and when r41 is 2 or greater, substituent in the parentheses are the same as or different from each other, and the following compounds are excluded:
  2. The heterocyclic compound of Claim 1, wherein Chemical Formula 4 is represented by any one of the following Chemical Formulae 4-1 to 4-5: in Chemical Formulae 4-1 to 4-5, Y is O; S; NR' or CR'R", R', R" and R41 to R45 are each independently hydrogen; deuterium; 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 heterocyclic group, r41 is an integer of 1 to 8, r42 and r43 are each an integer of 1 to 6, r44 is an integer of 1 to 5, r45 is an integer of 1 to 4, and when r41 to r45 are each 2 or greater, substituents in the parentheses are the same as or different from each other.
  3. The heterocyclic compound of Claim 1, wherein L1 and L2 are each independently a direct bond; or a phenylene group.
  4. The heterocyclic compound of Claim 1, wherein the heterocyclic compound is represented by any one of the following compounds:
  5. An organic light emitting device comprising: a first electrode; a second electrode; and an organic material layer (300) provided between the first electrode and the second electrode, wherein the organic material layer (300) includes one or more types of the heterocyclic compound of any one of Claims 1 to 4.
  6. The organic light emitting device of Claim 5, wherein the organic material layer (300) includes a light emitting layer (303), and the light emitting layer (303) includes one or more types of the heterocyclic compound.
  7. The organic light emitting device of Claim 6, wherein the light emitting layer (303) includes a host, and the host includes one or more types of the heterocyclic compound.
  8. The organic light emitting device of Claim 6, wherein the light emitting layer (303) includes a host, and the host further includes a compound of the following Chemical Formula 5: in Chemical Formula 5, R21 and R22 are each a substituted or unsubstituted C6 to C60 aryl group.
  9. The organic light emitting device of Claim 5, further comprising one layer selected from the group consisting of a light emitting layer, a hole injection layer (301), a hole transfer layer (302), an electron injection layer (306), an electron transfer layer (305), an electron blocking layer and a hole blocking layer (304).

Description

[Technical Field] The present specification relates to a heterocyclic compound, and an organic light emitting device including the same. This application claims priority to and the benefits of Korean Patent Application No. 10-2019-0119670, filed with the Korean Intellectual Property Office on September 27, 2019. [Background Art] An 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. Organic light emitting devices have been disclosed in KR 102 021 294 B1, EP 4 015 515 A1, EP 3 828 180 A1, EP 3 832 746 A1 and CN 104 650 029 A 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. [Disclosure] [Technical Problem] The present specification is directed to providing a heterocyclic compound, and an organic light emitting device including the same. [Technical Solution] The technical problem is solved by claim 1 relating to compounds of Chemical Formula 1-1 or 1-2, and by organic light emitting devices according to claim 5. One embodiment of the present specification provides a heterocyclic compound represented by the following Chemical Formula 1. In Chemical Formula 1, L1 and L2 are each independently a direct bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted divalent C2 to C60 heterocyclic group,Ar1 is a substituted or unsubstituted C2 to C60 heterocyclic group including N,Ar2 is -N(R106) (R107); or a substituted or unsubstituted C2 to C60 heterocyclic group,R1 and R2 are each independently hydrogen; deuterium; a halogen group; 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 heterocyclic group,R106 and R107 are each independently hydrogen; deuterium; a halogen group; an alkyl group; an alkenyl group; an alkoxy group; a cycloalkyl group; an aryl group; or a heterocyclic group,r1 and r2 are each an integer of 1 to 4, andwhen r1 and r2 are each 2 or greater, substituents in the parentheses are the same as or different from each other. Another embodiment of the present application provides an organic light emitting device including a first electrode; a second electrode provided opposite to the first electrode; and an organic material layer provided between the first electrode and the second electrode, wherein the organic material layer includes one or more types of the heterocyclic compound represented by Chemical Formula 1. [Advantageous Effects] A compound described in the present specification can be used as a material of an organic material layer of an organic light emitting device. The compound is capable of performing a role of a hole injection material, a hole transfer material, a light emitting material, an electron transfer material, an electron injection material or the like in the organic light emitting device. Particularly, the compound can be used as a light emitting layer material of an organic light emitting device. For example, the compound can be used alone as a light emitting material, or can be used as a host material of a light emitting layer. By Chemical Formula 1 having a structure in which naphthobenzofuran is disubstituted with an amine group or a heterocyclic group including nitrogen, the HOMO level is delocalized helping with electron and hole transfers. Accordingly, Chemical Formula 1 is readily used as a host, and effects of increasing efficiency and lifetime are obtained depending on the substituted position of the naphthobenzofuran. By introducing various substituents to the naphthobenzofuran of Chemical Formula 1, a hole transfer ability of the central structure increases, and the expanded conjugation structure can stabilize homo energy. This forms proper energy level and b