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JP-7856720-B2 - Compounds, materials for organic electroluminescent elements, organic electroluminescent elements, and electronic devices.

JP7856720B2JP 7856720 B2JP7856720 B2JP 7856720B2JP-7856720-B2

Inventors

  • 三谷 真人
  • 水谷 清香
  • 高橋 良多
  • 山田 啓太郎

Assignees

  • 出光興産株式会社

Dates

Publication Date
20260511
Application Date
20240925
Priority Date
20220713

Claims (10)

  1. An electron transport material compound represented by the following formula (1). [In formula (1), X1 is N, and X2 is CH. Ar 1 and Ar 2 are independent of each other. Unsubstituted phenyl group, Unsubstituted p-biphenyl group, Unsubstituted m-biphenyl group, Unsubstituted o-biphenyl group, Unsubstituted p-terphenyl-4-yl group, Unsubstituted p-terphenyl-3-yl group, Unsubstituted p-terphenyl-2-yl group, Unsubstituted m-terphenyl-4-yl group, Unsubstituted m-terphenyl-3-yl group, Unsubstituted m-terphenyl-2-yl group, Unsubstituted o-terphenyl-4-yl group, Unsubstituted o-terphenyl-3-yl group, Unsubstituted o-terphenyl-2-yl group, Unsubstituted 1-naphthyl group, Unsubstituted 2-naphthyl group, Unsubstituted phenanthryl group, 9,9-dimethylfluorenyl group, 9,9-diphenylfluorenyl group, It is an unsubstituted dibenzofuranyl group or an unsubstituted dibenzothiophenyl group. L1 and L2 are independent of each other. It is an unsubstituted arylene group having 6 to 18 ring-forming carbon atoms, or an unsubstituted divalent heterocyclic group having 5 to 18 ring-forming atoms. n1 is an integer between 0 and 4. If n1 is 0, then ( L1 ) n1 is a single associative chain. If there are multiple L1s , each of the L1s may be the same or different. n² is an integer between 0 and 4. If n² is 0, then ( L² ) n² is single-associative. If there are multiple L²s , each of the L²s may be the same or different. (L 3 ) n3 is , It is a substituted or unsubstituted phenylene group. R11 through R19 are hydrogen atoms. R21 and R22 do not bond to each other to form substituted or unsubstituted saturated or unsaturated rings. R21 and R22 are methyl groups.
  2. Ar 1 and Ar 2 are independent of each other. Unsubstituted phenyl group, Unsubstituted p-biphenyl group, Unsubstituted m-biphenyl group, Unsubstituted o-biphenyl group, Unsubstituted p-terphenyl-4-yl group, Unsubstituted p-terphenyl-3-yl group, Unsubstituted p-terphenyl-2-yl group, Unsubstituted m-terphenyl-4-yl group, Unsubstituted m-terphenyl-3-yl group, Unsubstituted m-terphenyl-2-yl group, Unsubstituted o-terphenyl-4-yl group, Unsubstituted o-terphenyl-3-yl group, Unsubstituted o-terphenyl-2-yl group, Unsubstituted 1-naphthyl group, The electron transport material compound according to claim 1 , wherein the compound is an unsubstituted 2-naphthyl group or an unsubstituted phenanthryl group.
  3. One of Ar 1 and Ar 2 is Unsubstituted phenyl group, Unsubstituted p-biphenyl group, Unsubstituted m-biphenyl group, Unsubstituted o-biphenyl group, Unsubstituted p-terphenyl-4-yl group, Unsubstituted p-terphenyl-3-yl group, Unsubstituted p-terphenyl-2-yl group, Unsubstituted m-terphenyl-4-yl group, Unsubstituted m-terphenyl-3-yl group, Unsubstituted m-terphenyl-2-yl group, Unsubstituted o-terphenyl-4-yl group, Unsubstituted o-terphenyl-3-yl group, Unsubstituted o-terphenyl-2-yl group, Unsubstituted 1-naphthyl group, An unsubstituted 2-naphthyl group, or an unsubstituted phenanthryl group, On the other hand, 9,9-dimethylfluorenyl group, 9,9-diphenylfluorenyl group, The electron transport material compound according to claim 1 , wherein the compound is an unsubstituted dibenzofuranyl group or an unsubstituted dibenzothiophenyl group.
  4. The electron transport material compound according to claim 1 , wherein the compound represented by formula (1) is the compound represented by the following formula (211). [In formula (211), Ar 1 , Ar 2 , L 1 , L 2 , n1, n2, and R 11 to R 19 are as defined in formula (1) above. R211 to R214 are each independently a hydrogen atom or a substituent R. Two or more adjacent atoms from R211 to R214 cannot bond to each other. The substituent R is Cyano group, Alkyl alkyl groups having 1 to 18 carbon atoms, Selected from the group consisting of aryl groups with 6 to 18 ring-forming carbon atoms and monovalent heterocyclic groups with 5 to 18 ring-forming atoms.
  5. The electron transport material compound according to claim 1, wherein ( L1 ) n1 and ( L2 ) n2 are each independently a single bond, an unsubstituted phenylene group, or an unsubstituted naphthylene group.
  6. The electron transport material compound according to claim 1, wherein Ar 1 and Ar 2 are each independently an unsubstituted phenyl group, an unsubstituted 1-naphthyl group, an unsubstituted 2-naphthyl group, an unsubstituted p-biphenyl group, an unsubstituted m -biphenyl group, or an unsubstituted o-biphenyl group.
  7. When we say "substituted or unsubstituted," the substituent is Alkyl alkyl groups having 1 to 18 carbon atoms, The electron transport material compound according to claim 1, wherein the group is selected from the group consisting of an aryl group having 6 to 18 ring-forming carbon atoms and a monovalent heterocyclic group having 5 to 18 ring-forming atoms.
  8. The anode, light-emitting layer, electron transport band, and cathode are included in this order. An organic electroluminescent element wherein the electron transport band contains the electron transport material compound described in claim 1 .
  9. The electron transport band has the first layer and the second layer in this order from the light-emitting layer side. The organic electroluminescent element according to claim 8 , wherein the first layer comprises the electron transport material compound.
  10. An electronic device comprising an organic electroluminescent element as described in claim 8 .

Description

This invention relates to novel compounds, materials for organic electroluminescent devices, organic electroluminescent devices, and electronic devices. When a voltage is applied to an organic electroluminescent element (hereinafter also referred to as an organic EL element), holes are injected from the anode and electrons from the cathode into the light-emitting layer. Then, in the light-emitting layer, the injected holes and electrons recombine to form excitons. Conventional organic EL (OLED) devices still lacked sufficient performance. While improvements to the materials used in OLED devices are gradually progressing to enhance performance, further performance improvements are still required. International Publication No. 2016/105141International Publication No. 2022/181157 This figure shows a schematic configuration of an organic EL element according to one aspect of the present invention. [Definition] In this specification, the term "hydrogen atom" includes isotopes with different numbers of neutrons, namely protium, deuterium, and tritium. In this specification, in chemical structural formulas, any bondable positions where symbols such as "R" or "D" (representing a deuterium atom) are not explicitly indicated shall be assumed to be bonded to hydrogen atoms, i.e., light hydrogen atoms, deuterium atoms, or tritium atoms. In this specification, the ring-forming carbon number refers to the number of carbon atoms among the atoms constituting the ring itself in a compound with a structure in which atoms are bonded in a ring (e.g., monocyclic compounds, fused ring compounds, crosslinked compounds, carbocyclic compounds, and heterocyclic compounds). If the ring is substituted by a substituent, the carbon atoms in the substituent are not included in the ring-forming carbon number. The same applies to the "ring-forming carbon number" described below unless otherwise specified. For example, a benzene ring has 6 ring-forming carbon atoms, a naphthalene ring has 10 ring-forming carbon atoms, a pyridine ring has 5 ring-forming carbon atoms, and a furan ring has 4 ring-forming carbon atoms. Also, for example, the ring-forming carbon number of a 9,9-diphenylfluorenyl group is 13, and the ring-forming carbon number of a 9,9'-spirobifluorenyl group is 25. Furthermore, when a benzene ring is substituted with an alkyl group, for example, the number of carbon atoms in the alkyl group is not included in the number of ring-forming carbon atoms of the benzene ring. Therefore, the number of ring-forming carbon atoms in a benzene ring substituted with an alkyl group is 6. Similarly, when a naphthalene ring is substituted with an alkyl group, for example, the number of carbon atoms in the alkyl group is not included in the number of ring-forming carbon atoms of the naphthalene ring. Therefore, the number of ring-forming carbon atoms in a naphthalene ring substituted with an alkyl group is 10. In this specification, the number of ring-forming atoms refers to the number of atoms that constitute the ring itself in compounds with a ring-bonded structure (e.g., monocyclic compounds, fused rings, and ring assemblies) (e.g., monocyclic compounds, fused ring compounds, bridged compounds, carbocyclic compounds, and heterocyclic compounds). Atoms that do not constitute a ring (e.g., hydrogen atoms that terminate the bonds of ring-forming atoms) and atoms included in substituents when the ring is substituted by substituents are not included in the number of ring-forming atoms. The same applies to "number of ring-forming atoms" as described below unless otherwise specified. For example, the number of ring-forming atoms in a pyridine ring is 6, the number of ring-forming atoms in a quinazoline ring is 10, and the number of ring-forming atoms in a furan ring is 5. For example, the number of hydrogen atoms bonded to a pyridine ring, or the number of atoms constituting substituents, are not included in the number of pyridine ring-forming atoms. Therefore, the number of ring-forming atoms in a pyridine ring to which hydrogen atoms or substituents are bonded is 6. Furthermore, for example, hydrogen atoms bonded to the carbon atom of the quinazoline ring, or atoms constituting substituents, are not included in the number of ring-forming atoms of the quinazoline ring. Therefore, the number of ring-forming atoms of a quinazoline ring to which hydrogen atoms or substituents are bonded is 10. In this specification, the expression "substituted or unsubstituted ZZ group with carbon numbers XX to YY" refers to the number of carbon atoms in the unsubstituted ZZ group, and does not include the number of carbon atoms of substituents in the case of substitution. Here, "YY" is greater than "XX," where "XX" is an integer of 1 or more, and "YY" is an integer of 2 or more. In this specification, the expression "ZZ group with substituted or unsubstituted atoms of XX to YY" refers to the number of atoms when the ZZ group is unsubstituted, and does not include the