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US 11,871,656 B2Granted
Organic electroluminescence device and monoamine compound for organic electroluminescence device
AssigneeSamsung Display Co., Ltd.
InventorsHideo Miyake, Masatsugu Ueno, Xiulan Jin, Ichinori Takada, Takuya Uno, Hiroaki Itoi
Life of this patent
Estimating the term…
Abstract
An organic electroluminescence device includes a first electrode, a hole transport region on the first electrode, an emission layer on the hole transport region, an electron transport region on the emission layer, and a second electrode on the electron transport region. The hole transport region includes a monoamine compound represented by the following Formula 1:
Claims18
An organic electroluminescence device, comprising:
- a first electrode;
- a hole transport region on the first electrode;
- an emission layer on the hole transport region;
- an electron transport region on the emission layer;
- and
- a second electrode on the electron transport region,
- wherein the hole transport region includes a monoamine compound represented by at least one of the following Formulae 2 to 8:
- wherein in Formula 2 to 8,
- Ar1 and Ar2 are each independently a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, provided that when any one of Ar1 and Ar2 is 3-dibenzofuranyl, the other one of Ar1 and Ar2 is not 9-phenanthryl,
- L is a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms,
- R1 is a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms,
- R2 is a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms,
- a is an integer of 0 to 3,
- m is an integer of 0 to 1, and
- n is an integer of 0 to 6,
- wherein in Formula 3,
- i) when one of Ar1 and Ar2 is a naphthalene group or a phenyl group substituted with a naphthalene group and the other one of Ar1 and Ar2 is a substituted or unsubstituted aryl group,
- the naphthalene group in the one of Ar1 and Ar2 is unsubstituted, or
- the substituted or unsubstituted aryl group of the other one of Ar1 and Ar2 is a substituted or unsubstituted aryl group having 7 to 30 ring carbon atoms, and
- ii) L is a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms,
- wherein in Formula 4, a is an integer of 1 to 3,
- wherein in Formula 6,
- i) Ar1 and Ar2 are not dimethylfluorenyl groups,
- ii) when any one of Ar1 and Ar2 is a p-biphenyl group and the other one of Ar1 and Ar2 includes an aryl substituent, the number of ring carbon atoms in the aryl substituent is 13 to 30,
- iii) L is a phenylene group, a is an integer of 1 or more and 3 or less, and when L includes an m-phenylene group, Ar1 and Ar2 are not an unsubstituted or alkyl-substituted phenyl group, or an unsubstituted p-biphenyl group, and
- vi) when Ar1 and Ar2 are each a heteroaryl group comprising S, or one of Ar1 or Ar2 is a heteroaryl group comprising S, and an other one of Ar1 or Ar2 is a heteroaryl group comprising O, the heteroaryl group comprising S is a substituted or unsubstituted dibenzothiophene group, and the heteroaryl group comprising O is a substituted or unsubstituted dibenzofuran group, and
- wherein in Formula 7 and Formula 8,
- i) Ar1 and Ar2 are not an unsubstituted p-biphenyl group or an unsubstituted p-terphenyl group,
- ii) when Ar1 and Ar2 are a fluorene group or a fluorene derivative, Ar1 and Ar2 are substituents represented by Formula 7a;
- wherein in Formula 7a,
- R3 is a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms,
- R4 and R5 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, and/or combine with each other to form a ring,
- is an integer of 0 or more and 3 or less,
- p is an integer of 0 or more and 4 or less,
- iii) L is a substituted or unsubstituted phenylene group, and
- vi) when one of Ar1 and Ar2 is an unsubstituted 2-dibenzofuran group, an unsubstituted 2-dibenzothiophene group, an unsubstituted 3-dibenzofuran group, or an unsubstituted 3-dibenzothiophene group, the other one of Ar1 and Ar2 is a substituted or unsubstituted phenylnaphthyl group, a substituted or unsubstituted dibenzofuran group, or a substituted or unsubstituted dibenzothiophene group.
33 more elements
A monoamine compound represented by at least one of the following Formulae 2 to 8:
- wherein in Formula 2 to 8,
- Ar1 and Ar2 are each independently a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, provided that when any one of Ar1 and Ar2 is 3-dibenzofuranyl, the other one of Ar1 and Ar2 is not 9-phenanthryl,
- L is a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms,
- R1 is a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms,
- R2 is a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms,
- a is an integer of 0 to 3,
- m is an integer of 0 to 1, and
- n is an integer of 0 to 6,
- wherein in Formula 3, when one of Ar1 and Ar2 is a naphthalene group or a phenyl group substituted with a naphthalene group and the other one of Ar1 and Ar2 is a substituted or unsubstituted aryl group,
- the naphthalene group in the one of Ar1 and Ar2 is unsubstituted, or
- the substituted or unsubstituted aryl group of the one of Ar1 and Ar2 is a substituted or unsubstituted aryl group having 7 to 30 ring carbon atoms,
- wherein in Formula 4, a is an integer of 1 to 3,
- wherein in Formula 6,
- i) Ar1 and Ar2 are not dimethylfluorenyl groups,
- ii) when any one of Ar1 and Ar2 is a p-biphenyl group and the other one of Ar1 and Ar2 includes an aryl substituent, the number of ring carbon atoms in the aryl substituent is 13 to 30,
- iii) L is a phenylene group, a is an integer of 1 or more and 3 or less, and when L includes an m-phenylene group, Ar1 and Ar2 are not an unsubstituted or alkyl-substituted phenyl group, or an unsubstituted p-biphenyl group, and
- vi) when Ar1 and Ar2 are each a heteroaryl group comprising S, or one of Ar1 or Ar2 is a heteroaryl group comprising S, and an other one of Ar1 or Ar2 is a heteroaryl group comprising O, the heteroaryl group comprising S is a substituted or unsubstituted dibenzothiophene group, and the heteroaryl group comprising O is a substituted or unsubstituted dibenzofuran group, and
- wherein in Formula 7 and Formula 8,
- i) Ar1 and Ar2 are not an unsubstituted p-biphenyl group or an unsubstituted p-terphenyl group,
- ii) when Ar1 and Ar2 are a fluorene group or a fluorene derivative, Ar1 and Ar2 are substituents represented by Formula 7a;
- wherein in Formula 7a,
- R3 is a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms,
- R4 and R5 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or may combine with each other to form a ring,
- is an integer of 0 or more and 3 or less,
- p is an integer of 0 or more and 4 or less,
- iii) L is a substituted or unsubstituted phenylene group, and
- vi) when one of Ar1 and Ar2 is an unsubstituted 2-dibenzofuran group, an unsubstituted 2-dibenzothiophene group, an unsubstituted 3-dibenzofuran group, or an unsubstituted 3-dibenzothiophene group, the other one of Ar1 and Ar2 is a substituted or unsubstituted phenylnaphthyl group, a substituted or unsubstituted dibenzofuran group, or a substituted or unsubstituted dibenzothiophene group.
24 more elements
Dependencies are inferred from the claim text.