Aromatic amine derivative and organic electroluminescent devices containing the same

Patent metadata

Field	Value
Publication number	US-11937499-B2
Application number	US-202017000576-A
Country	US
Kind code	B2
Filing date	Aug 24, 2020
Priority date	Aug 26, 2019
Publication date	Mar 19, 2024
Grant date	Mar 19, 2024

Abstract

Disclosed are an aromatic amine derivative and an organic electroluminescent device including the same. A fluorenyl/silafluorenyl group having an ortho-substituted group is introduced into the structure of the aromatic amine derivative. The aromatic amine derivative may be used as a light-emitting material in a light-emitting layer of an organic electroluminescent device. These novel compounds can provide better device performance.

First claim

What is claimed is:

1. A compound having a structure represented by one of Formula 5 to Formula 6:

in Formula 5 to Formula 6,
R 1 to R 5 and R 7 to R 11 are each independently selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted arylalkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, and combinations thereof;
R is selected from the group consisting of: substituted or unsubstituted aryl having 6 to 30 ring carbon atoms and substituted or unsubstituted heteroaryl having 3 to 30 ring atoms; and when R is selected from the aryl, R is not substituted or unsubstituted naphthyl;
the moiety

 comprises only one fluorene ring structure, azafluorene ring structure, spirobifluorene ring structure, or azaspirobifluorene ring structure;
X is C or Si;
L is selected from a single bond, substituted or unsubstituted arylene having 6 to 60 carbon atoms, or substituted or unsubstituted heteroarylene having 3 to 60 carbon atoms;
X 5 to X 8 are each independently selected from CR′ or N, and two adjacent C are present in X 1 to X 4 , wherein one of the two adjacent C is joined to L, and the other one of the two adjacent C is joined to R″; and the other two of X 1 to X 4 are each independently selected from CR′ or N;
R a , R b , and R′ are each independently selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted arylalkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a nitrile group, an isonitrile group, a thiol group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;
substituents R a and R b can be optionally joined to form a ring, and two adjacent substituents R′ can be optionally joined to form a ring; and
R″ is selected from halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, or substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms.

2. The compound of claim 1 , wherein in Formula 5 to Formula 6, each L is joined to X 2 , or each L is joined to X 3 .

3. The compound of claim 1 , wherein L is independently selected from a single bond, substituted or unsubstituted arylene having 6 to 12 carbon atoms, or substituted or unsubstituted heteroarylene having 3 to 12 carbon atoms.

4. The compound of claim 1 , wherein R′ is each independently selected from hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 6 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 10 ring carbon atoms, substituted or unsubstituted aryl having 6 to 12 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 12 carbon atoms, a nitrile group, or combinations thereof.

5. The compound of claim 1 , wherein R a and R b are each independently selected from substituted or unsubstituted alkyl having 1 to 6 carbon atoms or substituted or unsubstituted cycloalkyl having 3 to 10 ring carbon atoms, and R a and R b are not joined to form a ring.

6. The compound of claim 1 , wherein R has a structure represented by Formula 17:

in Formula 17, * represents a position where R is joined to N shown in Formula 5 or 6;
wherein the ring Ar 3 is aryl having 6 to 30 ring carbon atoms or heteroaryl having 3 to 30 ring atoms; and when the ring Ar 3 is aryl, the ring Ar 3 is not a naphthalene ring structure;
wherein R e represents mono-substitution, multi-substitution, or non-substitution; and
R e is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted arylalkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a nitrile group, an isonitrile group, a thiol group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof.

7. The compound of claim 1 , wherein R has a structure represented by Formula 14:

in Formula 14, * represents a position where R is joined to N shown in Formula 5 or 6;
wherein the ring Ar 3 is aryl having 6 to 30 ring carbon atoms or heteroaryl having 3 to 30 ring atoms; and when the ring Ar 3 is aryl, the ring Ar 3 is not a naphthalene ring structure;
R c represents ortho-substitution of the position where R is joined to N shown in Formula 5 or 6, and R d represents mono-substitution, multi-substitution, or non-substitution;
wherein R d is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted arylalkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubst

Assignees

• Beijing Summer Sprout Tech Co Ltd

Inventors

• Zhao Chunliang
• Wang Zheng
• Ye Dan
• Zhang Shaobo
• Li Hongbo
• Bi Xin
• Tian Xuechao
• Kwong Chi Yuen Raymond
• Xia Chuanjun

Classifications

• H10K85/633 Primary

  comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom · CPC title

• C07C211/61 Primary

  with at least one of the condensed ring systems formed by three or more rings · CPC title

• C07C255/58

  containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the carbon skeleton · CPC title

• C09K11/06 Primary

  containing organic luminescent materials · CPC title

• C09K2211/1007

  Non-condensed systems · CPC title