Silsesquioxane compound, organic light emitting element, display apparatus, image information processing apparatus, and image forming apparatus

Patent metadata

Field	Value
Publication number	US-2016118607-A1
Application number	US-201414779185-A
Country	US
Kind code	A1
Filing date	Mar 25, 2014
Priority date	Apr 3, 2013
Publication date	Apr 28, 2016
Grant date	—

Abstract

Provided is an organic light emitting element having high light emitting efficiency. The organic light emitting element includes: an anode; a cathode; an emission layer placed between the anode and the cathode; and a hole transport layer formed between the anode and the emission layer, in which the hole transport layer contains a siloxane compound and a compound having a tertiary arylamine structure; and number of SP 2 carbon atoms in the hole transport layer is ten times or less number of silicon atoms in the hole transport layer.

First claim

1 . An organic light emitting element comprising:
an anode; a cathode; an emission layer placed between the anode and the cathode; and a hole transport layer formed between the anode and the emission layer, wherein the hole transport layer comprises a siloxane compound and a compound having a tertiary arylamine structure; and wherein a number of SP 2 carbon atoms in the hole transport layer is ten times or less a number of silicon atoms in the hole transport layer.

2 . The organic light emitting element according to claim 1 , wherein the number of the SP 2 carbon atoms in the hole transport layer is 6.67 times or less the number of the silicon atoms in the hole transport layer.

3 . The organic light emitting element according to claim 1 , wherein the siloxane compound comprises a silsesquioxane compound represented by any one of the following general formulae [1] to [3]:

in the formulae [1] to [3], R 1 represents an alkyl group having 1 or more and 8 or less carbon atoms, and multiple R 1 's represented in each of the formulae [1] to [3] may be identical to or different from each other;
in the formula [1], Z 1 represents a monovalent alkyl group having 1 to 8 carbon atoms, a unit represented by the following general formula [4A], or an aromatic amino group selected from the following general formulae [5] to [9]:

in the formula [4A], Ar 1a to Ar 3a each represent a substituted or unsubstituted aryl group, * represents a bonding hand with a silsesquioxane skeleton, and m and n each represent 0 or 1, provided that n represents 0 when m represents 0;

in the formula [5], A 1 to A 3 each represent a bonding hand with a silsesquioxane skeleton or a unit represented by the following general formula [10A];
in the formula [6], A 4 , A 5 , A 7 , and A 8 each represent a bonding hand with a silsesquioxane skeleton or a unit represented by the following general formula [10A], and A 6 represents a bonding hand with a silsesquioxane skeleton or a unit represented by any one of the following general formulae [10B] to [10D];
in the formula [7], A 9 to A 14 each represent a bonding hand with a silsesquioxane skeleton or a unit represented by the following general formula [10A], and A 15 represents a bonding hand with a silsesquioxane skeleton or a unit represented by any one of the following general formulae [10E] to [10G];
in the formula [8], A 16 , A 17 , A 19 , A 21 , and A 22 each represent a bonding hand with a silsesquioxane skeleton or a unit represented by the following general formula [10A], and A 18 and A 20 each represent a bonding hand with a silsesquioxane skeleton or a unit represented by any one of the following general formulae [10B] to [10D]; and
in the formula [9], A 23 , A 24 , A 27 , A 28 , A 30 , and A 31 each represent a bonding hand with a silsesquioxane skeleton or a unit represented by the following general formula [10A], and A 25 , A 26 , and A 29 each represent a bonding hand with a silsesquioxane skeleton or a unit represented by any one of the following general formulae [10B] to [10D]:

in the formulae [10A] to [10G], Ar 1 to Ar 3 each represent an alkyl group having 1 to 8 carbon atoms, a phenoxy group that may have an alkyl group having 1 or more and 8 or less carbon atoms, or an aryl group that may have an alkoxy group,  represents a bonding hand with an N atom, and m and n each represent 0 or 1, provided that n represents 0 when m represents 0;
in the formula [2], Z 2 represents a divalent alkyl group having 1 to 8 carbon atoms, a unit represented by any one of the following general formulae [4B] to [4D], or an aromatic amino group selected from the following general formulae [5] to [9]:

in the formulae [4B] to [4D], Ar 1a to Ar 3a each represent an alkyl group having 1 to 8 carbon atoms, a phenoxy group that may have an alkyl group having 1 or more and 8 or less carbon atoms, or an aryl group that may have an alkoxy group, * represents a bonding hand with a silsesquioxane skeleton, and m and n each represent 0 or 1, provided that n represents 0 when m represents 0;

in the formula [5], A 1 to A 3 each represent a bonding hand with a silsesquioxane skeleton or a unit represented by the following general formula [10A];
in the formula [6], A 4 , A 5 , A 7 , and A 8 each represent a bonding hand with a silsesquioxane skeleton or a unit represented by the following general formula [10A], and A 6 represents a unit represented by any one of the following general formulae [10B] to [10D];
in the formula [7], A 9 to A 14 each represent a bonding hand with a silsesquioxane skeleton or a unit represented by the following general formula [10A], and A 15 represents a unit represented by any one of the following general formulae [10E] to [10G];
in the formula [8], A 16 , A 17 , A 19 , A 21 , and A 22 each represent a bonding hand with a silsesquioxane skeleton or a unit represented by the following general formula [10A], and A 18 and A 20 each represent a unit represented by any one of the following general formulae [10B] to [10D]; and
in the formula [9], A 23 , A 24 , A 27 , A 28 , A 30 , and A 31 each represent a bonding hand with a silsesquioxane skeleton or a unit represented by the following general formula [10A], and A 25 , A 26 , and A 29 each represent a unit represented by any one of the following general formulae [10B] to [10D]:

in the formulae [10A] to [10G], Ar 1 to Ar 3 each represent a substituted or unsubstituted aryl group,  represents a bonding hand with an N atom, and m and n each represent 0 or 1, provided that n represents 0 when m represents 0; and
in the formula [3], Z 3 represents a trivalent alkyl group having 1 to 8 carbon atoms, a unit represented by any one of the following general formulae [4E] to [4G], or an aromatic amino group selected from the following general formulae [5] to [9]:

in the formulae [4E] to [4G], Ar 1a to Ar 3a each represent a substituted or unsubstituted aryl group, * represents a bonding hand with a silsesquioxane skeleton, and m and n each represent 0 or 1, provided that n represents 0 when m represents 0;

in the formula [5], A 1 to A 3 each represent a bonding hand with a silsesquioxane skeleton or a unit represented by the following general formula [10A];
in the formula [6], A 4 , A 5 , A 7 , and A 8 each represent a bonding hand with a silsesquioxane skeleton or a unit represented by the following general formula [10A], and A 6 represents a unit represented by any one of the following general formulae [10B] to [10D];
in the formula [7], A 9 to A 14 each represent a bonding hand with a silsesquioxane skeleton or a unit represented by the following general formula [10A], and A 15 represents a unit represented by any one of the following general formulae [10E] to [10G

Assignees

• Canon Kk

Inventors

• Nishide Yosuke
• Yamada Naoki
• Kamatani Jun
• Ishii Ryuji
• Kajimoto Norifumi
• Ito Takayuki
• Mizuno Nobutaka
• Ishige Koichi
• Saitoh Akihito

Classifications

• G03G15/04036

  Details of illuminating systems, e.g. lamps, reflectors (lamp housings for copying cameras, reflex exposure lighting G03B27/542) · CPC title

• G06T1/00

  General purpose image data processing · CPC title

• H05B33/22

  characterised by the chemical or physical composition or the arrangement of auxiliary dielectric or reflective layers · CPC title

• H05B45/60

  Circuit arrangements for operating LEDs comprising organic material, e.g. for operating organic light-emitting diodes [OLED] or polymer light-emitting diodes [PLED] · CPC title

• H10K85/40

  Organosilicon compounds, e.g. TIPS pentacene · CPC title