Organic electric light emitting element, material for said element, and light emitting device, display device, and illumination device employing said element

Patent metadata

Field	Value
Publication number	US-12404264-B2
Application number	US-201916662143-A
Country	US
Kind code	B2
Filing date	Oct 24, 2019
Priority date	Aug 11, 2011
Publication date	Sep 2, 2025
Grant date	Sep 2, 2025

Abstract

An organic electroluminescent element including a substrate, a pair of electrodes including an anode and a cathode, disposed on the substrate, and at least one organic layer including a light emitting layer, disposed between the electrodes, in which the organic layer includes a compound represented by the following general formula, has high luminous efficiency, excellent blue color purity, and a small change in the chromaticity due to deterioration by driving (Cy represents a fused aromatic ring structure having the number of constituent rings of 3 or more, and has Dn 1 and Ac 1 as different constituent rings, and each of the constituent rings are all hydrocarbon rings. Dn 1 represents NR 11 , an O atom, or an S atom. Ac 1 represents an electron absorbing substituent, an aryl group having an electron absorbing substituent, or an electron deficient heteroaryl group. The ring Z 1 represents an arylene group or a heteroarylene group. L 1 , L 2 and L 3 represent specific linking groups. u1 represents 0 or 1, and in the case where u1 is 1, the ring thus formed is not an aromatic ring. n1 and q1 represent 0 or 1, and in the case where any one of n1 and q1 is 0 and n1 or q1 is 1, the rings thus formed are not all aromatic rings. When Ac 1 is a pyridine ring, at least one of n1 and q1 is 1.)

First claim

We claim:

1. A material for an organic electroluminescent element, which is represented by the following general formula (1):

wherein
Dn 1 represents NR 11 , an O atom, or an S atom; R 11 represents a substituent, and R 11 may be bonded to Cy to form a ring other than an aromatic ring;
Ac 1 represents an electron absorbing substituent, an aryl group having a substituent selected from the group consisting of a halogen atom, a cyano group, and a trifluoromethyl group, or an electron deficient heteroaryl group, and Ac 1 may further have a substituent;
wherein the Cy is represented by pyrene which may have a substituent, has any one of the Dn 1 and the Ac 1 at the 1- or 3-position of the pyrene, and has the other of the Dn 1 and the Ac 1 at the 6- or 8-position of the pyrene, in the general formula (1);
Ring Z 1 represents an arylene group or a heteroarylene group, A 11 represents a carbon atom constituting the ring Z 1 , and A 12 represents a carbon atom or a nitrogen atom constituting the ring Z 1 ;
L 1 , L 2 and L 3 each independently represent an oxygen atom, a sulfur atom, CR 12 R 13 , or SiR 14 R 15 , and R 12 , R 13 , R 14 and R 15 each independently represent a hydrogen atom or a substituent;
wherein at least one of L 1 , L 2 , and L 3 is not sulfur;
u1 represents 1;
m1 represents 0 or 1, and when m1 is 0, Cy and ring Z 1 are directly bonded to each other;
n1 and q1 represent 0 or 1, and in the case where any one of n1 and q1 is 0 and n1 or q1 is 1, the rings formed by Cy, Ac 1 and L 2 or L 3 are not all aromatic rings,
wherein when Ac 1 is a pyridine ring, at least one of n1 and q1 is 1;
wherein at least one of the conditions (i) and (ii) is true:
(i) L 2 and L 3 are not sulfur; and
(ii) Ac 1 is not an aryl group substituted with fluorine.

2. An organic electroluminescent element comprising:
a substrate;
a pair of electrodes including an anode and a cathode, disposed on the substrate; and

at least one organic layer including a light emitting layer, disposed between the electrodes, wherein the organic layer includes the material according to claim 1 .

3. The organic electroluminescent element according to claim 2 , wherein the compound represented by the general formula (1) is a light emitting material.

4. A device using the organic electroluminescent element according to claim 2 , wherein the device is selected from the group consisting of a light emitting device, a display device, or an illumination device.

5. The material according to claim 1 , wherein Ac 1 is not an aryl group substituted with fluorine.

6. A material for an organic electroluminescent element, which is represented by any one of the following general formulae (2) to (5):

wherein Dn 2 represents an N atom, an O atom, or an S atom, and in the case where Dn 2 represents an O atom or an S atom, the sum of u21 and t24 is 0 or 1, wherein in the case where Dn 2 represents an N atom, at least one of u21 and t24 represents 0, or wherein in the case where Dn 2 represents an O atom or an S atom, u21 and t24 are both 0, Dn 2 further has a substituent;
Ac 2 represents an electron absorbing substituent, an aryl group having an electron absorbing substituent, or an electron deficient heteroaryl group, and Ac 2 may further have a substituent;
Ring Z 21 and ring Z 24 each independently represents an arylene group or a heteroarylene group, A 21 represents a carbon atom constituting the ring Z 21 , A 22 represents a carbon atom or a nitrogen atom constituting the ring Z 21 , A 27 represents a carbon atom constituting the ring Z 24 , and A 28 represents a carbon atom or a nitrogen atom constituting the ring Z 24 ;
R 103 , R 104 , R 108 and R 109 each independently represent a hydrogen atom or a substituent;
L 21 , L 22 , L 23 and L 24 each independently represent an oxygen atom, a sulfur atom, CR 22 R 23 , or SiR 24 R 25 , and R 22 , R 23 , R 24 and R 25 each independently represent a hydrogen atom or substituent;
wherein at least one of L 21 , L 22 , L 23 , and L 24 is not sulfur;
u21 represents 0 or 1, and in the case where u21 is 0, the #positions of the pyrene ring and Dn 2 are not bonded to each other;
t24 represents 0 or 1, in the case where t24 is 0, the #positions of the pyrene ring and Dn 2 are not bonded to each other;
m21 represents 0 or 1, and when m21 is 0 and u21 is 1, #positions of pyrene ring and ring Z 21 are directly bonded to each other;
s24 represents 0 or 1, and when s24 is 0 and u24 is 1, the #positions of pyrene ring and ring Z 24 are directly bonded to each other;
n22 and q23 represent 0 or 1, in the case where any one of n22 and q23 is 0 and n22 or q23 is 1, the rings formed by the pyrene ring, Ac 2 and L 22 or L 23 are not all aromatic rings; wherein the case where n22 or q23 is 0, the * positions of the pyrene ring and Ac 2 are not bonded to each other wherein when Ac 2 is a pyridine ring, at least one of n22 and q23 is 1;

wherein Dn 3 represents an N atom, an O atom, or an S atom, and in the case where Dn 3 represents an O atom or an S atom, the sum of u31 and t34 is 0 or 1; where when Dn 3 represents an N atom, at least one of u31 and t34 represents 0, and when in the case where u31 and t34 are each 0, Dn 3 further has two substituents, or when in the case where one of u31 and t34 is 1, then Dn 3 further has one substituent; or when in the case where Dn 3 represents an O atom or an S atom and u31 and t34 are both 0, Dn 3 further has a substituent;
Ac 3 represents an electron absorbing substituent, an aryl group having an electron absorbing substituent, or an electron deficient heteroaryl group, and Ac 3 may further have a substituent;
Ring Z 31 and the ring Z 34 each independently represent an arylene group or a heteroarylene group, A 31 represents a carbon atom constituting ring Z 31 , and A 32 represents a carbon atom or a nitrogen atom constituting ring Z 31 , A 37 represents a carbon atom constituting ring Z 34 , and A 38 represents a carbon atom or a nitrogen atom constituting ring Z 34 ;
R 113 , R 114 , R 115 and R 116 each independently represent a hydrogen atom or a substituent;
L 31 , L 32 , L 33 and L 34 each independently represent an oxygen atom, a sulfur atom, CR 32 R 33 , or SiR 34 R 35 , and R 32 , R 33 , R 34 and R 35 each independently represent hydrogen or a substituent;
u31 represents 1;
t34 represents 0 or 1, and in the case where t34 is 0, the #positions of the pyrene ring and Dn 3 are not bonded to each other;
m31 represents 0 or 1, and when m31 is 0 and u31 is 1, the #positions of the pyrene ring and ring Z 31 are directly bonded to each other;
m34 represents 0 or 1 and when m34 is 0 and t34 is 1, the #positions of the pyrene ring and ring Z 34 are directly bonded to each other;
n32 and q33 represent 0 or 1, and in the case where any one of n32 and q33 is 0 and n32 or q33 is 1, the rings formed by the pyrene ring, Ac 3 and L 32 or L 33 are not all aromatic rings; where when n32 or q33 is 0, the * positions of the pyrene ring and Ac 3 are not bonded to each other, wherein when Ac 3 is a pyridine ring, at least one of n32 and q33 is 1;

Assignees

• Udc Ireland Ltd

Inventors

• Takaku Koji
• Kitamura Tetsu
• Sotoyama Wataru
• Yonekuta Yasunori
• Watanabe Toru
• Ise Toshihiro
• Takada Saki

Classifications

• H10K50/181

  Electron blocking layers · CPC title

• H10K50/171

  Electron injection layers · CPC title

• H10K50/18

  Carrier blocking layers · CPC title

• H10K50/17

  Carrier injection layers · CPC title

• H10K50/16

  Electron transporting layers · CPC title