IP Library Granted Patent US 10,505,116
Granted Patent B2
US 10,505,116 · App. 13/812,785 · Granted Dec 10, 2019

Organic electroluminescent element and compound

Inventors: Kousuke Watanabe (Kanagawa, JP); Wataru Sotoyama (Kanagawa, JP)
Assignee: UDC IRELAND LIMITED
H01L51/0052C07D215/04C07D307/91C07D333/76C09B57/00C09K11/06H01L51/0074H01L51/5016H01L51/5048H05B33/14C09K2211/1007C09K2211/1011C09K2211/1029C09K2211/1044C09K2211/1059C09K2211/1088C09K2211/1092H01L51/0054H01L51/0072H01L51/0073H01L51/0085
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Quick Facts
Patent No.
US 10,505,116
App. No.
13/812,785
Granted
Dec 10, 2019
Kind
B2
Abstract

[Disclosed is] a high-efficiency and durable organic electroluminescent element having a low drive voltage, being an organic electroluminescent element having on a substrate a pair of electrodes comprising an anode and a cathode and at least one organic layer including a light-emitting layer between these electrodes, with this organic electroluminescent element containing a specific compound having a dibenzothiophene or dibenzofuran structure and a phenanthrene structure in at least one layer out of the aforementioned at least one organic layer. [Also disclosed is] this specific compound.

Claims (27)

1. An organic electroluminescent element having on a substrate a pair of electrodes comprising an anode and a cathode and at least one organic layer including a light-emitting layer between these electrodes, wherein at least one layer out of said at least one organic layer contains at least one type of compound expressed by General Formula 1 below:

wherein X represents an oxygen atom or a sulfur atom, R 111 to R 126 represent each independently a hydrogen atom or a substituent, and Ar 111 is represented by one of General Formulae (1-3) to (1-5) below:

wherein each occurrence of R 411 independently represents hydrogen or a substituent, with the proviso that two or more of the substituents expressed by R 411 cannot together form a condensed aromatic ring, and

each occurrence of n411 independently represents an integer from 0 to 4.

2. The organic electroluminescent element according to claim 1 , wherein the compound expressed by General Formula 1 above is a compound expressed by General Formula 3 below:

wherein, X represents an Oxygen atom or a sulfur atom, R 111 to R 126 represent each independently a hydrogen atom or a substituent, R 121 and R 122 do not form a condensed aromatic ring, R 127 and R128 represent each independently a substituent, n 311 and n 312 represent each independently 1 or 2, n 321 and n 322 represent each independently an integer from 0 to 4, and Ar 311 is represented by one of General Formula (1-1) to (1-3) below:

wherein each occurrence of R 411 independently represents hydrogen or a substituent, and each occurrence of n411 independently represents an integer from 0 to 4.

3. The organic electroluminescent element according to claim 1 , wherein said light-emitting layer contains a compound expressed by General Formula 1 above.

4. The organic electroluminescent element according to claim 1 , wherein said light-emitting layer contains an iridium complex.

5. The organic electroluminescent element according to claim 1 , wherein said light-emitting layer contains an iridium complex expressed by General Formula T-1below:

wherein, each of R T3 ′,R T3 , R T4 , R T5 , and R T6 independently represents a hydrogen atom or a substituent;

any adjacent two of R T3 , R T4 , R T5 , and R T6 , may bind together to form a condensed four- to seven-member ring, said condensed four- to seven-member ring is a cycloalkyl, an aryl, or a heteroaryl, and said condensed four- to seven-member ring may further have a substituent;

R T3 ′ and R T6 may form a ring by being linked by a linking group selected from among —C(R T ) 2 —C(R T ) 2 —, —CR T ═CR T —, —C(R T ) 2 —, —O—, —NR T —, —O —C(R T ) 2 —, —NR T —C(R T ) 2 —, and —N═CR T —, and each occurrence of R T independently represents a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group; an aryl group, or a heteroaryl group, and may further have a substituent;

the ring Q is a five- or six-member aromatic heterocycle or condensed aromatic heterocycle including at least one nitrogen; and

(X—Y) represents an auxiliary ligand, m is an integer of 1 to 3, n is an integer of 0 to 2, and m+n=3.

6. The organic electroluminescent element according claim 1 , wherein there is an electron transport layer between said light-emitting layer and said cathode, there is an intermediate layer between this electron transport layer and said light-emitting layer, and this intermediate layer contains a compound expressed by General Formula 1 above.

7. A compound expressed by General Formula 3:

X represents an oxygen atom or a sulfur atom, R 111 to R 126 represent each independently a hydrogen atom or a substituent, R 121 and R 122 do not form a condensed aromatic ring, R 127 and R 128 represent each independently a substituent, n 311 and n 312 represent each independently 1 or 2, n 321 and n 322 represent each independently an integer from 0 to 4, and Ar 311 is represented by or one of General Formula (1-1) to (1-3) below:

wherein each occurrence of R 411 independently represents hydrogen or a substituent, with the proviso that two or more of the substituents expressed by R 411 cannot together form a condensed aromatic ring, and each occurrence of n411 independently represents an integer from 0 to 4.

8. A composition, containing the compound expressed by General Formula 1 above according to claim 1 .

9. A thin film, containing the compound expressed by General Formula 1 above according to claim 1 .

10. A light-emitting device featuring the organic electroluminescent element according to claim 1 .

11. A display device featuring the organic electroluminescent element according to claim 1 .

12. A lighting device featuring the organic electroluminescent element according to claim 1 .

13. A compound expressed by General Formula 1

wherein X represents an oxygen atom or a sulfur atom, R 111 to R 126 represent each independently a hydrogen atom or a substituent, and Ar 111 is represented by one of General Formulae (1-3) to (1-5) below:

wherein each occurrence of R 411 independently represents hydrogen or a substituent, with the proviso that two or more of the substituents expressed by R 411 cannot together form a condensed aromatic ring, and each occurrence of n411 independently represents an integer from 0 to 4.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 9, 2014
From: WATANABE, KOUSUKE; SOTOYAMA, WATARU
To: UDC IRELAND LIMITED
Reel/Frame 032178/0167 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 6, 2013
From: FUJIFILM CORPORATION
To: UDC IRELAND LIMITED
Reel/Frame 029760/0235 →
Priority Claims (1)
JP 2010-173184 · Jul 30, 2010 · national
Continuity (1)
Related Publication 20130320312A1 · Dec 5, 2013