Heterocyclic derivative and organic electroluminescent device thereof
Provided are a heterocyclic derivative and an organic electroluminescent device thereof, which relates to the field of organic photoelectric materials. The heterocyclic derivative of Formula I has high electron mobility and great hole blocking performance, and thus the organic electroluminescent device prepared by using the heterocyclic derivative as the electron transport region material, especially the hole blocking material, has low drive voltage and high luminous efficiency. The organic electroluminescent device can also include a hole transport region, and the hole transport region, especially the emissive auxiliary layer, contains the triarylamine compound of Formula II. Since the electron transport region and the hole transport region of the device can effectively balance carriers, which reduces the quenching of excitons and improves the recombination probability of carriers, the device shows low drive voltage and high luminous efficiency.
1. A heterocyclic derivative, having a structure as shown in Formula I:
wherein Ar 1 and Ar 2 are identical or different and selected from the following group:
wherein R 0 is selected from one of hydrogen, deuterium, halogen, cyano, nitro, C1 to C30 alkyl, C3 to C30 cycloalkyl, C6 to C60 aryl or C3 to C60 heteroaryl,
X 0 is selected from one of O, S, N(R x ) or C(R x ) 2 , wherein R x is selected from one of C1 to C30 alkyl, C3 to C30 cycloalkyl, C6 to C60 aryl or C3 to C60 heteroaryl,
Z is selected from C(R y ) or N, wherein R y is selected from one of hydrogen, deuterium, halogen, cyano, nitro, C1 to C30 alkyl, C3 to C30 cycloalkyl, C2 to C30 alkenyl, C2 to C30 alkynyl, C6 to C60 aryl or C3 to C60 heteroaryl, or two adjacent groups are joined to form a ring;
X is selected from one of O, S, N(Art), C(Ar) 2 or Si(Ar) 2 , wherein Ar is selected from one of C1 to C30 alkyl, C3 to C30 cycloalkyl, C6 to C60 aryl or C3 to C60 heteroaryl;
m is selected from 0, 1, 2, 3 or 4, and R is identically or differently selected from one of deuterium, cyano, nitro, C1 to C30 alkyl, C3 to C30 cycloalkyl, C2 to C30 alkenyl, C2 to C30 alkynyl, C6 to C60 aryl or C3 to C60 heteroaryl, or two adjacent groups are joined to form a ring;
L x and L y are independently selected from one of a single bond, C1 to C30 alkylene, C1 to C30 cycloalkylene, C6 to C60 arylene or C3 to C60 heteroarylene; and
L 1 and L 2 are independently selected from one of a single bond, C6 to C60 arylene or C3 to C60 heteroarylene;
wherein said alkyl, cycloalkyl, aryl, heteroaryl, alkenyl, alkynyl, alkylene, cycloalkylene, arylene, and heteroarylene are unsubstituted or substituted with at least one substituent selected from deuterium, halogen, cyano, nitro, C1 to C30 alkyl, C3 to C30 cycloalkyl, C6 to C60 aryl, C3 to C60 heteroaryl and C6 to C60 amine.
2. The heterocyclic derivative according to claim 1 , wherein L x and L y are independently selected from one of a single bond, adamantylene, camphanylene, norbornylene, phenylene, biphenylene, terphenylene, naphthylene, phenanthrylene, triphenylenylene, fluorenylene, benzofluorenylene, spirodifluorenylene, benzospirodifluorenylene, dibenzofuranylene, dibenzothiophenylene, carbazolylene, quinolinylene, isoquinolinylene, naphthyridinylene, quinoxalinylene, quinazolinylene or phenanthrolinylene; and
L 1 and L 2 are independently selected from a single bond or one of the following groups:
wherein T is identically or differently selected from N or C(R m ), wherein R m is selected from one of hydrogen, deuterium, cyano, nitro, C1 to C30 alkyl, C3 to C30 cycloalkyl, C6 to C60 aryl C3 to C60 heteroaryl;
Y is selected from O, S, N(R n ) or C(R n ) 2 , wherein R n is selected from one of hydrogen, deuterium, C1 to C30 alkyl, C3 to C30 cycloalkyl, C2 to C30 alkenyl, C2 to C30 alkynyl, C6 to C60 aryl or C3 to C60 heteroaryl, or two adjacent groups are joined to form a ring; and
L 0 is identically or differently selected from one of a single bond, C6 to C60 arylene or C3 to C60 heteroarylene.
3. The heterocyclic derivative according to claim 1 , wherein Ar 1 and Ar 2 are independently selected from one of the following groups:
4. The heterocyclic derivative according to claim 1 , wherein L 1 and L 2 are independently selected from a single bond or one of the following groups:
5. The heterocyclic derivative according to claim 1 , selected from the following compounds:
6. An organic electroluminescent device, comprising an anode, an organic layer, and a cathode, wherein the organic layer is disposed between the anode and the cathode, and the organic layer comprises an electron transport region containing the heterocyclic derivative according to claim 1 .
7. The organic electroluminescent device according to claim 6 , wherein the organic layer further comprises a hole transport region containing a triarylamine compound as shown in Formula II:
wherein A and B are independently selected from one of the following substituents:
wherein R a is identically or differently selected from one of hydrogen, deuterium, C1 to C15 alkyl, C3 to C15 cycloalkyl, C2 to C30 alkenyl, C6 to C30 aryl or C3 to C30 heteroaryl, or two adjacent groups are joined to form a ring;
R b is identically or differently selected from one of hydrogen, deuterium, C1 to C15 alkyl, C3 to C15 cycloalkyl, C2 to C30 alkenyl, C6 to C30 aryl or C3 to C30 heteroaryl, or two adjacent groups are joined to form a ring;
L a is selected from one of a single bond, C6 to C30 arylene or C3 to C30 heteroarylene;
a is selected from 0, 1, 2, 3 or 4, and b is selected from 0, 1, 2, 3, 4 or 5; and
C is selected from one of the following groups:
wherein R 12 is selected from one of methyl, ethyl, propyl, butyl, phenyl, tolyl, biphenyl or naphthyl;
R 13 is selected from one of deuterium, methyl, ethyl, propyl, butyl, cyclohexyl, adamantyl, phenyl, tolyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, triphenylenyl, acridyl, spirodifluorenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9-phenylcarbazolyl, pyrenyl, indolyl, benzothiophenyl, benzofuranyl, dibenzothiophenyl or dibenzofuranyl;
L b is selected from one of a single bond, phenylene, deuterated phenylene, deuterated naphthylene, tolylene, biphenylene, naphthylene, terphenylene, dibenzofuranylene, fluorenylene or dibenzothiophenylene; and
c is selected from 0, 1, 2, 3, 4 or 5; d is selected from 0, 1, 2, 3 or 4; e is selected from 0, 1, 2, 3, 4, 5, 6 or 7; f is selected from 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9.
8. The organic electroluminescent device according to claim 7 , wherein C is selected from one of the following groups:
9. The organic electroluminescent device according to claim 7 , wherein R a is independently selected from one of hydrogen, deuterium, methyl, ethyl, propyl, butyl, adamantyl, camphanyl, norbornyl, phenyl, tolyl, biphenyl, triphenyl, naphthyl, anthryl, phenanthryl, triphenylenyl, acridinyl, spirodifluorenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9-phenylcarbazolyl, pyrenyl, indolyl, benzothiophenyl, benzofuranyl, dibenzothiophenyl or dibenzofuranyl, or two adjacent groups are joined to form a ring;
L a is selected from one of a single bond, phenylene, tolylene, biphenylene, naphthylene, terphenylene, dibenzofuranylene, fluorenylene or dibenzothiophenylene; and
R b is identically or differently selected from one of hydrogen, deuterium, methyl, ethyl, propyl, butyl, adamantyl, camphanyl, norbornyl, phenyl, tolyl, biphenyl or triphenyl, or two adjacent groups are joined to form a ring.
10. The organic electroluminescent device according to claim 7 , wherein the triarylamine compound as shown in Formula II is selected from one of the following structures: