Dibenzoheterocyclic compound and preparation method and application thereof
A dibenzoheterocyclic compound wherein band gaps of HOMO and LUMO energy levels of the dibenzoheterocyclic compound are wide, light can be emitted in a deep blue light-emitting region; and the LUMO energy level of the dibenzoheterocyclic compound is low, so the LUMO energy level matches with an electron transport layer for electrons injection and transport. The dibenzoheterocyclic compound has hole transport performance, so as a light-emitting layer material, the dibenzoheterocyclic compound balances the ratio of electrons to holes in a light-emitting layer increasing the combination probability and improving the device light-emitting efficiency. The spatial configuration of the dibenzoheterocyclic compound avoids material stacking molecules, reduces annihilation of excitons, and inhibits efficiency roll-off. The dibenzoheterocyclic compound has thermal stability, so deep blue light can be emitted efficiently and stably. With an organic light-emitting diode and a deep blue light-emitting device with high light-emitting efficiency, low working voltage can be obtained.
1. A dibenzoheterocyclic compound, having a structure as shown in a formula (I):
wherein Ar 1 and Ar 2 are, each independently, selected from unsubstituted C 4 -C 60 aryl group;
Y 1 -Y 8 are, each independently, selected from hydrogen, and cyano group, Y 9 -Y 10 are bonded to form a ring B 1 , and the ring B 1 is selected from substituted or unsubstituted imidazole ring.
2. The dibenzoheterocyclic compound according to claim 1 , having a structure as shown below:
3. A preparation method of the dibenzoheterocyclic compound according to claim 1 , wherein
synthesis steps of the dibenzoheterocyclic compound shown in the formula (I) are as follows:
taking a compound shown in the formula (A) as a starting material, performing halogenating reaction under the action of a catalyst to obtain an intermediate 1, and enabling the intermediate 1 to react with triphenylphosphine to generate an intermediate 2; enabling the intermediate 2 and a compound shown in the formula (B) to be subjected to Wittig reaction to obtain an intermediate 3; enabling the intermediate 3 and a compound shown in the formula (C) to be subjected to condensation reaction to obtain an intermediate 4; enabling the intermediate 4 to react with a compound of at least one of Y 1 -Y 8 to generate an intermediate 4-A;
when at least one of Y 9 and Y 10 is not hydrogen, enabling the intermediate 4-A to be subjected to oxidation reaction to obtain an intermediate 5, and enabling the intermediate 5 to react with a cyclic compound forming Y 9 and Y 10 to obtain the dibenzoheterocyclic compound shown in the formula (I);
X 1 -X 3 are, each independently, selected from halogen; X 4 is oxygen; and R 1 -R 8 are, each independently, selected from halogen or hydrogen;
a synthesis route of the dibenzoheterocyclic compound shown in the formula (I) is as follows:
4. The dibenzoheterocyclic compound according to claim 1 , wherein the dibenzoheterocyclic compound is an organic electroluminescent material.
5. An organic light emitting diode, wherein at least one functional layer of the organic light emitting diode contains the dibenzoheterocyclic compound according to claim 1 .
6. The organic light emitting diode according to claim 5 , wherein the functional layer is a light-emitting layer.
7. The organic light emitting diode according to claim 5 , wherein a light-emitting layer material comprises a host material and a guest light-emitting material, and the guest light-emitting material is the dibenzoheterocyclic compound.
8. The organic light emitting diode according to claim 5 , wherein a light-emitting layer material comprises a host material and a guest light-emitting dye, and the host material is the dibenzoheterocyclic compound.
9. The organic light emitting diode according to claim 5 , wherein the organic light emitting diode is a blue light-emitting device.
10. A display unit, comprising the organic light emitting diode according to claim 5 .